TVSquad

Appearing on the Late Show with David Letterman is a big deal for most comics. For Brian Kiley, who appears on the show tonight, it's a little strange. Kiley is a writer for Conan O'Brien (both for Late Night and the new Tonight Show), and starting June 1, his boss will be Letterman's direct competitor.

Kiley has done the Letterman three times before, he notes as an emergency replacement for another act that dropped out. And while he says he would never have gone on the Late Late Show with Craig Ferguson, since that show is in the same time slot as Late Night, O'Brien and Letterman have always had a cordial relationship, and no one ever said anything before. That might change now.

"I kind of viewed it as, well, maybe this is my last time on Dave because the Conan people might not be into it," says Kiley. "So I don't know."

Kiley thinks moving the show from New York to Los Angeles may bring some other changes. He thinks the Tonight Show's L.A. crowd might be a bit older than Late Night's typical college-age audience, and notes they have already "retired" the Masturbating Bear character, played by fellow writer Michael Gordon, with whom Kiley shares an office.

"There are times where he's rehearsing a bit and then there's a break," says Kiley, "and he's upstairs in the office and he's got the Bear costume on except for the head. He's sitting there in the costume, he's got the diaper on, and he's typing away."

Conan and company will clearly have a period where they are testing the waters. Who knows, they may find they don't need to change much. "I'm also curious," says Kiley. "I know that it's 11:30 so we have to kind of tone things down a bit, but also, in this day and age, things are much more out there, too. So we might not have to tone things down as much as we think we might."