Late Night with Conan O'Brien from like 97-2008 was the best late night show in history.
Max Weinberg, Joel, all the characters, all the writers, the recurring segments like Secrets, even the old stuff like PSAs. The Triumph segments at the Star Wars movies, etc. You just had to be there.
Conan was the Michaels to the extreme.
https://www.youtube.com/watch?v=4ZDU4hv7sFE 
