David Letterman (whose team is doing a wonderful job of presenting and narrating his formidable archives) recently posted an amusing anecdote about Prince's first appearance on his show, in December of 1994. It's a fascinating story, because it reveals a lot about the two men who were so culturally influential in the 80s, and so transformative of their industries in the 90s. And also reminds us of what happens when two very talented, but totally insufferable and spoiled, grown men cross paths in an unexpected way.

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.