Jesse: I have a friend who is king nerd of the Minneapolis sound. Just one of the greatest nerds of every tributary of that river—not least of which is your work. And he heard I was doing this interview and he sent me this stem that I wanted to play. So, this is from—and just ‘cause I just loved hearing it. So, first I wanna play a little bit of a hit that you guys made with Janet Jackson called “Love Would Never Do Without You”.
[Love Would Never Do plays]
Jesse: So, like, when I hear that record, I hear a lot of the—a lot of the kind of signatures of the especially kind of upbeat records that you made with Janet Jackson. Right? Janet has this beautiful—this beautiful light voice that always feels like it’s flying no matter what she’s singing. And you’re backing that up with those—you know, with those hard drums. You know, boom-BOP! You know? But he sent me—the stem that he sent me, and he like—he sent me a timecode. He wanted me to hear this particular—was the synth. Just halfway through the record. So, I just wanna play a little bit of that.
[plays the funkiest organ riff you've ever heard in your goddamn life]
Jesse: So, I gotta take us out of that or else I’ll just—
Terry: Ooooh, that’s funky.
Jesse: I’ll just listen to it all day long.
Jimmy: Yeah. That was my—that was my attempt at Sly and the Family Stone, right there. [Jesse and Terry laugh.] But played on a—played on a—played on an OB-8. That’s an OB-8 organ. It’s—A5 is the setting on the OB-8, on the original settings, that’s what that is. I know exactly the sound. That’s funky.
Jesse: What’s wild to me about that is that that is like a complimentary piece in this song. Right? Like, as I described, like as a casual listener to that hit record, I’m hearing Janet and I’m hearing that drum track. You know? And I’m hearing choruses of vocals. You know, you’ve got the kind of big call and response-y type deal going on. You know, there’s a lot of things going on in that song. And that part [chuckling] is so distinctive and so funky and it’s just in there. You know what I mean? Like, it’s just a piece of the puzzle.
Jimmy: It’s—yeah. You know, that’s the seasoning. When I—when we do—I talk all the time about the seasoning and stuff. It’s like when you cook in the kitchen. Right? You know, when you taste the food, you just taste it and it either tastes good or it doesn’t taste good. But if you’re an actual chef when you taste the food, you’re not only tasting that it tastes good overall, but you’re also deciphering all of the seasonings that are in there. So, that organ part is one of those things that you don’t necessarily hear it, but you feel it. Like if you take it out, it doesn’t feel the same. Like a certain spice, if you take it out, it doesn’t taste the same. Andi it’s not even that you’re tasting the spice, but you can taste when it’s not there. I love music nerds, because I’m a music nerd myself and I love when there’s things in there that only music nerds would ever hear or appreciate what they are. Because I just think it’s important. And I think to the casual listener—like I say, they don’t know that it’s there, but they know the way that it makes them feel when they hear it. You know? So, that’s cool. I—that’s awesome. I haven’t heard that part broken out like that before, either. So, that’s very cool.
The reason this conversation (and this riff!) stuck with me so much is because it speaks to the care, and the craft, and the belief that people will really hear what you're doing, even years or decades later, and know the love and the funk and the soul that went into making something.
Early the covid pandemic, when everyone was hanging out on Instagram live listening to DJ sets, I found myself listening in the wee hours of the night to one of Questlove's DJ sets, and reflecting on some of the beautiful details that buried in the mix. In doing so, I said that sometimes you have to "squint your ears", and one of the people who reacted most enthusiastically to that conversation was Jimmy Jam, who understood instinctively that this was just another way of getting to what he calls here the "right spices" to have in the mix.
I've constantly been inspired by someone like Jimmy because he can operate both at the most foundational level of being a brilliant working musician who instinctively knows how to make a timeless groove, and he can be one of the most effective and influential executives in the entire recording industry by leading the Recording Academy. Being able to keep the head and the heart so closely in sync while pursuing a legendary career and never, ever compromising is honestly the dream.
And being able to seamlessly articulate why he had such a funky little gift hidden for us in one of Janet's greatest songs gives me so much hope that maybe the rest of us can create that kind of greatness too.
From 2019: After the Rhythm Nation
]]>In the year @JanetJackson finally will take her overdue place in the @rockhall an interesting perspective and good read from @anildash after the #RhythmNation #JanetJackson #JimmyJam #TerryLewis https://t.co/eU5OpzQGGK
— Jimmy Jam (@flytetymejam) January 3, 2019
And the thing is, like a lot of taboos or loosely-defined cultural norms, the "selling out" meme was about enforcing a set of social values within a community, values that came to seem downright quaint by the start of the 2020s. My germinal understanding of what "selling out" meant came in the moment when Baby Booomers truly claimed their cultural dominance, and the then-young Gen X began to form its countercultural identity. In 1987, The Beatles' "Revolution" was used in a Nike advertisement. And everybody lost their shit. This seems like an absurd thing to say in the current environment, where most of the biggest music acts in the world have their own multifaceted clothing lines, but fans were aghast at the idea that True Art could be used in the service of mere commerce. (This was also how a lot of people found out about Michael Jackson's ownership stake in the Beatles' publishing rights.)
I thought for sure I had misremembered what Time wrote about the event back then, but no, my childhood memory served me — the weekly newsmagazine of record really did compare Michael Jackson to John Lennon's murderer in criticizing his role in permitting a Beatles song to be used in a sneaker ad.
The fundamentally anticommercial stance of sellout anxiety, especially in regard to music's role in popular culture, only got sharper over the next several years. By the time Alt Rock was designated as the only critically-acceptable music in the early 90s, you had Kurt Cobain working full time to signify in every way possible that he hadn't sold out, even when on the cover of mainstream magazines. But the boundaries of what constituted "selling out" were always fuzzy, and contingent on the larger context of how an artist operated; there was a bright-line distinction between serious artists (Dylan, Springsteen, other mostly-white dudes) and disposable pop acts, who were allowed to transgress on these grounds.
The peak of the sellout reckoning was likely in 1994, when the concern expanded from theoretical debates about rock stars to what felt like a daily ongoing consideration for an entire generation. This, too, was captured in popular culture, as in films like that year's Reality Bites, where a central animating tension of the film is Winona Ryder having to choose between two different assholes, ultimately picking the one who hasn't sold out within the film's narrative.
In contemporary culture, the "sellout" character's framing as a villain would likely be incoherent to many. The sin that he commits is to sell his own creation to a platform that can offer it distribution. At a time when artists structure the rollout of their ancillary product offerings to coincide with the release of their ostensible creative works (music, films, shows), being savvy about getting work in front of an audience would be difficult to portray as an act of villainy.
