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Dave’s Faves: Top 10 Repeat Guests on Letterman

From flirty Julia Roberts to flighty Regis Philbin, these stars kept coming back for more

Julia Roberts

Julia Roberts on 'Late Show with David Letterman.'

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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.

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THE TONIGHT SHOW STARRING JOHNNY CARSON -- Pictured: (l-r) Actress Teri Garr, guest host David Letterman on December 5, 1979 -- (Photo by: Paul Drinkwater/NBC/NBCU Photo Bank via Getty Images)

10

Teri Garr

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."

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LATE NIGHT WITH DAVID LETTERMAN -- Episode 1404 -- Pictured: (l-r) Actor Robin Williams during an interview with host David Letterman on December 18, 1990 -- (Photo by: NBC/NBCU Photo Bank via Getty Images)

9

Robin Williams

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.'"

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LATE NIGHT WITH DAVID LETTERMAN -- Episode 1810 -- Pictured: (l-r) Actor Tom Hanks during an interview with host David Letterman on June 25, 1993 -- (Photo by: NBC/NBCU Photo Bank via Getty Images)

8

Tom Hanks

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.

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NEW YORK - NOVEMBER 17: Regis Philbin tells the Late Show audience that he was kissed on the lips by David Letterman when Letterman appeared earlier in the week on Philbin's show. Regis Philbin was Dave's guest on the Late Show with David Letterman on the CBS Television Network. (Photo by John P. Filo/CBS via Getty Images)

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7

Regis Philbin

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.

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NEW YORK - APRIL 15: Amy Sedaris gives Late Show host David Letterman a kiss during 4/15/15/t aping in New York (Photo by John Paul Filo/CBS via Getty Images)

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6

Amy Sedaris

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."

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NEW YORK - DECEMBER 12: Julia Roberts catches up with Dave on the Late Show with David Letterman Thursday Dec. 12, 2013 on the CBS Television Network. (Photo by Jeffrey R. Staab/CBS via Getty Images)

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5

Julia Roberts

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."

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NEW YORK - FEBRUARY 1: Howard Stern throws the money set aside by David Letterman to entice Brad Pitt to appear on the Late Show to the audience during the Wednesday 2/1/2012 taping of the Late Show with David Letterman on the CBS Television Network. (Photo by John P. Filo/CBS via Getty Images)

4

Howard Stern

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.

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NEW YORK - DECEMBER 22: Actor Steve Martin, left, feigns sleep after asking CBS LATE Show host David Letterman to tell him about his new baby on the Late Show with David Letterman, December 22, 2003 on the CBS Television Network. This photo is provided by CBS from the Late Show with David Letterman photo archive. (Photo by John Paul Filo/CBS via Getty Images)

3

Steve Martin

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.

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NEW YORK - AUGUST 30: Bill Murray spray paints Dave's desk on the first taping of the Late Show with David Letterman, August 30, 1993 on the CBS Television Network. This photo is provided by CBS from the Late Show with David Letterman photo archive. (Photo by Alan Singer/CBS via Getty Images)

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2

Bill Murray

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.

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NEW YORK - JULY 15: Actor Bruce Willis shares a laugh with Dave Lettermanon the Late Show with David Letterman Monday July 15, 2013 on the CBS Television Network. (Photo by Jeffrey R. Staab/CBS via Getty Images)

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1

Bruce Willis

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?