8. JOHN MAYER

When: 2009
Comment: "I liked him before he started talking. I liked his singing, and then he ruined it with talking. It's just like if I started to sing, you got that douchebag?"

At the Women in Film Crystal and Lucy Awards, Handler took a shot a Mayer, whose ex Jennifer Aniston was in the audience. Mayer used his now non-existent Twitter to write, "I’m trying to figure out why Chelsea Handler has such seething hatred for me. I must remind her of someone she knows and doesn’t like."