I've been ruminating on this for years in this space; almost 20 years ago, Bob Dylan endorsed Victoria's Secret after decades of hinting that he'd do exactly that, and his fanbase was scandalized. I was more concerned that he was inaccurately associated with a campaign called "very sexy", but clearly the implications of a stalwart of anticommercialism embracing such a nakedly opportunistic campaign was bewildering to those who analyze such things.
By the time Beyoncé began working House of Deréon nods into her song lyrics, I realied that the sellout narrative that I had grown up being coached in was anachronistic, and disconnected from culture overall, but especially from the increasing diversity of mainstream American culture. As a Prince fan, I'd spent decades listening to him talk about ownership and equity of his work in the context of centuries of exploitation of Black artists: "If u don't own your masters, then your masters own u." This was primarily a narrative about control and agency, but it was not an anticommercial message, even if it contained an implicit critique of capitalism.
This tension over conflating control (and commercial success) with agency and genuine empowerment got more complicated in every aspect of society over the early 2000s and into the 2010s, with the rise of girlboss-ism and LLC grindbros demonstrating the vacuous end stage of those for whom nothing could ever be selling out. Bethany Klein ably documented this in both her research and in interviews like the one linked here. There's been an acceleration of commercial appropriation of culture as the venture capital business model takes over more and more creative industries.
So it should have been no surprise, then, when the concern over selling out in the early 2000s even rose to the surface in the technology industry where I'd been working. Though I hadn't been consciously aware of it, the early social web community I came from had inherited some of the academia-adjacent norms of the early internet, where commercial interests were (rightly) seen with deep skepticism.
Amongst those who built the first blogging tools and social networks, it was taken as a given that one would hate banner ads, or resist the control of the then-dominant tech giants of the day, like Microsoft and AOL. This will, again, seem quaint, but when we hamhandedly asked our customer base to pay for Movable Type (an early blogging tool that I had helped launch), the blowback from users was so swift, and so ferocious, that skimming through the responses left me sitting at my desk with tears in my eyes. Part of it was that almost no one had ever faced a social media shitstorm before (these are the perils that come with inventing the tools which allow these things to happen) and part of it was that all we had done was ask people to buy an app and now we were getting death threats. Later, a lot of the most vociferous critics would embrace the "If you aren't paying for the product, you are the product" anthem of experienced internet skeptics, but in that early era of the social web, the overwhelming critique was simple: we had sold out.
By just a few years later, many of people who had been most vociferous in those early, commerce-skeptical communities suddenly popped up working at these new tech titans, usually with a half-sheepish blog post ironically mentioning how they had sold out. Under their tenures, the most pervasive and destructive new tech platforms grew into giants. They stopped blogging about it after a while.
Sometime around 2016, before the election that never ended and the beginning of the tedious online battles that refuse to die, I noticed that mainstream culture had gotten back its skepticism over nakedly corporate profiteering. Whether it was the rise of a revitalized labor movement, justified fury at the ways income inequality had made the former milestones of young adulthood unattainable, watching good people die because they couldn't crowdfund healthcare, or just a simple desire for fairness, it was refreshing to see this critical view pop back up, after decades where I'd feared nobody would ever return to articulating the positive values that underpinned the "selling out" narrative.
Those of us who were old enough to remember when Reagan fired the air traffic controllers, or to have had parents who were union members at a time when the default public sympathies were with workers, still find it surprising and delightful to hear young people identify as socialists, and honestly it's a joy to hear hack writers working in ham-handed swipes at capitalism into mainstream comedy bits. Thanks to parenthood, I regularly spend time around tweens, and they'll routinely (and rightly) blame capitalism for systemic problems, and sometimes absurdly use it as a punchline for more quotidian problems as well.
But what these kids are telling each other, in their own way, is "Don't sell out." The humanist, principled point of view that pushed people to rein in their most avaricious impulses is now fully back in vogue amongst the people shaping culture, and it's a joy to watch. Even better, the tedious aspects of its prior incarnations, like gatekeeping and eye-rolling purity tests, have largely been left by the wayside; people are pragmatic about the compromises that we all must make to get by these days, but they still hold high standards about considering the ethical and social aspects of how we move through the world — and they expect the artists, activists, leaders and voices that they support to do the same as well.
I don't know if anyone will ever call it "selling out" again; it's an anachronistic term, tied to the fading days of boomer cultural dominance. But even if it played out in insufferable ways (I genuinely do not give a fuck if a Beatles song is in a sneaker commercial), I am truly glad to have formed my point of view on culture and society at a time when there was a peer-based expectation of having values, and of holding each other to them. That's what community is; that's what people do for each other.
And the new, more supportive, more nuanced and informed view of that impulse is a wonderful upgrade. May you never be a sellout.
]]>But we can tell the traditional tech industry (the handful of giant tech companies, along with startups backed by the handful of most powerful venture capital firms) is in the midst of building another "Web3"-style froth bubble because they've again abandoned one of the core values of actual technology-based advancement: reason.
I don't say this lightly, I say this with purpose. Amongst engineers, coders, technical architects, and product designers, one of the most important traits that a system can have is that one can reason about that system in a consistent and predictable way. Even "garbage in, garbage out" is an articulation of this principle — a system should be predictable enough in its operation that we can then rely on it when building other systems upon it.
This core concept of a system being reason-able is pervasive in the intellectual architecture of true technologies. Postel's Law ("Be liberal in what you accept, and conservative in what you send.") depends on reasonable-ness. The famous IETF keywords list, which offers a specific technical definition for terms like "MUST", "MUST NOT", "SHOULD", and "SHOULD NOT", assumes that a system will behave in a reasonable and predictable way, and the entire internet runs on specifications that sit on top of that assumption.
The very act of debugging assumes that a system is meant to work in a particular way, with repeatable outputs, and that deviations from those expectations are the manifestation of that bug, which is why being able to reproduce a bug is the very first step to debugging.
Into that world, let's introduce bullshit. Today's highly-hyped generative AI systems (most famously OpenAI) are designed to generate bullshit by design. To be clear, bullshit can sometimes be useful, and even accidentally correct, but that doesn't keep it from being bullshit. Worse, these systems are not meant to generate consistent bullshit — you can get different bullshit answers from the same prompts. You can put garbage in and get... bullshit out, but the same quality bullshit that you get from non-garbage inputs! And enthusiasts are current mistaking the fact that the bullshit is consistently wrapped in the same envelope as meaning that the bullshit inside is consistent, laundering the unreasonable-ness into appearing reasonable.
Now we have billions of dollars being invested into technologies where it is impossible to make falsifiable assertions. A system that you cannot debug through a logical, socratic process is a vulnerability that exploitative tech tycoons will use to do what they always do, undermine the vulnerable.
So, what can we do? A simple thing for technologists, or those who work with them, to do is to make a simple demand: we need systems we can reason about. A system where we can provide the same input multiple times, and the response will change in minor or major ways, for unknown and unknowable reasons, and yet we're expected to rebuild entire other industries or ecosystems around it, is merely a tool for manipulation.
