14 Most Memorable Guests in David Letterman History

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.

1. 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.

2. 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?

3. Drew on the Desk

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

4. 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.

5. 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.

6. 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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