On the Late Show‘s first-ever episode, Monday, Aug. 30, 1993, Bill Murray helped Letterman mark his territory by spray-painting his desk with the word “DAVE.” Murray would go on to become a frequent guest – often pulling memorable stunts during his appearances.

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August 1993

Alan Singer/CBS

On night two of the show, Robin Williams did what he did best – make people (in this case, Letterman and the not-pictured audience) laugh.

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September 1993

Alan Singer/CBS

With N.Y.C. in the background, Letterman grinned from the seat at his new post. As he should have: That month alone, he welcomed Demi Moore, Bruce Willis, Al Gore, Sarah Jessica Parker and Rod Stewart to his stage.

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September 1995

Alan Singer/CBS

Along with the actors, actresses, models, politicians and comedians, there have been plenty of musical visitors to the Late Show, too. Here, David Bowie performs in the show’s early years.

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April 1995

Alan Singer/CBS

A young, wild and free Drew Barrymore gave Letterman quite a shock when she jumped on top of his desk, danced – and flashed him. His reaction said it all.

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November 1995

Alan Singer/CBS

Letterman cracked up while interviewing a 34-year-old George Clooney, then the hot new star of ER.

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July 1996

Alan Singer/CBS

Demi Moore sported her buzzed-about shaved head (for her role in the film G.I. Jane) during a trip to the Ed Sullivan Theater to talk up another of her controversial flicks, Striptease.

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November 1998

Alan Singer/CBS

A Late Show guest many times over, Steve Martin stood with Letterman on the show’s fifth anniversary.

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January 1999

Alan Singer/CBS

Italian actress Sophia Loren brought a little bit of home to the Ed Sullivan Theater in 1999, teaching Letterman how to make tiramisu on stage.

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September 2001

John P. Filo/CBS

Though generally light, the Late Show had its serious moments: Dan Rather, then-anchor of CBS Evening News, got choked up while discussing the Sept. 11 terrorist attacks.

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November 2002

John Paul Filo/CBS

On this particular episode, everyone in the audience was a resident of Schoharie, New York, and the town’s mayor read the nightly “Top 10” list. Nine years later, the village would pop up on Letterman’s radar again; he helped fundraise for families there who’d been hit hard by 2011’s Hurricane Irene.

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September 2003

John Paul Filo/CBS

Synonymous with both Letterman and the Late Show is the program’s set at the Ed Sullivan Theater in Midtown Manhattan. In 2003, the New York Philharmonic performed on the building’s roof.

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November 2005

John Paul Filo/CBS

In preparation for Oprah Winfrey’s first-ever Late Show visit, Letterman posed with a portrait of the two of them. At the 1995 Oscars, he made a dud of an “Oprah, Uma, Uma, Oprah” joke, “introducing” the talk show hostess to Thurman, so Winfrey’s 2005 appearance on his show was seen as a burying the hatchet of sorts (though she insisted there was never a feud).

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February 2009

John Paul Filo/CBS

Letterman’s hilariously awkward interview with Joaquin Phoenix went down as one of his weirdest. The nine-minute chat touched on Phoenix’s hip-hop aspirations and an injury to Letterman’s thumb, among other topics. It later came out that the whole thing was just promotion for Phoenix’s bizarre pseudo-documentary, I’m Still Here.

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July 2009

Jeffrey R Staab/CBS

Two icons in one shot: the Ed Sullivan Theater, home to both Letterman and the Late Show for more than 20 years, and Paul McCartney, who performed on the theater’s marquee. McCartney and his band The Beatles made their U.S. debut in 1964 on the theater’s hallowed stage.

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August 2009

Jeffrey R. Staab/CBS

He’s had many athletes on the show, but when New York Yankees first baseman Mark Teixeira stopped by, Letterman got in on the action himself. The two did a round of batting practice outside the theater on Broadway.

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December 2010

John Paul Filo/CBS

Smooches all around! Dustin Hoffman planted one on Robert De Niro’s head as they promoted their film Little Fockers together.

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September 2013

Jeffrey R. Staab/CBS

Letterman and Cher have had their tense moments (back in the ’80s, she called him an “asshole” on camera), but clearly, they came around on one another by 2013.

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April 2014

Jeffrey R. Staab/CBS

The past and the future came together as Letterman snapped a selfie with Stephen Colbert, who eventually replaced him as the host of the Late Show.