Narcissists and abusers use the inconsistent and capricious changing of responses as a way of controlling and manipulating their victims. They are unreasonable because it is an effective way to keep the vulnerable in a place where they constantly have to respond, or where they have to live in a constant state of fear and anticipation about how they will be expected to react. Technologies are created by people, and systems reflect the values of their creators.
We should react to unreasonableness in purported technologies in the same way we react to intentional unreasonableness in people in positions of power: set firm boundaries, be ready to walk away, don't debate, demand consistent and reasonable behavior.
]]>As I've been saying for a while, and as Krugman quotes, "it's impossible to overstate the degree to which many big tech CEOs and venture capitalists are being radicalized by living within their own cultural and social bubble." Many people resist believing this can be the case, because we've been fed so much of the "Great Man" myth, and are told so often to believe in these people as the innovators and brilliant minds that will bring us to some exciting promised future.
But I've spent decades in this industry, often knowing the executives and investors long before they came to wield so much power, and... they're just a bunch of dudes. They're just as prone to becoming swept up in stupid conspiracized thinking as, well, everyone else in their demographic seems to have been. And it's important to remember, nobody becomes a billionaire by accident. You have to have wanted that level of power, control and wealth more than you wanted anything else in your life. They all sacrifice family, relationships, stability, community, connection, and belonging in service of keeping score on a scale that actually yields no additional real-world benefits on the path from that first $100 million to the tens of billions.
So you have a cohort that is, counterintutively, very easily manipulated. If you have access to a billionaire (and billionaires all have access to each other, because it suits their ego to think of each other as peers), most are very easy to program by simply playing to their insecurity and desire for acknowledgement of exceptionalism, and so they push each other further and further into extreme ideas because their entire careers have been predicated on the idea that they're genius outliers who can see things others can't, and that their wealth is a reward for that imagined merit. "I must be smart, look how rich I am." The rising power of movements meant to counter their influence has catalyzed a vicious, and frankly very weird, backlash where they want to put everyone else in their place. And, due to the insularity of their lifestyles, they very seldom have any corrective voices pointing out when they've clearly lost the plot. If it weren't for the deep harm they were doing to so many with these radical ideas, I'd have a lot of pity and empathy for the fact that they're clearly acting out due to social isolation and the existential emptiness that must come from pursuing wealth and power to such an extreme degree that there's no room left in life for someone to call them on their bullshit.
But, since the first step to fixing any problem is being able to clearly identify it, I'm gratified to hear more people recognizing the social and cultural factors that are shaping the otherwise-inexplicable choices of some of the most powerful people in the business world. Now here's hoping that those outside the bubble can gather together and organize an effective counter-response to the increasing dangers and harms posed by the radicalization of the loudest voices in tech.
]]>This is thanks (once more) to Malaika Handa, seen previously in one of my earlier crossword appearances. Yes, this somehow happens fairly regularly.
]]>That morning, there were so many moments I was hopeful. First, it was just an accident. Next, that everyone could escape the towers if given the chance. Then, that only one tower would fall. Then, that these would be the only casualties. Then, worst of all, that something this profound and dramatic would soften people's hearts and make them reflect.
I was wrong, over and over again. I don't know exactly where the line is between optimistic and naive, but these days I feel tremendous compassion and empathy towards the young man who had all those foolish beliefs. I don't regret hoping that such a horrible day could lead to something better.
But I really did underestimate how power works, and how little it would take to push people from their better angels to their most vicious, vengeful selves. I did not expect that the story of this city I love so much, in a moment we all felt so vividly, would just become a bludgeon used by those who hated and resented us just as much as the perpetrators of that day's violence.
So maybe I keep coming back because I am hoping that others might still recognize the little glimpses of humanity that I saw on the day of the attacks, and that I saw in abundance, in New York City, in the days that follow. It wasn't a myth, it wasn't just wishful thinking, there really was kindness and care in this place that I love so much. I don't think those who tell the loudest stories today would even recognize it.
Last year, "There Is Nothing To Remember"
So it's clear that the events of that day have fully passed into myth, useful only as rhetoric in a culture war, or as justifications for violence. Nothing epitomizes this more than the fact that, while the memory has faded in culture broadly, it's only brought to the fore in situations like those where most New Yorkers would be targeted.
Two years ago, "Twenty is a Myth":
I can't change how society overall sees this event. To my eternal regret, I couldn't change how we responded in any meaningful way. But I did get to make personal changes, permanently and for the better, and the loss and grief of that day does still motivate me to try to honor the moment by pushing for justice, and care, and an earnest engagement with the world.
Three years ago, Nineteen is When They Forgot
I do have the experience of having seen this city bounce back from unimaginable pain before. I have seen us respond to attacks on our public life by rebuilding and reimagining public space. I have seen us grieve our losses and rally behind those who cared for those injured, and preserve space in our cultural memory for their pain and sacrifice. By no means have we done enough for all those lost, but it is absolutely true that we can rebuild. We’ve done it before.
Four years ago, Eighteen is History
There are ritualized remembrances, largely led by those who weren't there, those who mostly hate the values that New York City embodies. The sharpest memories are of the goals of those who masterminded the attacks. It's easy enough to remember what they wanted, since they accomplished all their objectives and we live in the world they sought to create. The empire has been permanently diminished. Never Forget.
In 2018, Seventeen is (Almost) Just Another Day
I spent so many years thinking “I can’t go there” that it caught me completely off guard to realize that going there is now routine. Maybe the most charitable way to look at it is resiliency, or that I’m seeing things through the eyes of my child who’s never known any reality but the present one. I'd spent a lot of time wishing that we hadn't been so overwhelmed with response to that day, so much that I hadn''t considered what it would be like when the day passed for so many people with barely a notice at all.
In 2017, Sixteen is Letting Go Again
So, like ten years ago, I’m letting go. Trying not to project my feelings onto this anniversary, just quietly remembering that morning and how it felt. My son asked me a couple of months ago, “I heard there was another World Trade Center before this one?” and I had to find a version of the story that I could share with him. In this telling, losing those towers was unimaginably sad and showed that there are incredibly hurtful people in the world, but there are still so many good people, and they can make wonderful things together.
In 2016 Fifteen is the Past:
I don’t dismiss or deny that so much has gone so wrong in the response and the reaction that our culture has had since the attacks, but I will not forget or diminish the pure openheartedness I witnessed that day. And I will not let the cynicism or paranoia of others draw me in to join them.
What I’ve realized, simply, is that 9/11 is in the past now.
In 2015, Fourteen is Remembering:
For the first time, I clearly felt like I had put the attacks firmly in the past. They have loosened their grip on me. I don’t avoid going downtown, or take circuitous routes to avoid seeing where the towers once stood. I can even imagine deliberately visiting the area to see the new train station.
