In these engagements, which feature the famed nine-member Los Angeles-based comedy troupe (best known for their Funny or Die videos), Carey emcees, participates in the group's sketches, and even breaks in some new material for his stand-up act. He recently took time with TheaterMania to chat about this project, his thoughts about the nature comedy, and what Broadway show he'd drop anything to see.
THEATERMANIA: Are people going to be prepared for The Best of the Midnight Show? This group is known for doing some really wacky stuff.
DREW CAREY: The first couple of sketches are super silly so people know: OK this is going to be a weird show. It puts them in the frame of mind where they just accept everything that's crazy. You have to do anything you can do to get audiences in a simple, playful spirit. Even when you're telling jokes, the trick is to take everybody as close to the edge as you can to create tension. The more tension, the funnier the laugh when the tension is broken -- but you can't go over the edge. Once you go over it, you break the spirit of play. You can get away with jokes about death and cancer and whatever, but you have to do it in the spirit of play.
TM: Do you have a preference among doing improv, sketch comedy. or stand-up?
DC: There are so many styles of comedy and every style of comedy pleases different people. I'm actually a better stand-up comic than anything I do. There are people out there that think certain styles of stand-up are old fashioned and boring. Others think some are too dirty. It's the same with music or anything else; there is a different style for everybody.
TM: Improv seems like a very different animal, because what's funny in the moment isn't always funny later on. Do you agree?
DC: Yeah. I don't know if you ever watched my show Whose Line Is It Anyway?, when those guys would make up these songs, but it's really amazing to watch. People go, "Oh, that's my favorite part of the show" and "We love when those guys make the songs." But if I were to print out the words to the songs and send them to you, you probably wouldn't think it was funny at all. However, the idea that you're watching somebody make it up and all this stuff is happening in context all at the same time makes it really funny.
TM: Speaking of songs, you've dipped your toe into musical land. You did Stephen Schwartz's Geppetto on television and you also did Hairspray in concert at the Hollywood Bowl. Do you enjoy doing musicals?
DC: I had a lot of fun in Hairspray. I was with Harvey Fierstein, and it's hard to lose when you're playing opposite him. I played his husband, Wilbur, but it wasn't really like a vocal stretch or anything.
TM: Was that your first live musical?
DC: When I was in the ninth grade, I was in The Pirates of Penzance. I played Frederic the Pirate prince. (Laughs.) I gotta have a picture of that on my Facebook page.
TM: Have you given any thought to doing another stage musical?
DC: I've been offered stuff, but I always say "No" because they always want a three-month or six-month commitment, which I'm not prepared to do. It would be really fun, but I can only do so many things.
TM: If we could strip away the time commitment obstacle, what Broadway show would you do? DC: It wouldn't matter as long as it's funny. Right now, though, my favorite Broadway show is The Book of Mormon, but there's no part for me in it. I wouldn't be able to play any of those parts, because they're all young missionaries -- or Black -- and I'm not that young. It's the greatest musical I've ever seen in my life. Every time I go to New York, I make sure I see it. I'm gonna see it when it comes to L.A. this fall, because I'm anxious to see what the new cast does to it. And if it ever goes to Salt Lake City, man, take a flight.