Celebrities Who Might Have Been Interesting Once, But Are Now Tiresome
Elton John
Nicholas Cage
Bette Midler
Bono
Mel Gibson
Kanye West

Debatable Whether They Were Ever Interesting, But Definitely Tiresome
Russell Crowe
Diddy
Ben Affleck

Dangerously Close to Tiresome
Michael Stipe
Gwen Stefani

(This project started as a piece of paper I left by the phone with the part about Once Interesting Now Tiresome and Elton John on it. Without even discussing it, Bob added Nicholas Cage to the sheet. He gets me. This is as far as we got.)