(Not) Live with Regis Philbin

(Not) Live with Regis Philbin

Regis Philbin has appeared as a Late Show guest more than any other celebrity guest. He's tight with the hilarious guest.
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A Kiss from a Pretty Woman

A Kiss from a Pretty Woman

Julia Roberts has always been very close to Letterman. And she got especially close to him during this appearance.
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It's Cher!

It's Cher!

After being repeatedly asked to appear on the talk show, Cher didn't make it until 1987. Once on stage, she notoriously referred the host as an "a--hole."
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A Very Special Guest

A Very Special Guest

Letterman dedicated an entire 2002 episode to his close friend, musician Zevon, after the latter was diagnosed with terminal cancer. He was one of the only people ever to be the sole guest on an episode of The Late Show.
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A Dirty Material Girl

A Dirty Material Girl

Madonna has visited Letterman numerous times over the years, but her longest-lasting legacy stems from the 1994 appearance when she dropped the F-bomb 14 times.
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Prime Letterman Material

Prime Letterman Material

Joaquin Phoenix stopped by in 2009. He wore a giant beard and sunglasses and remained mostly quiet and sullen, allowing Letterman to have tons of fun at his expense.
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A Chat with Borat

A Chat with Borat

In 2006, Letterman was caught off guard when Sacha Baron Cohen appeared in character as Borat. The subsequent interview was awkward... and awesome.
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An Awkward Night in Paris

An Awkward Night in Paris

In 2007, Paris Hilton appeared on The Late Show... and Letterman peppered the former sex tape star about her stint in jail. He later apologized for not letting the issue go.
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A Man and His Mentor

A Man and His Mentor

Letterman has never been shy about gushing over his mentor, Johnny Carson. The latter appeared opposite Letterman several times, including the legend's final TV appearance in 1994.
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Going Gaga for Gaga

Going Gaga for Gaga

In 2011, Lady Gaga was promoting her album Born This Way whenshe claimed she wore a mask because she was Batman. She then ripped up Letterman's notes and chewed them up.
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Bill Murray For all the Wins!

Bill Murray For all the Wins!

Bill Murray was Letterman's first-ever guest on his late-night show in the '80s, and also one of the comedian's first guests on the Late Show in 1993. He never fails to crack us up.
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Drew on the Desk

Drew on the Desk

Most memorable talk show appearance ever? Drew Barrymore flashed Letterman in 1995 when she stopped by The Late Show.
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David Letterman Biography

David Letterman Photograph
David Letterman hosts our favorite late-night talk show. His top 10 lists are always good for a laugh. In the summer of 2009, he got into... More »
Full Name
David Letterman