In 2014, Thirteen is Understanding:
There’s no part of that day that one should ever have to explain to a child, but I realized for the first time this year that, when the time comes, I’ll be ready. Enough time has passed that I could recite the facts, without simply dissolving into a puddle of my own unresolved questions. I look back at past years, at my own observances of this anniversary, and see how I veered from crushingly sad to fiercely angry to tentatively optimistic, and in each of those moments I was living in one part of what I felt. Maybe I’m ready to see this thing in a bigger picture, or at least from a perspective outside of just myself.
From 2013, Twelve is Trying:
I thought in 2001 that some beautiful things could come out of that worst of days, and sure enough, that optimism has often been rewarded. There are boundless examples of kindness and generosity in the worst of circumstances that justify the hope I had for people’s basic decency back then, even if initially my hope was based only on faith and not fact.
But there is also fatigue. The inevitable fading of outrage and emotional devastation into an overworked rhetorical reference point leaves me exhausted. The decay of a brief, profound moment of unity and reflection into a cheap device to be used to prop up arguments about the ordinary, the everyday and the mundane makes me weary. I’m tired from the effort to protect the fragile memory of something horrific and hopeful that taught me about people at their very best and at their very, very worst.
In 2012, Eleven is What We Make:
These are the gifts our children, or all children, give us every day in a million different ways. But they’re also the gifts we give ourselves when we make something meaningful and beautiful. The new World Trade Center buildings are beautiful, in a way that the old ones never were, and in a way that’ll make our fretting over their exorbitant cost seem short-sighted in the decades to come. More importantly, they exist. We made them, together. We raised them in the past eleven years just as surely as we’ve raised our children, with squabbles and mistakes and false starts and slow, inexorable progress toward something beautiful.
In 2011 for the 10th anniversary, Ten is Love and Everything After:
I don’t have any profound insights or political commentary to offer that others haven’t already articulated first and better. All that I have is my experience of knowing what it mean to be in New York City then. And from that experience, the biggest lesson I have taken is that I have the obligation to be a kinder man, a more thoughtful man, and someone who lives with as much passion and sincerity as possible. Those are the lessons that I’ll tell my son some day in the distant future, and they’re the ones I want to remember now.
In 2010, Nine is New New York:
[T]his is, in many ways, a golden era in the entire history of New York City. Over the four hundred years it’s taken for this city to evolve into its current form, there’s never been a better time to walk down the street. Crime is low, without us having sacrificed our personality or passion to get there. We’ve invested in making our sidewalks more walkable, our streets more accommodating of the bikes and buses and taxis that convey us around our town. There’s never been a more vibrant scene in the arts, music or fashion here. And in less than half a decade, the public park where I got married went from a place where I often felt uncomfortable at noontime to one that I wanted to bring together my closest friends and family on the best day of my life. We still struggle with radical inequality, but more people interact with people from broadly different social classes and cultures every day in New York than any other place in America, and possibly than in any other city in the world.
And all of this happened, by choice, in the years since the attacks.
In 2009, Eight Is Starting Over:
[T]his year, I am much more at peace. It may be that, finally, we’ve been called on by our leadership to mark this day by being of service to our communities, our country, and our fellow humans. I’ve been trying of late to do exactly that. And I’ve had a bit of a realization about how my own life was changed by that day.
Speaking to my mother last week, I offhandedly mentioned how almost all of my friends and acquaintances, my entire career and my accomplishments, my ambitions and hopes have all been born since September 11, 2001. If you’ll pardon the geeky reference, it’s as if my life was rebooted that day and in the short period afterwards. While I have a handful of lifelong friends with whom I’ve stayed in touch, most of the people I’m closest to are those who were with me on the day of the attacks or shortly thereafter, and the goals I have for myself are those which I formed in the next days and weeks. i don’t think it’s coincidence that I was introduced to my wife while the wreckage at the site of the towers was still smoldering, or that I resolved to have my life’s work amount to something meaningful while my beloved city was still papered with signs mourning the missing.
In 2008, Seven Is Angry:
Finally getting angry myself, I realize that nobody has more right to claim authority over the legacy of the attacks than the people of New York. And yet, I don’t see survivors of the attacks downtown claiming the exclusive right to represent the noble ambition of Never Forgetting. I’m not saying that people never mention the attacks here in New York, but there’s a genuine awareness that, if you use the attacks as justification for your position, the person you’re addressing may well have lost more than you that day. As I write this, I know that parked out front is the car of a woman who works in my neighborhood. Her car has a simple but striking memorial on it, listing her mother’s name, date of birth, and the date 9/11/2001.
In 2007, Six Is Letting Go:
On the afternoon of September 11th, 2001, and especially on September 12th, I wasn’t only sad. I was also hopeful. I wanted to believe that we wouldn’t just Never Forget that we would also Always Remember. People were already insisting that we’d put aside our differences and come together, and maybe the part that I’m most bittersweet and wistful about was that I really believed it. I’d turned 26 years old just a few days before the attacks, and I realize in retrospect that maybe that moment, as I eased from my mid-twenties to my late twenties, was the last time I’d be unabashedly optimistic about something, even amidst all the sorrow.
In 2006, After Five Years, Failure:
[O]ne of the strongest feelings I came away with on the day of the attacks was a feeling of some kind of hope. Being in New York that day really showed me the best that people can be. As much as it’s become cliché now, there’s simply no other way to describe a display that profound. It was truly a case of people showing their very best nature.
We seem to have let the hope of that day go, though.
In 2005, Four Years:
I saw people who hated New York City, or at least didn’t care very much about it, trying to act as if they were extremely invested in recovering from the attacks, or opining about the causes or effects of the attacks. And to me, my memory of the attacks and, especially, the days afterward had nothing to do with the geopolitics of the situation. They were about a real human tragedy, and about the people who were there and affected, and about everything but placing blame and pointing fingers. It felt thoughtless for everyone to offer their response in a framework that didn’t honor the people who were actually going through the event.
In 2004, Thinking Of You:
I don’t know if it’s distance, or just the passing of time, but I notice how muted the sorrow is. There’s a passivity, a lack of passion to the observances. I knew it would come, in the same way that a friend told me quite presciently that day back in 2001 that “this is all going to be political debates someday” and, well, someday’s already here.
In 2003, Two Years:
I spent a lot of time, too much time, resenting people who were visiting our city, and especially the site of the attacks, these past two years. I’ve been so protective, I didn’t want them to come and get their picture taken like it was Cinderella’s Castle or something. I’m trying really hard not to be so angry about that these days. I found that being angry kept me from doing the productive and important things that really mattered, and kept me from living a life that I know I’m lucky to have.
