After 30-plus years in the business of making everyone around him laugh, David Letterman is packing up his Late Show stage and going home to Connecticut.
Over his multiple decades in the spotlight, Letterman has interviewed actors, actresses, singers, politicians and everyone in between.
But certain guests and certain appearances stand out above the rest.
There was the time Demi Moore did push-ups on stage. Or Madonna kept dropping the F Bomb. Or Drew Barrymore flashed the host. Or Bill Murray simply acted like Bill Murray.
In honor of Letterman retiring on May 20, 2015, we’ve collected photos of the star’s 14 most memorable celebrity interview subjects.
They cross all industries and don’t have a lot in common on their own, except for one thing: they all got to enjoy the unparalleled experience of sitting across from David Letterman.
Demi Moore Pushes Up
ONE! TWO! THREE! FOUR! In order to promote G.I. Jane, Demi Moore dropped to the ground and did push-ups during an appearance with David Letterman in 1996.
What a Drag
Howard Stern, a frequent Late Show guest and close friend of the hose’t donned full drag and danced for Letterman in 2009 while promoting his book Miss America. Dave looks thrilled, doesn’t he?
Drew on the Desk
Most memorable talk show appearance ever? Drew Barrymore flashed Letterman in 1995 when she stopped by The Late Show.
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.
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.
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.
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.
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.
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.
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.
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.
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.”
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.
(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.