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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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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?

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