Yesterday, August 29, marked David Letterman’s 20th year hosting the Late Show on CBS. While fans are probably a little disappointed that Dave didn’t give in and do a retrospective episode or primetime special (Neither one was ever going to happen. This is Letterman we’re talking about.), there’s no reason we can’t, with the help of YouTube, take a look back at Dave’s time on CBS.

First Episode

Dave may not have gotten The Tonight Show and NBC may have tried to sue him for using their intellectual property, but that didn’t stop Dave from bringing Larry “Bud” Melman, now using his real name, Calvert DeForest, to CBS. In fact, DeForest was the first person seen on the Late Show. Unfortunately, the clip below doesn’t have DeForest’s appearance on the first show, but it does have Ed Sullivan introducing Dave.

David Letterman and Rupert Jee Annoy People

Passing the Late Night Torch

Despite being on competing networks, Dave has always had a tremendous about of respect for his Late Night replacement, Conan O’Brien. In Conan’s very first appearance on the Late Show, it’s clear that Conan hasn’t yet come into his own.

Drew Barrymore Flashes Dave (Full Interview)

Any late night fan has seen this clip a million times, but it’s still nice to see that Drew Barrymore has come a long way from flashing Dave.

Joaquin Phoenix

The Joaquin Phoenix interview is another moment from the Late Show that has been talked about to death, but is on this list for completion.

Stupid Pet Tricks

Of course, this list wouldn’t be complete without Madonna’s infamous interview where she asks Dave to smell her underwear.

What sketches and moments should be on this list? Let us know in the comments!