Thirty-three years, two major networks, one prodigious, iconic dental gap.
The late-night legend’s last show airs tonight, after which Stephen Colbert will take over.
Let’s use this as an excuse to, yes, sob, and then look back on his best moments of Late Night and the Late Show.
10. Dave returns from heart surgery (2000)
A little more than a month after Letterman underwent quintuple-bypass surgery on his heart, he returned to riotous applause and the opening line: “Wait ’til you hear what happened to me.” Shortly thereafter, Jerry Seinfeld came onto the set and morbidly remarked, “What are you doing here? I thought you were dead!”
9. Drew Barrymore flashes Dave (1995)
The same year that she posed nude for Playboy, the ’90s teen rebel du jour discussed performing in the buff at a New York burlesque club. When Letterman expressed incredulity, she climbed up on his desk to writhe around and flash her boobs. The best part isn’t Barrymore’s dance itself, but the bug-eyed look of surprise on Letterman’s face.
8. Warren Zevon’s farewell (2002)
The “Werewolves of London” singer had been a fixture on Letterman’s shows since the very beginning, occasionally even filling in for Paul Shaffer as bandleader. Shortly after Zevon was diagnosed with terminal lung cancer, the host devoted an entire show to his friend. “I might have made a tactical error by not going to a physician for 20 years,” Zevon joked. He rounded out the night with what would end up being his final public performance, and died less than a year later.
7. Dave interrupts The Today Show (1985)
Decades down the road, it’s easy to forget how irreverent Letterman was in his early days on TV. Via a bullhorn from a window of the RCA Building, he disrupted an outdoor taping of The Today Show, shouting: “I’m Lawrence Grossman, the president of NBC News! This primetime program was my idea, and I’m not wearing pants!” Bryant Gumbel held a grudge about the incident for years afterwards.
6. Dave confesses to having affairs (2009)
How do you handle being outed as a womanizer? If you’re Letterman, you tell a long, rambling story about being blackmailed, peppered with plenty of jokes to soften audience opinion, before finally getting to the heart of the matter: “The creepy stuff was that I have had sex with women who work for me on this show.” Not the man’s finest hour—but at least he fessed up, we guess.
5. Bill Murray is the show’s first guest (1982)
You couldn’t ask for a more awesome interview to inaugurate a talk show than this guy. A year after Stripes, a very game Murray broke in the guest’s chair by calling for a standing ovation for the new host. Of course, he laid into him briefly thereafter: “I swear, Letterman, if it’s the last thing I’m gonna do, I’m gonna make every second of your life from this moment on a living hell.” Murray finished off with an all-singing, all-dancing cover of Olivia Newton-John’s “Physical” that remains a wonder to behold.
4. Dave responds to the 9/11 attacks (2001)
The Late Show returned to the air less than a week after New York City was still reeling from the tragedy. To open the show, a choked-up Letterman delivered a moving monologue to his longtime home city, praising New Yorkers, and Mayor Giuliani in particular, for their courage. He expressed the country’s inexpressible sadness when he said of the terrorists’ motives: “If you live to be a thousand years old, will that make any sense to you? Will that make any goddamn sense?”
3. Crispin Glover acts like a maniac (1987)
The jury is still out on whether the eccentric actor’s infamously crazed appearance was a piece of performance art or a genuine freak-out. But bizarre it certainly was: Glover showed up in towering platform boots and what seemed to be a bad wig, talking at a panicked pitch. After Letterman refused his challenge to arm wrestle, Glover declared, “I can kick!” and came within inches of clocking the host in the face. He never even got to show off the weird objects in a glass case he brought along—which were, as it turned out, wax replicas of diseased eyeballs.
2. Madonna doesn’t play along (1994)
After Letterman’s casually sexist intro, in which he says that she’s “slept with some of the biggest names in the entertainment industry” and asks her to kiss a random dude in the audience, the guy kind of had it coming. And by it, we mean Madge unleashing a highly censored interview in which she calls Letterman a “sick fuck,” refuses to answer most of his questions and turns everything into a dirty joke. But considering she appears after the commercial break smoking a cigar, we’re guessing Letterman couldn’t have been that put out.
1. Jerry Lawler slaps Andy Kaufman (1982)
The late comedian’s ongoing war with pro wrestler Lawler was later revealed to be an elaborately staged hoax. But when the pair showed up on Late Night a few months after their famous fight with Kaufman still wearing a neck brace, many people still thought it was the real thing. The two hurled insults at each other (“I couldn’t warm up to this guy if we were cremated together!”) before Lawler slapped Kaufman so hard he fell out of his chair. The comic retaliated by calling his adversary a “motherfucking asshole” and throwing coffee in his face. Letterman’s bemusement at the whole thing proved early on that he was just the man for this hosting gig.