30 most shocking late night scandals

19. Jimmy Kimmel impersonates late night rival Jay Leno

As we’ll see on this countdown, and like I already mentioned earlier, Jay Leno is one of the more controversial late night personalities. Even a majority of his peers seem to hold disdain for him. He may have been a leader in the late night ratings, but it still seems Jay just wasn’t a very popular person.

One fellow who hates Jay is Jimmy Kimmel, a late night rival. Kimmel straight up said “f-ck him” in reference to Leno in front of a crowd at one point. But later, he’d go the extra mile by spending an entire episode of Jimmy Kimmel Live mocking Jay.

For the opening monologue, Kimmel came out in full Jay Leno garb. This includes wearing a gray hair wig and a prosthetic chin. Kimmel goes all out with the voice too, using a comically exaggerated lisp and squeakiness to mimic talking as Jay. And Kimmel keeps it going for a bulk of the program.

Because this was happening in the midst of the NBC controversy, where Conan was getting bumped from The Tonight Show, this was worked into the sketch. Kimmel jokes that, as Jay Leno, he is there because he’s taking over all the late night shows.