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Jon Cryer on Duckie, That Mr. Show Cameo, and His Next Move After Two and a Half Men

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It’s tough getting past your most famous role when it comes so early on in your career, and Jon Cryer can tell you all about that. Duckie, the New Wave rockabilly nerd who is obsessed with Molly Ringwald’s character in Pretty in Pink, has followed him even after he finished starring in one of the most successful sitcoms of the past decade, Two and a Half Men. In his new memoir, So That Happened, Cryer recounts what he calls the “escalating episodes of weirdness” that have made up his career, from acting onstage as a teen to his iconic role in the ’80s classic to the “multiple internet shitstorms that were Two and a Half Men,” and does it all in a voice that is entirely his; funny, sometimes irreverent, and always full of energy. With the book coming out today, Vulture spoke to Cryer about life after Two and a Half Men, Ferris Bueller envy, and what it takes to get him to giggle.

So what are you doing now that Two and a Half Men is over?
I’ll probably do more television, or just wait for something great to come along. I’d be happy to do another comedy, but I’d love to do a drama. Literally the week after the show was done, I got a call; Law and Order: SVU wanted me to be a serial killer. It turns out the showrunner — this is weird — used to be my babysitter. We grew up in the same building on the Upper West Side, and he used to be my babysitter. And I turned it down because there [were] some scheduling problems, and I felt terrible about it because I’m turning down my old babysitter!
You dressed up as Duckie for an episode during the last season of Two and a Half Men. A lot of actors try to distance themselves from their breakthrough early roles. That doesn’t seem to be the case with you.
I did have some issues revisiting Duckie. I did it once for Mr. Show because Mr. Show is fucking brilliant, but then I did it this time because it was taking the air out of it. I knew when I came onstage that the audience would applaud, and we took the air out of it when I was immediately mistaken for Ferris Bueller. It wasn’t reveling in it. But another thing that made me queasy about it is it’s not fun seeing an old guy pretending to be a young guy. That’s just depressing. I made the costume designer promise me that if I looked like an old guy pretending to be Duckie, she’d pull the plug on it.
How did the Mr. Show thing happen?
I used to go to tapings of Mr. Show, and I just got a call that David and Bob were asking if [I] could do a part, they’ve got a thing called “Monk Academy” that starts out as a take off on Little Buddha and then becomes an ’80s camp-movie parody. They said, “You drive up in an open-top convertible with a monkey.” So I was like, “Sure, I’m down with that.” And I got there, and I go into the dressing room, and there’s the Duckie outfit. And I’m like, “Oh. They want me to be Duckie. They did not say that to me when I agreed to do it.” I later found out that [the] guy who wrote the sketch was full of trepidation about it, he was really worried that I’d see it and freak out and say, “No way.” But I felt like the moment would be so surreal, with Duckie driving up with a monkey in an open-top convertible,that I said, “John, you have to do this.”
You talk in your memoir about your early career doppelgänger, Matthew Broderick, and how your careers took somewhat-similar paths. Was it strange for you to see him show up in a John Hughes film right after Pretty in Pink?
I will admit to some jealously at the time, only because I had heard Ferris Bueller was a great script, and anytime you hear that something’s fabulous and there’s a great part that you’re in the right age range for, you get a little jealous about it.
Pretty in Pink came out in the middle of this run where John Hughes redefined the teen movie. Were you disappointed that, unlike Sixteen Candles and The Breakfast Club, he wasn’t directing the film you were in?
It’s interesting because it was a John Hughes script, and it was considered something he was running from top to bottom. So even though Howie [Deutch] was directing it, the assumption was everything was coming from John. Even though John was not on the set everyday, he was the guy who said, “Let’s have you guys make up some of this,” which I was really surprised by. Molly was still 17 at the time. She wasn’t even legal, and to sort of entrust your multi-million-dollar movie to these kids saying, “You know, I don’t know if that line sounds right,” was a pretty gutsy thing to do. That’s where, “Blaine? His name is Blaine? That’s a major appliance, that’s not a name” came from.
You just ad-libbed that, didn’t you?
The original line was: “Blaine? His name is Blaine? Are you serious?” Which is, ya know, could use a little more oomph. The great thing was John established early on that he wanted these characters to feel comfortable with what they were saying, and if there was more that we could bring to it, he wanted to hear.
This might sound likes sacrilege, but I think those Hughes scripts that Howard Deutch directed were stylistically better-looking. Do you think Deutch doesn’t get the credit he deserves when people talk about ’80s teen movies?
Yes. Howie was a great director to work with. He made me feel confident as a performer, which is more difficult than it sounds. He did wonderful subtle stuff with Molly and Andrew, great stuff with Jimmy Spader and Annie Potts. He worked fantastically well with actors. And in some respects, Breakfast Club is an incredibly earnest movie, and Howie brought a little perspective to that earnestness that was good for John.
Why do you think you’re drawn to comedic roles?
Partially because I’ve always felt I was kind of a ridiculous human being. So when I get super dramatic, the urge to giggle nearly overtakes me. It’s the reason I think I haven’t been cast in science fiction, because the second you see me, you say, “Okay, I don’t buy this.” I actually ran into J.J. Abrams at the Emmys a few years ago, as he was about to shoot the first Star Trek movie, and I said, “I have to be in the movie in some respect. I just want to die entertainingly.” When the ship gets hit by a photon torpedo, I can just be the guy across camera going, “AAAAHH!” or whose console explodes. But he was not up for it; he said it would be distracting. It’s because I’m so inherently ridiculous that the second you see me going across the screen, you start laughing.

Jon Cryer on Life After Two and a Half Men