Last week on Late Show, Letterman estimated that there have been 105,000 guests on the different iterations of his talk shows. (During the CBS primetime special earlier in the week, Ray Romano mentioned the host had actually interviewed something closer to 18,000 folks; Dave is apparently determined to crack wise until the very end.) That's a lot of chitchat, but not all those guests are created equal. Below is a list of the 10 guests whose appearance on the show always filled us with the most excitement and anticipation. Note: This doesn't mean that these 10 were the most frequent guests — but when they were going to show up on Late Night or Late Show, we made sure to tune in.
Multiple sclerosis has kept Teri Garr out of the spotlight for the last decade, but she was an underrated staple of Late Night, serving as a funny, flirty sparring partner to Dave. Their most memorable moment came in 1985 when Letterman coaxed her into taking a shower during the show. (She finally relented, but only after announcing, "I hate you!") Their banter displayed a palpable sexual chemistry, but in the 1990s they had a falling out after Dave was irked that she spoke to TV journalist Bill Carter for his late-night wars book The Late Shift. But they eventually buried the hatchet, and Garr came on the Late Show in 2008 after suffering from a brain aneurysm. After Dave helped her to the couch, the host slyly joked, "I enjoyed the opportunity to grab you inappropriately."
The knock on Williams was that his inspired, high-energy talk-show segments started to become a crutch, merely an endless string of non-sequitur impersonations and undisciplined manic riffing. But especially since his suicide in 2014, it's impossible not to view those appearances with far more sympathy, recognizing the self-loathing and sadness that fueled his nonstop motion. When Letterman returned to Late Show after heart surgery in 2000, Williams was his first guest, coming out dressed in scrubs and surgical mask. ("Aren't you glad you didn't see this at the surgery?" Williams joked to the host. "'Hey, Dave! It's me!!'") Dave and Robin had known each other for 38 years when Williams died, first meeting at the Comedy Store in Los Angeles. "It's like nothing we had ever seen before, nothing we had ever imagined before," Letterman would say after Williams' passing about those early days of watching Robin's stand-up sets. "We didn't approach him because we were afraid of him, honest to god. You thought, 'Holy crap, there goes my chance at show business.'"
Before he was unofficially christened America's Most Beloved Movie Star, Tom Hanks could be a real smart-ass, which is abundantly clear from his appearances on Late Night. When he was on to promote Splash, he declared he didn't want to show the clip he brought because he was sick of seeing them. Right before Dave jumped to CBS, Hanks ribbed him about taking over the hallowed Ed Sullivan Theater. ("Why you'd want to move to 8 o’clock on Sundays is beyond me … [You're gonna] stand in front of a curtain and say, 'Now, have you seen plate-spinning like this?'") But as his stature rose, Hanks never lost his silly side when he'd come on Late Show, even in 2013 when he announced during the broadcast that he had Type 2 diabetes.
By Dave's count, Regis has been his most frequent guest, appearing 136 times. Viewers knew what to expect when Philbin would come on: Dave would harass him, Regis would get defensive and yell right back, and then maybe he'd would tell Joey Bishop stories. It was old-school talk-show shtick, but the affection beneath the animosity was apparent and endearing. And it was a sign of how much Letterman relied on Philbin that he had him on for that first somber Late Show after 9/11: "Thank God, Regis is here, so we have something to make fun of," he told the crowd.
Letterman has said he had no involvement in the hiring of Stephen Colbert as his replacement, but what the current and future Late Show hosts have in common is an abiding love for actress/author Amy Sedaris. A frequent presence on Dave's CBS show, Sedaris is one of the few female comics to really click with Letterman, who has always had an easier time getting chummy with male guests. A sarcastic wit, Sedaris managed to get Dave to open up about his son and his pets. As Letterman told his audience in 2005, "Now what you have to understand about this lovely woman — in addition to being a fine actress and a wonderful comedic talent, she's peculiar. … [She's] joyfully different than everybody else walking around on the planet. That's what makes her special."
When Julia Roberts first came on Late Night, she was 22 and had just appeared in Mystic Pizza and was promoting Steel Magnolias. During the interview, she kept being harassed by a bubble-eating dog, and Daryl Hannah showed up impromptu. It would be the last time Roberts would be upstaged on Dave’s show. The host's greatest flirting partner, Roberts recognized the chemistry she had with Letterman, milking their rapport over a series of memorable encounters that doubled as an unrequited love affair. "I love the woman in a way you can on television," Letterman told his audience during a 2001 broadcast. And when Dave married his longtime girlfriend Regina Lasko in 2009, Roberts coyly informed him, "I don't know if I can look you in the eye anymore … Last time I saw you, you were single and then I, like, hypnotized you in my white suit or something and you went off and married Regina."
No wonder David Letterman and Howard Stern saw each other as kindred spirits. Both proudly idiosyncratic, both refusing to kowtow to corporate bosses, they were two peas in a grouchy pod. What made Stern's appearances great in the Late Night days was that his button-pushing provocations helped give Dave's show its edge. (In 1984, Stern wondered how Vice President George H.W. Bush could get aroused being married to the much-older-looking Barbara Bush.) Few stars stood up for Letterman as defiantly as Stern did during the late-night wars, and even though the two men had a falling out later, they renewed their friendship before Dave's retirement. Those final Late Show appearances allowed viewers to enjoy some in-depth interviews and be reminded how good both men were in drawing out their guests through interesting, engaged conversation.
On Martin's final appearance on Late Show last week, Letterman told the writer-actor, "I think you and I are strange in the same way." It's easy to see why: Both men love absurdist humor, abhor Hollywood phoniness and wield a withering wit. (Also, Johnny Carson adored them both, having Martin guest-host The Tonight Show.) Watching Martin's appearances on Late Night and Late Show over the years was to see the comic evolve from budding movie star to Renaissance man, from jokester to refined satirist. Whether devoting a whole segment in 1987 to teaching Dave how to avoid card cheats or producing the classic 1998 clip "Dave and Steve's Gay Vacation," Martin always took his appearances seriously, which guaranteed they'd be hilarious.
Murray's legacy in Dave’s career is well established. He was the first guest on Dave's short-lived daytime show, the very first guest on Late Night and the first guest on Late Show. But the connection runs deeper than that. That surly reserve, that willingness to do the weird thing for a laugh: It's embedded in both men's DNA. For a couple generations of aspiring comics and procrastinating college students, Murray and Letterman's exchanges were like the meeting of too great smart-ass minds. Introducing Murray onto the show in 2013, Dave declared, "For my money, every film would be better if Bill was in it." And then, apropos of nothing (well, maybe that Soderbergh film Behind the Candelabra), Murray came onto the stage dressed like Liberace. "My heart has now taken flight," Letterman told him, clearly tickled. Ours too, Dave.
Lots of guys have featured comedic bits when they've come on Dave's show — Steve Martin, Will Ferrell, Bill Murray — but nobody so relentlessly brought his A-game as Bruce Willis. Dressing in a Snuggie; trying to do some David Blaine-esque live magic; hawking his new coffee brand, StarBruce; doing an interview while wearing a Sarah Palin wig; participating in a Top 10 list, "Top 10 Ways Bruce Willis Is Spending His Summer"; proving to be the most action-packed Late Show intern ever: No modern star was more willing to make a fool of himself in late night for the sake of a few goofy laughs. In Willis's recent years, his movies have arguably grown progressively lamer. But that didn't matter: We were just happy he kept making them so that he'd have an excuse to go back on Letterman again. When Dave retires, will Bruce, too?