In 2002, I wrote On Being An American:
[I]n those first weeks, I thought a lot about what it is to be American. That a lot of people outside of New York City might not even recognize their own country if they came to visit. The America that was attacked a year ago was an America where people are as likely to have been born outside the borders of the U.S. as not. Where most of the residents speak another language in addition to English. Where the soundtrack is, yes, jazz and blues and rock and roll, but also hip hop and salsa and merengue. New York has always been where the first fine threads of new cultures work their way into the fabric of America, and the city the bore the brunt of those attacks last September reflected that ideal to its fullest.
In 2001, Thank You:
]]>I am physically fine, as are all my family members and immediate friends. I’ve been watching the footage all morning, I can’t believe I watched the World Trade Center collapse…
I’ve been sitting here this whole morning, choking back tears… this is just too much, too big. I can see the smoke and ash from the street here. I have friends of friends who work there, I was just there myself the day before yesterday. I can’t process this all. I don’t want to.
Imagine a mug that's left on a coffee table. If you're on good terms with your roommate, then it's no big deal — "don't sweat it, I've got it!" But if you're not feeling like you're on the same page, then that one dirty mug left out on the table is proof of their fundamental disrespect for the shared space, and for you as a person. The mug is the physical manifestation of their contempt, and of the lack of shared values.
The question is whether our reactions are primed by the prior context that existed when we were entering the situation, and the test is if we can be empathetic enough, and detatched enough, to evaluate the action on its own merits.
]]>Well, things changed a little bit in tech of late. Often, the power shifts in the tech world because of a dramatic new invention that solves an old problem a whole lot better. But in the current era, when most of what's getting funded and hyped up are just various attempts to undermine workers and control consumers, we're instead seeing lots of major players lose power because their signature offerings have gotten so much worse. Search engines are becoming far more useless as they attempt to chase AI hype and shoehorn in less reliable results, even as their legitimate search results get cluttered up with AI-generated crap. The most culturally influential social network has had its cultural relevance destroyed by its billionaire man-child owner's tantrum-based managemenet style. And the major mobile phone platforms overplayed their hand so badly in exerting power over their app ecosystems that regulators around the globe have responded by prying open these heretofore-closed markets.
And all along, lying in wait for a moment just like this, was the weird, wild world wide web.
I've been ecstatic to see the enthusiastic response to "The Internet Is About to Get Weird Again", my first piece for Rolling Stone. (Though I do, of course, lament that this magazine of all publications wouldn't let me have the headline on a piece that went live just before New Year's simply say, "The Internet gets ready to party like it's 1999.")
But by now it's clear, this isn't just wishful thinking on my part, or on the part of the millions of other people who warmly remember the good parts of the way the web used to work. Just over eleven years ago, I wrote "The Web We Lost", which was another surprisingly popular look at the changing dynamics of the mainstream internet. But, though that piece was a call to fight for the open web as a countervailing force to the then-nascent destructive forces that were taking over tech, it really was me mostly trying to be hopeful. (And, as in the related talk I gave at Harvard, trying to teach people about the power dynamics that were truly driving the shifts in the web.) By a few years later, though, I'd largely lost that hope, convinced that the battle had been won by the people who had made the internet a tool for maniupulation and undermining ordinary people's power.
I didn't count on them being such sore winners, though. And I should never have underestimated the passion and resilience of the people who create the good internet, those who never stopped making things just for the love of the medium. It's ironic that I'd forget that, when... well, you're looking at one example of a thing on the web that's been created for 25 years straight purely out of love for this medium.
So, while I'm still circumspect and cautious about the very real threats and harms that will come from the worst parts of the major internet platforms, I am more optimistic than I've been in a long time about the massive potential of the human internet to come roaring back in a way that we haven't seen in a generation. More and more, I think of it as "the people's web". And like so many things that come from, and by, the power of the people, it's a movement that can be delayed, or undermined, but increasingly I have come to believe that it cannot possibly be truly stopped.
I'll end here as I did in the Rolling Stone piece:
I’m not a pollyanna about the fact that there are still going to be lots of horrible things on the internet, and that too many of the tycoons who rule the tech industry are trying to make the bad things worse. (After all, look what the last wild era online lead to.) There’s not going to be some new killer app that displaces Google or Facebook or Twitter with a love-powered alternative. But that’s because there shouldn’t be. There should be lots of different, human-scale alternative experiences on the internet that offer up home-cooked, locally-grown, ethically-sourced, code-to-table alternatives to the factory-farmed junk food of the internet. And they should be weird.]]>
With Meta/Facebook/Instagram moving quickliy to federate their Threads platform into the rapidly-expanding fediverse, many are curious about how they're engaging with the community, and what their strategy might be. Given that sincere interest, it's been remarkable to note that Tom Coates' blog post on Threads' meeting with community members, along with Johannes Ernst's own take, are the definitive perspectives on the way that the industry titan is trying to engage. Both were informed by their direct participation in an otherwise closed-door meeting, with a completely different context than the usually carefully-manicured press events that are used to brief journalists about a product.
It's remarkable that this story wasn't broken by industry trade press (much of which is increasingly captured by the major tech companies, or at least beholden to its constraints of access or embargoes) and wasn't dictated directly by Meta's PR team, but was instead discussed by practitioners who do the actual work of engaging with the community and with the underlying technologies. I can't wait to see the next wave of similar conversations, centered around open formats and the open web, that is driven by conversation amongst and between the personal sites of individual participants — because that's how many of the best innovations of the first era of the social web happened.
]]>Post by @theromanmarsView on Threads
But here's the thing: being able to say, "wherever you get your podcasts" is a radical statement. Because what it represents is the triumph of exactly the kind of technology that's supposed to be impossible: open, empowering tech that's not owned by any one company, that can't be controlled by any one company, and that allows people to have ownership over their work and their relationship with their audience.
See, podcasting as a technology grew out of the early era of the social web, when the norms of technology creators were that they were expected to create open systems, which interoperated with tools by other creators and even other companies. This was based on the successes of earlier generations of the internet, like email and even the web itself. Podcasting was basically the last such invention to become mainstream, with millions of people listening every day, and countless people able to create in the medium. And of course, it creates tons of oppportunities for businesses too, whether it's people making amazing podcasts like Roman Mars does, or giants like Apple or Spotify building businesses around the medium.
Contrast this to other media formats online, like YouTube or Tiktok or Twitch, which don't rely on open systems, and are wholly owned by individual tech companies. On those platforms, creators are constantly chasing the latest algorithmic shifts, and are subject to the whims of advertising algorithms that are completely opaque. If a creator gets fed up enough to want to leave a platform, they're stuck — those viewers or listeners are tied to the company that hosts the content.
