Here’s What Millennials Should Know About David Letterman And His Real Legacy

If you’re under the age of, say, 30, many of you may be viewing last night’s retirement of David Letterman the way the previous generation viewed the retirement of Johnny Carson. We understood that Carson was revolutionary; we understood what he meant to the late-night landscape, but it was more difficult to understand why he was so beloved. From our perspective, Carson was a very amiable often very funny guy, but his show was very traditional: Monologue, bit at his desk, guest, guest, stand-up act/musician. When Carson retired, his format seemed staid because of Letterman. He had taken Carson’s framework and subverted it, flipped it, poked it, shook it around, and spit out something refreshing and new and exciting.

If you’re someone who grew up on The Daily Show or The Colbert Report or Conan, you might also wonder what the big deal about Dave is. If all you really know of Dave is the last 22 years on The Late Show, I don’t blame you, because Late Show Dave is a very different animal than Late Night Dave. Late Show Dave has had Regis Philbin on 150 times, and while Late Night Dave liked and respected Regis, he wasn’t the kind of guest that Dave was going to have on every other night.

Late Show Dave was more palatable, more friendly, less sarcastic, and more traditional. Late Night Dave was a snarky wiseacre, which is a euphemistic way of saying that Late Night Dave was a prick. I say with the deepest admiration, but there’s a reason that Cher was afraid to go on on Dave’s show, and a reason that Cher thought Dave was an “asshole.” Because he was, and that’s what we loved about him.

Late Night Dave gave zero f*cks. He was punk rock. He was anti-establishment. In fact, he bad-mouthed his bosses so much that it was ultimately part of what cost him his Tonight Show gig (more on that in a moment). He hated show business. Yet, it was his job to interview those in show business. If he didn’t like a guest, though, you knew it immediately. He didn’t pretend to like your movie. He kissed no one’s ass. He’d harass and heckle and mock some of his guests, and he’d give the audience at home a look that said, “Who is this dweeb?” At 12:30, he also didn’t get the caliber of guests he gets on The Late Show. Instead, he’d bring on these strange people, like a guy who’d been struck by lightning, or a guy who flew 15,000 feet in the air on a lawn chair (and was nearly killed by a Delta airplane), and he’d often just screw with them. In fact, he screwed with a lot of people; he asked the questions that we at home wanted to know the answers to, but that other hosts wouldn’t dare to ask.

And while that era of Dave is best known now for things like Stupid Pet Tricks and Small Town News (which Leno basically reappropriated as “Headlines”), there was a lot of off-the-wall weird stuff going on, too. Like Chris Elliott taste testing dog food; or Larry “Bud” Melman, who was just a very strange old guy who did unexplainably bizarre things; or he’d bring out the Late Night Thrill cam. He did Viewer Mail on Fridays (because that’s when we all stayed up to watch it live), and during that segment, everything was unexpected. One time, he got a letter from a woman who was “concerned about his image,” so he went to that woman’s house, met her family, snooped around in her room, and then tracked her down at her place of employment, gave her a hard time, and then asked her out to lunch. That was vintage Dave.

Late Night Dave was another guy. He gesticulated wildly. He was anxious, and depressed, and acerbic, and sometimes mean-spirited, and he was different than anything else on, and I don’t mean that in the way that Kimmel is different from Fallon. He was wildly different, and there was nowhere else on television you could get that fix except for Dave.

He was also a recovering alcoholic (did you know that Bill Murray and half of Dave’s writing staff was plastered during Murray’s first appearance?). Late Night Dave had a bone to pick. He had a chip on his shoulder borne out of insecurity. He was an asshole, but he was our asshole. He was on our side, calling out the weasels, boobs and dickheads in entertainment.

Late Night Dave was on at 12:30 before DVRs and before YouTube. You didn’t watch clips of Late Night the next morning. You either stayed up until 1:30 on a school night to see Dave, or you recorded it on your VCR and watched it the next night. You didn’t casually watch Letterman. You either hated him (and a lot of people didn’t care for him at the time) or you were a passionate, hardcore fan. He was divisive.

We still love Late Show Dave, of course. But more in a way that we love our Dads. He’s Grandpa Dave now. He’s a little cranky sometimes, and he still gets a little weird on occasion. He’s revered, and respected, and beloved, but Late Show Dave is not the guy who inspired Jimmy Kimmel or Conan O’Brien. He’s not the guy who changed the late-night landscape (although, it’s all beginning to revert to Carson-era late night now). It was Late Night Dave that inspired us, that made us feel alive at 1:00 in the morning, because we were experiencing the thrill of seeing something new and different and exhilarating. Late Night Dave reinvited late-night. He was The Sopranos of his time.

So, as you watch the post-mortems on last night’s goodbyes to Late Show Dave, just know that there was a lot more to him than a guy who flirted with Julia Roberts, or came up with the Top 10 Lists (which he’d actually given up at one point for a while because it’d gotten too ‘”establishment”), or who came back from a heart surgery. Letterman is an institution now, but there was a 11-year period in his career when he raged and rejected that institution. And no matter what you might think of this David Letterman, I promise you would’ve have loved the old Letterman. Or hated him. But there was no, “I could take him or leave him” in-between.

And if you really want to know why Dave didn’t get The Tonight Show, it wasn’t entirely Leno’s fault. He was just an available alternative. The real reason Dave didn’t get the gig is because of shows like this, in which he mercilessly mocked his new bosses at G.E. on the very day NBC was taken over. It’s basically a 13-minute takedown of the people who would write his checks for the next eight years. You’ll never see anything like this on television again, and no one — except occasionally John Oliver — comes even close.