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.

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