SOME might paint Jon Cryer, 43, a perpetual romantic loser given his two most iconic roles -- lovelorn Duckie in the teen angst favorite "Pretty in Pink" (1986) and awkward single dad Alan Harper on "Two and a Half Men." But Cryer beat "Iron Man" himself (Robert Downey Jr.) for the Duckie role, stole the movie and comes close to doing the same on "Men." Some achievement given he's on screen with Charlie Sheen and child actor Angus T. Jones. Cryer, though, is a multi-hyphenated talent (actor-writer-director-producer) who won Broadway acclaim at 18 and later a fortuitous pairing with Sheen in the movie comedy "Hot Shots!" (1991). Unemployed and weeks from losing his home, Cryer badgered his agent to get him seen for the role of Harper. A nominee the last two years for supporting actor, this still comparatively unsung comedy player could score a hat trick.
What do you like about Alan?
I love him like you love your kid brother who keeps messing up. God love him, he tries. Alan would love it if there was actually order in the universe and I think I've got a little bit of that. The other day I had to find this incredibly specific screwdriver and it didn't take me but 26 seconds!
It bothers me that there is virtually nothing attractive about him. He's uptight, not particularly good-looking, not funny, not confident, doesn't have a steady paycheck. He has nothing going for him.
The sexual undertone seems quite racy for a prime-time network show.
I know. It's like, "Wow. This is naughty!" I stand back in awe occasionally. One of our jokes about oral sex made all my pores open.
And you don't mind the show's premise being contingent on Alan's not getting much sex?
No, because people are who they are. We'd like to believe people can really change and move on. Perhaps they do. But not Alan.
You must feel a little smug about your own stunning wife.
Well, my wife is awesome.
Is it true you spotted her on the street?
Yes. I thought, "That looks a lot like TV's Lisa Joyner" but kept driving because it would have been weird to stop. Months later I saw her again, stepping into a KCAL van, and thought, "Of course that's TV's Lisa Joyner." I left a note: "Hey, we met years ago. Here's my phone number, my cell number, my e-mail." She called, we went out and it was lovely.
You had to reshoot the ending of "Pretty in Pink," which famously saw you losing Andie (Molly Ringwald) to Blane (Andrew McCarthy).
The reason Molly was so halfhearted when we shot the first ending of the movie [with Duckie and Andie ending up together] was because she didn't for a minute picture herself with me as Duckie. She could buy it if he was Robert Downey Jr. but being that it was me, there was no way. I was like, "Wow, I had no idea she was completely repulsed." But OK, Mol, whatever floats your boat.
Did you and Charlie Sheen forge a friendship on "Hot Shots!"?
Not so much but I enjoyed his company. This was supposedly while he was still partying quite a bit, and, even loaded, Charlie was a great movie star. He'd show up on time, knew all his lines, was affable and friendly. Then he'd hop into a convertible with [porn star and then-girlfriend] Ginger Lynn and head off into the night. I have to say, I had a certain amount of admiration for that.
Things were different on the show?
The first season, I was going through a divorce and he was happily married. The second season, he was getting a divorce and I was single and looking. We did have a small overlap where we were both single. I even dated one woman who confessed to me after a while, "OK, I dated Charlie." That was just too weird.