But in the podcasting world, creators can (assuming they work out the business deals necessary to do so) actually take their ball and go home, because the underlying "feed" — the special file that podcasting apps look at to know when there's a new episode — is something they can actually move over to a new system or a new host, without losing all their subscribers or followers. Indeed, this idea of having a "portable" audience is so appealing that it's even been revived in the new wave of open format-based social networks that have arisen. When I found out that my Mastodon account was hosted by a company that was kind of shady, I was able to move it over to a Mastodon account run by Medium, and it was basically seamless for my followers, even though I had one of the biggest Mastodon follower counts in the world at the time. That capability is something most podcasters can do if they ever want to, too.
Many times, the value of open technology systems can be measured by which ecosystems they extract dollars away from. Yes, some of the economic value of podcasting came by making a dent in things like terrestrial radio broadcasts. But a big part was also the fact that the open formats of podcasting make it extremely difficult to do the kind of surveillance-based advertising that has made companies like Google and Facebook worth trillions of dollars. In fact, despite their immense scale, neither of the biggest ad-based platforms on the internet can enable you to buy ads on podcasts. In that way, podcasts have reintroduced the wonderful kind of advertising inefficiencies that we saw in the heyday of print magazines, where advertisers were hoping that some part of the audience would mail back one of those blow-in cards that used to be sandwiched into the binding of a magazine. (Kids, ask your grandparents.)
Advertising inefficiencies are fantastic! In the ad industry, the old (likely apocryphal) line one would always hear is, "Half the money I spend on advertising is wasted; the trouble is I don’t know which half." But for creators, and for the world, that inefficiency was often wonderful. The inefficiency of old media formats resulted in less surveillance of the purchasing and behavioral habits of individuals, and larger surpluses that sustained a healthier, more vibrant media ecosystem that could even afford to invest in important stories or content despite the fact that they might not have a large audience.
What podcasting holds in the promise of its open format is the proof that an open web can still thrive and be relevant, that it can inspire new systems that are similarly open to take root and grow. Even the biggest companies in the world can't displace these kinds of systems once they find their audiences. And that's not to say that there aren't shortcomings or problems with these systems, too. But, for example, when someone makes a podcast that's about encouraging hate, there's no one centralized system that can automatically suggest it to an audience and push them down a path of further radicalization.
And of course, the winner-takes-all world of media being consumed by tech means that the economics of individual podcast production are often brutal now, sometimes simply because creators can't rely on outsourcing advertising sales to one of the big platforms. An open system isn't a panacea for all that's broken in the media ecosystem.
But what we can take away from hearing "wherever you find podcasts" at the end of every episode we listen to is that, sometimes without us knowing, radical systems can survive and even thrive in the modern world of tech and media. They can inspire new creators to make similar systems that are unowned, uncentralized, and a little bit uncontrollable. And in this era where we're seeing the renaissance of the open web, they point the way toward a future where we can use the same tone to say "wherever you find news" or "wherever you find your friends online", and know that it means that there's a way that our lives online could be fully in our own control.
]]>This isn't too surprising; we almost never actually teach people how to use the ordinary tools of business communication in more effective ways. So, I'm gathering some advice that I regularly share with people, in hopes that this helps you get your messages across more effectively. All of this is advice that should apply regardless of whether you're using tools like Google Docs (uh... Workspace?), Microsoft Office (or 365 or something?) or whatever else.
The most common, and most serious, problem people have in creating documents is that they don't consider who they're speaking to and what they're trying to accomplish. This can manifest in many ways, but most often the result is an end result that is technically not wrong (things like grammar and spelling may be correct, or the facts and figures may be accurate) but that is completely ineffective in achieving its goals. Ask yourself a few questions:
There are more questions in this vein, but what you'll find as a unifying thread amongst all these questions is starting from a standpoint of asking about empathy and perspective. If you don't do this, your output is a failure before it's even shared, but if you get most of these right, any gaps or shortcomings are likely to be addressed in a collaborative way, because the thought and care behind the work will be evident.
The most common failure cases I see in these kinds of situations is people starting from deep within their own heads, either because they've been fully immersed in a particular project, or because they're reacting to their own fears or concerns. (Even if those are legitimate!) I can't tell you how many times I've seen an important document, like a cover letter for a job, or a pitch for fundraising, that essentially starts with a lengthy, off-putting, deeply insular recitation of a list of things that are basically a litany of the author's insecurities. Don't do this!
Start from common ground, identify the shared goal that you and your audience have, name the ways in which you're already on the path together, highlight what remains to be done, and then close by asking for their help (in whatever form) for you all to keep progressing on your collective goal.
This classic from Joey Cherdarchuk at Dark Horse Analytics has been kicking around for a full decade, and I still end up sending it to someone about once a week.
If I had one bit of advice that I'd build into these tools, it would be this: Stop overusing formatting! Look at the formatting bar, and ignore almost all of the buttons. You can use bold, sparingly. You can use italics, rarely. Just... never use underlines. Underlining basically only exists now to confuse people into thinking something is a link that they can click on.
The same goes for colors and fonts. Pick one, or maybe two. For the entirety of your document or presentation. (Yes, including any charts and graphs.) You can use shades of one of the colors, if you absolutely have to. But you don't! Do less. Be intentional about where you're applying any formatting, for any reason.
And finally: Don't use more than one of your formatting tools! Bold means something is important. Italics means something is emphasized. Color means something is distinct. Something that is bold, italicized, underlined, and brightly colored means you don't know what's important or what message you're trying to get across — it only communicates distraction. And it's hard to read.
Oh, and don't put borders on anything. If you can, remove and minimize the default borders that your tools put on things. "But then how will I separate stuff?!", you ask? This brings us to our next section...
You know how all your designer friends are always talking about white space? You basically can't have too much of it. Almost every time you want something to stand out, one of the best ways to do that is not through lots of formatting, but through a smart use of white space. Done properly, the point you're making will stand out on its own. Maybe you can just use a bit of minimal formatting to make it really pop, but it shouldn't take much.
A related technique is to spray them with bullets. Bullet points are a super powerful way to make content more skimmable for an audience, and perform a useful forcing function in making you edit your points down to be concise and roughly consistent. One less-obvious benefit of using bullet points is that it can often reveal to you as an author whether the information that you're providing is all in the same category. In prose, it can be easy to sometimes drift off-topic into unrelated topics, but with bullets, if you've got a list that has items which are very evidently out of place, it can be more evident.
Conversely, only use images and illustrations with purpose. Clip art almost never adds value. The same stock photos that came with your template are also meaningless. It is far better to have white space on the screen for your audience than to fill up that space with a graphic that has no meaning, especially if it's not specific to your context or message. Visual noise has a huge cost in its impact on people being able to absorb and understand your message, and it's extraordinary how common it is for people to have a slide that is 1/3 really carefully-crafted points that took a long time to devise and 2/3 an image that has zero purpose and was added at the last minute. Don't undermine your work with an unnecessary compulsion to fill up space just because a template suggests that you should.
