PLAYBOY: You excelled at it, especially back in 2010 when he abruptly repossessed The Tonight Show from Conan O’Brien after his nightly prime-time Jay Leno Show had failed. You even imitated him, with the help of prosthetics, for a full installment of your own show. No mercy there at all?
KIMMEL: I don’t know. I always feel bad if I hurt anybody’s feelings, but I don’t believe Jay Leno has actual feelings, and he doesn’t seem to be that worried about other people’s feelings. Anyway, I can do a pretty good Leno imitation. It was a lot of fun to be him—also much easier, particularly in constructing “his” monologue for that night. I have a filter mechanism in my head every night when I put together the monologue for our show: If I can imagine Jay Leno telling a joke, then I won’t do it, even if it’s a good joke. There are three ways he does a joke, every single time, always with the same rhythm. The difference between Leno’s jokes and Letterman’s jokes is like the difference between Celebrity Jeopardy! and regular Jeopardy! During Celebrity Jeopardy! anyone could get all the answers; there’s an accessibility that makes you feel like you’re smart. I think Leno’s jokes are similar in that way. Real Jeopardy! requires an attempt at greater mind function.
That’s an excellent way of putting it, don’t you think? I prefer Letterman to Leno in part because Dave forces me to pay attention. If I’m reading email and only half-listening, I might miss out on a crucial line that explains why he got another big laugh three jokes later.