Jay Leno has his man-on-street bits. Jimmy Fallon has his viral songs, and Jimmy Kimmel has his star-studded sketches. But David Letterman has always been, and still is, the best interviewer on late-night TV.
Last August, Letterman celebrated a two-decade reign as the genre’s king of the tongue-in-cheek cross-examination. Through the years, Letterman has shown an unflappable ability to crack through the most polished celebrity veneers, catching his guests off-guard with biting, provocative, and playful inquisition. The result: great TV.
In honor of the anniversary, here’s a tour through some of the most memorable interviews of Letterman’s career, both from his 20-year CBS tenure and before.
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Lindsay Lohan (2013)
Lindsay Lohan’s April 2013 interview with Letterman was labeled everything from “uncomfortable” and “incredibly awkward” to “epic.” The mixed reviews are understandable. Lohan proved admirably game considering the odd circumstances she was appearing under. Though she was there promoting her role in Scary Movie 5, she was also about to enter rehab … again. Letterman wasn’t lobbing softballs: “Aren’t you supposed to be in rehab now?” “Yes or no, do you steal stuff?” “Did Charlie Sheen loan you money?” Lohan somewhat gracefully handled it with squirms and giggles, chiding him: “We didn’t discuss this in the pre-interview, just saying.” By the end, Letterman was praising her for having “enough spine, enough poise, enough sense of yourself” to appear on the show … and Lohan was crying.
Joaquin Phoenix (2010)
“It’s been three years since you’ve been on the show and, I have to say, you look different than I remember.” Sporting a beard the cast of Duck Dynasty would be envy, wearing sunglasses, and chewing gum, Joaquin Phoenix refused to engage with Letterman in the slightest, which actually gave Letterman one of the most engaging interviews ever. The odd behavior has since been revealed to be performance art, but at the time the Culture-at-Large was collectively pacing back and forth, nervously fretting over what appeared to be a drug-fueled downward spiral. Still, in the (hairy) face of a precarious interview, Letterman was aces: “What can you tell us about your days with the Unabomber?”
Paris Hilton (2007)
Letterman’s 2007 interview with Paris Hilton accomplished the unthinkable: It made us feel sorry for Paris Hilton. The “film star, recording artist, entrepreneur”—as she was cheekily introduced—marched on stage thinking she was about to promote her new perfume alone, painfully unaware that she was strutting toward the slaughterhouse. Letterman gleefully ambushed the celebutante, feigning roughly 30 seconds of pleasantries before going in for the kill: “Good for you, how’d you like being in jail?” He then shot off rapid-fire questions about every detail about her incarceration—and laughed out loud at every answer—until, with bullet holes all over her ego, she was forced to plead for mercy and a new conversation topic. (He ignored her.) It was cruel. It was excruciating. It was brilliant—at once one of the most deplorable and impressive interviews Letterman’s ever pulled off.
Bill O’Reilly (2006)
Bill O’Reilly and David Letterman’s 2006 confrontation was the talk-show equivalent of a game of Rock ’Em Sock ’Em Robots, two guys taking antagonizing jabs at each other and waiting for his sparring partner to get so fed up that his head finally explodes. Their mutual disdain for each other drips right through the TV. Sure, Letterman had the goodwill of the room—he was on home turf, after all—but suffice to say that by the end of their 11 minutes together, it’s O’Reilly’s head that’s “socked” off first.
Dan Rather (2001)
It was not the craziest of interviews, but Letterman’s sit-down with Dan Rather on September 16, 2001, was under the craziest of circumstances. It was Letterman’s first Late Show to air after the 9/11 attacks. Rather cried. Twice. After the first time Rather got emotional, Letterman quickly cut to commercial. After both times, Rather apologized for crying, saying it was not professional. Letterman’s straight talk, a gift he is a legend for holding, was never more on point: “Yeah, you’re a professional, but good Christ, you’re a human being.”
Harmony Korine (1998)
Shock-and-awe filmmaker (Kids, Gummo, Spring Breakers) Harmony Korine’s shlubby, fidgety, and seemingly under-the-influence interview with Letterman in the ’90s was uncomfortable enough for a ban from the show in the future to be understandable. But the real reason Korine has not been invited back to the Late Show these past few decades was revealed only recently by Letterman, who said that he was found rummaging through Meryl Streep’s purse backstage: “And so I said: ‘That’s it, put her things back in her bag and then get out.”
Farrah Fawcett (1997)
It’s hardly frowned upon to throw back a drink or two to loosen up for a nerve-racking public appearance. Farrah Fawcett, however, appeared to have downed the whole bottle—and maybe not of booze—prior to a 1997 Late Show interview so loopy that gossip rags quickly speculated that she was on drugs. Here’s a sample exchange. Letterman: “You were kind of harried getting over here. Was there a problem, was there a traffic?” Fawcett: “There were people!”
Drew Barrymore (1995)
“Please welcome back the lovely and enchanting Drew Barrymore,” Letterman says as the actually naughty and wild actress skips on stage, peacocking her lower back tattoos for the camera. Her appearance happened to fall on Letterman’s birthday. Barrymore celebrates by proclaiming herself “Lolita” dancing provocatively on his desk, and then flashing him. The moment was a brutal wakeup call. The little girl from E.T. was old enough to flash her breasts. Happy Birthday, Dave. You probably never felt so old.
Madonna (1994)
“Aren’t you going to smell them?” Madonna asks. “I gave him my underpants and he won’t smell them.” Come for Madonna’s shocking one-liners. Stay for Madonna smoking a cigar and actually talking with an American accent. #neverforget
Harvey Pekar (1987)
Conventional wisdom says that people like, or at least can’t help, watching a trainwreck. That may be true, but it’s a whole other thing to route the train to a location and then orchestrate the wreck for entertainment. That was the lot of comic-book author Harvey Pekar, immortalized by Paul Giamatti in the 2003 film American Splendor, for years on Letterman’s program. While Letterman, his audience, and certainly the NBC brass delighted for a while in laughing at Pekar as he gradually loses his composure, eight increasingly cantankerous appearances and one bristling criticism of General Electric (which owned NBC) eventually got him banned from the show.
Crispin Glover (1987)
You know what’s always fun? When an actor does a talk-show appearance in camera and doesn’t warn anyone. By that measure, Crispin Glover’s appearance to promote his role in Rubin & Ed was a freaking blast.
Andy Kaufman (1982)
The calling card of a late-night talk show is supposed to be unpredictability and danger. If that’s true, then the Late Show With David Letterman reached its full potential in 1982 during a joint interview with wrestler Jerry Lawler and comedian/wannabe-wrestler Andy Kaufman. The two had been feuding. Lawler reaches his breaking point and slaps Kaufman, after which Letterman cuts to a commercial. Kaufman returns after the break to deliver an expletive-ridden tirade against Lawler. It was later revealed that Lawler and Kaufman’s sparring was staged. Letterman, however, was oblivious to this—which certainly seems to hold up based on his frazzled reaction in this clip.