You should master the formatting tools (especially in written documents and slideshow presentations) that let you control spacing and margins around your content. You can assign consistent styles (like headers in a document) to always have a lot of breathing room at the top, and then just consistently apply that style across your document.
A really common anti-pattern that I often see is needless inconsistencies. For example, people will vary the size, color or emphasis of titles across different slides in a presentation. Sometimes, this is an artifact of their creation — slides with this font came from this team that was working together, but slides with this other font were copied from some older presentation. But to the audience, the immediate message that they'll take away from a difference in formatting on the title of a slide is, "There must be a reason this changed, let me understand its significance." Suddenly, your audience is trying to deduce the semantic meaning of a change that you didn't even make on purpose.
The reason we start by saying to stop formatting everything to death is that this then makes it much easier to catch the inevitable inconsistencies and errors in formatting that will arise when you tell a complex story. Audiences are sophisticated, and used to seeing highly-produced media, and are very skilled at the innate human habit of identifying changes in pattern and shape. So they will assume that any change in formatting over the course of a document has some purpose and intent behind it. If you don't anticipate this reality, you end up with the worst of both worlds — you've captured their attention with something that's not relevant, and emphasized your own lack of preparation.
Learning your tools and using them well will make it easier to hide the seams between the different people and processes that created the work that you're sharing. And sweat the details here — if you're bringing over assets (like images, charts or embedded content) from other sources, make sure to use your tools to do another formatting pass and make it consistent with the rest of your document.
Just as many documents begin by exposing the insecurities of their authors, many times the order of information in a document reveals the relative difficulty of creating different kinds of content, rather than its actual importance. But people assume the first thing in a list is the most important! And they're being rational when they do so!
Especially in a world when some of the people attending your event, or participating in your meeting, will not have had time to review the whole thing in advance, assume that you have to front-load your key points at the beginning of the document. And within a particular page or slide, assume that you have to put the most pertinent info at the top, with supporting points below. If you're not ordering things by importance (because you want to set up a chronological flow, or because you're organizing by some historical categorization you've inherited) make that explicit in the text that your audience sees. Otherwise half your audience will be lost right at the top, wondering in their minds why these items are in an inexplicable order.
Similar to the importance of sequencing and order, you almost always want to start by clearly and simply stating your conclusion, or declaring your request or question. Very often, people feel a lot of anxiety about the need to preface their big dramatic point with lots of build-up. But you almost never want to be building dramatic tension in a professional context; this isn't a thriller where you're trying to surprise them with twists and turns.
It's perfectly fine to open with a key question or conclusion, step back to walk through the logic and context that leads to that point, and then restate at the end to drive towards your goal. But more often than not, if you don't set the stakes and make your point clear up top, you'll exhaust your audience, or leave them distracted trying to guess where you're headed all along the way.
Similarly, put the important points on the page! It's absolutely astounding how often people will take the most important conclusion about their work, or the most vital bit of context needed to make a decision, and assume they'll speak to it alongside the presentation of the document or slides. This is a surefire way to ensure that one of your most important stakeholders will be absent or distracted, and completely miss your point, and then go back and look at your document and not see that key fact you were trying to share. Even in many cases when people do include the key point, it's very often buried in some obscure place like the speakers' notes on a slide, or in an appendix that doesn't seem like a central part of the document. Don't demote your central statement to an ancillary channel.
People want to know where they're at in the story. This doesn't have to be fancy, you don't need a full timeline bar like a YouTube video. But a quick outline of progress (and, if you've got a particularly long document, recapping your position in that outline as you go) can help ensure people that they understand their place in the overall conversation.
This is one of those rare places where you may well want to use color. If you've got multiple distinct sections of a document or presentation, assign colors to them (keep your palette limited!) and use them utterly consistently so people know where they are, and that'll help build confidence that your audience knows how far along they are in the story.
Similarly, summarize any data that you present. You can trust people to be smart and to dig into numbers or charts, but start them off on the right foot with a little bit of "here's what these data show" right in the title of your chart or figure or data table, so they're mentally in the right place to absorb the more dense or inaccessible information.
An absolutely vital requirement, especially for documents or presentations that are driving towards a particular goal: Ask questions that are answerable. This sounds like an absurd contraint, but the actual absurdity is how often you'll see a giant headline on a slide that asks something like, "How can we do better?" That's a philosophical debate, not a prompt for an organization to make a choice!
One thing I've learned from being a parent is that constraining choice is a great way to get unstuck; unsurprisingly, the same tactic that works on 3-year-olds is very effective in board meetings. Rather than "what do you want for dinner?" (Inevitable answer, "I don't know, what do you want?") you can ask someone "Do you want spaghetti or chicken nuggets?" and even a 3-year-old will suddenly have a much more constructive answer.
Similarly, you'll want to constrain your requests to your audience to be something they can react to constructively. "Do we want to invest at the higher cost of Option A to move faster, or go with the lower cost of Option B to be more cautious?" That's an answerable question! And it's perfectly fine if it leads to a conversation where a third option is explored — but you never would have gotten there with a prompt that says, "What do we want to do next?"
You can never go wrong by restating first principles in the closing of your message. Remind people about alignment on purpose, and ideally alignment on values. This sets up for a constructive conversation, and clarifies the priorities that you all share in having a dialogue in the first place. You'll never go wrong thanking your audience or reminding them about past collaborative successes, either.
If your goal is to persuade, this gives your audience psychological permission to believe that you have their best interests in mind, too. If your goal is to make a tough decision, this gives them courage to go forward knowing that you'll be alongside them in their choice. If your goal is to inform, they'll feel more comfortable asking clarifying questions when you remind them that you're sincere in wanting to share your story.
That's it! Good luck making better documents, and just pretend that the underline button in your apps doesn't even exist anymore.
(Thanks to Waldo Jaquith for the reminder to add this one!)
One of the most important types of information you can share in a document is the title of the document itself. But so often, names are either just default generated titles, or reflect a lack of thought about context for the file.
Like we said to start, you need to start by thinking about the context of your intended audience. What are the words they'll use to search their email to find the file in the future. For example, you don't want to lead with the name (or the company/organization name) of your intended audience most of the time! If you're talking to someone at another company or organization, they'll try to retrieve a document by searching for the name of you or your organization, so include that in the title. If you're all on the same team, include the context of the project or initiative you're working on, and the specific goal you're working toward.
Similarly, you'll want to briefly include the date and a summary of the topic being covered in the document. This advice even extends to meeting invitations — inviting Sam to a meeting called "Meeting with Sam" is only going to create a useless or confusing entry on their calendar. Think through how they'll be referring to the conversation, and name the meeting after that context. Then name the document after the purpose of the meeting.
Finally, for versioning, sequential numbers are almost never sufficient on their own. (And needless to say, appending _final_final
to a document is... not going to produce the results you'd hope for.) Pick a naming convention that includes some kind of version context like dates right in the name, and it'll be much easier for your audience to know if they've got the most recent version.
But let's start by taking a look at the actual performance that Prince delivered, before diving into some of the drama of the story around it. It's a beautiful, searing performance of one of my favorite of Prince's 90s songs, Dolphin — and part of why I hold it in that esteem is because of how much I loved this particular performance. Dolphin is an eccentric pop-rock single about reincarnating as a Dolphin, covering a lot of themes of alienation that were increasingly at the fore of Prince's work at this era. Prince had just changed his name to an unpronounceable symbol the year before (you'll see Dave mocking that in the intro) as part of his reckoning with ownership and control over his work, had begun writing the word "slave" on his face, and had taken to saying "Prince is dead" as part of emphasizing the seriousness of his name change.
This is obviously the emotional context of choosing to perform a song about reincarnation, and the professional and cultural context of saying that "The Gold Experience", the album that contains Dolphin, would "never" be released. ("Never" was about a year later.) This was the beginning of the most active and confrontational part of Prince's battle against his record label, and he'd prepared well for the moment. Ahead of the Letterman taping, he had marshaled those of us who were his fans online. (In those days, Prince coordinated through the weekly fan group chats on AOL, which had a 90s-era equivalent feel to something like a private Discord chat for members of a Patreon now.) He told fans about the upcoming taping, and asked them to gather outside the Ed Sullivan Theater to protest against Warner Brothers holding the "Gold Experience" albumi hostage. We even got a flyer that we were supposed to print out and bring with us. I couldn't make it to the theater in time, but heard breathless accounts from those who were there of a few dozen fans having gathered, though everyone agreed it had not been as impactful a demonstration as they'd hoped it might be.
Within Prince's most engaged fandom, where some of these new songs like Dolphin had been feverishly traded amongst fans, this felt like a huge moment to stick it to the man. It also helped that Prince had been back on the charts just a few months earlier with one of his biggest hits ever — The Most Beautiful Girl in the World — and had managed to do that on an entirely independent release. This was the "Taylor's Version" moment that wouldn't see its mainstream moment with a fandom for another three decades. And then Prince showed up with a killer band and a strong song, and... well, we loved it. But Dave clearly thought it was weird.
Honestly, I still think the performance holds up incredibly well. But from Prince's standpoint, things got off to a rough start. Prince gamely plays along with an opening gag alongside Paul Shaffer, but pretty much from the start of the show, Dave keeps making fun of Prince's symbol name — including directly before the performance starts. At that point in his life, Prince took the symbol very seriously, and had seen it as part of his spirtual evolution. And interestingly, Dave's humor very much mirrors the way that Prince's sense of humor worked, especially in his personal life, in that it could be incredibly pointed and even mean-spirited. In Dave's case, that left him mocking the idea that the album being promoted would never be released, an issue important enough to Prince that he had organized a protest outside the studio at the time.
This led to Prince's last-minute decision to end his performance with a sort of staged death, with Prince making a "gun to his head" gesture followed by his dancer (and later first wife) Mayte Garcia wiping some fake blood on his face as keyboard player and musical director Morris Hayes played a gunshot sound. Prince's bodyguard then dragged the apparently-gone artist off the stage, leaving Dave to fill in for the usual pleasantries that followed a performance. Part of Prince's desire was likely in no small part due to his frequent distaste for handshakes, which would have been even more pronounced in an environment like the Late Show.
Shaffer offers a bit of a story about this in the clip recently shared on Letterman's channel, but also reveals just how much Prince was an enigma to even these late night legends who had hosted him.
What's clear to me is, Prince held Shaffer in some esteem, and most likely for nothing other than the simple reason that he knew the man could play. That was often the dividing line of how Prince would evaluate people who weren't in his direct orbit, and Prince was no doubt aware that Shaffer and his band would often go to commercial playing one of Prince's songs.
But it's equally clear that being mocked about issues as important to him as his identity or his control of his musical output weren't the kind of things that Prince was likely to have had a lot of patience for, even though he was undoubtedly well-acquainted with Letterman's general demeanor on the show. Prince also had to be aware that merely guesting on a late night show representing something of a come down from the most exalted commercial peaks of his career a decade earleir.
Whatever his feelings on the day, Prince clearly didn't hold that 1994 performance against Dave or the show; he returned just two years later with one of my favorite-ever TV performances that he did, a shimmering rendition of "Dinner With Dolores". This was not a successful single, but the musicality and charm of the performance has always stuck with me, and a particular highlight is that he ends his song by proclaiming "Free TLC!" (a reference to TLC having been exploited by the record industry) and then turning his perfectly-tailored coattails and stalking away.
This then brings us to one of the weirder parts of the anecdote that Shaffer shares, about Prince's affinity for Jay Leno. For many years, this was a trait that I often said was one of the worst things about Prince. The truth is, Leno was likely just far more deferential and Prince appreciated the accommodation enough to do a number of (not very funny, but they were probably having fun) skits and pranks with Jay, along with a number of great performances on his show.
But as noted, in one of Prince's first appearances on The Tonight Show, he held up a sign mentioning Paul Shaffer during the closing credits in a way that was clearly meant to throw some kind of half-joking shade at Dave. It's hard to discern exactly what point he was trying to make, except to clearly indicate to Dave that Prince had had some kind of musician-to-musician connection to Shaffer, and that Prince wasn't above a stunt to demonstrate that fact. There's a lot more to the Prince-and-Leno narrative, but it's told well in this interview with Bill Maher. Of course, neither Leno's nor Maher's reputations have aged very well, but it's revealing how much they wanted his recognition. (Maher, for example, had an entire bit about a "get over yourself" award during the first season of his show Politically Incorrect, with the award itself being a trophy in the shape of Prince's symbol. For a guy who pretended to mock Prince on air, it's telling that nowadays Maher sees a nod from Prince as the biggest sign of validation that his work even existed.)
If I had to guess, Prince probably threw shade at Letterman a bit and poked at the Dave-vs-Jay rivalry because he knew exactly how much these kinds of media outlets would want to win back his good favor, or to maintain their in with him. He was also likely grateful for the platform at a critical time in his career, and for having a place to show off both his work and his larger mission. In particular, since this entire episode happened only a year after Dave's headline-making departure from NBC, I think Prince likely assumed Dave would have had more empathy and appreciation for another creator fighting for respect and to have their work taken seriously. It is at least a happy ending that Dave owns his work enough to be able to put up clips on his own to comment about them, just as Prince's estate does, finally, own all the master recordings that he was fighting for in the battle that brought him to that stage at the Ed Sullivan Theater in the first place. These two men had successfully pointed their unique forms of obnoxiousness at battles which would cement their legacies.
And in the end, Prince gave the most access, and the most incredible performances of all his late night appearances, to Arsenio.
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