Actor Jon Cryer on Charlie Sheen, Ashton Kutcher, and Pretty in Pink

The man who survived eight years of Charlie Sheen and 25 years of being called “Ducky” talks porn, paparazzi, and spoiled chocolate milk. 

We assume people still call you Duckie on a daily basis. 

Yup. It’s hard to be cool when people are yelling “Duckie!” at you, but I’m so glad people took that character to heart.

You’ve starred in several TV shows that never made it past one season. What made Two and a Half Men different? 

I have not come away with any real understanding of how this all works. I just show up and try to find the joy in every situation.

The show has had some great guest stars over the years: Sean Penn, Carl Reiner, Ken Jeong, Megan Fox… 

People forget that Megan Fox played an incredibly hot 16-year-old on our show, and even at the time we all had a hard time looking at her. It was best to ignore her and go about your business.




How’s it going now that Ashton Kutcher has joined the show? 

It’s great. Ashton is an actor who has no pride or dignity, much like myself, so we’re two of a kind. I can’t say I saw this all coming, but every now and then it’s good to have an enormous challenge thrown at you.

Word is he has a sick trailer. 

Oh, yeah. The first floor—and there aren’t many trailers where you can talk about a first floor—is a dressing room and office, and the second floor is a club.

A club? Like, with a bouncer? 

Ashton has an open-door policy. I think he’d make a very scrawny bouncer, not that he’d ever try it.

Does he know you made out with his wife, Demi Moore, in the movie No Small Affair? 

We don’t really talk about it, because when I made it Ashton was seven. It’s not his demo. It’s mild, anyway. I don’t think it would be too disturbing to him.

Back when all the craziness was going on with Charlie, did people offer you cash in back alleys to spill what you knew? 

Nobody offered me money, but I did get paparazzi outside of my house, which was a rude shock. But there are only so many articles you can run about a guy cleaning out old chocolate milk boxes from the back of his Volvo.

After Charlie started calling you names, what made you decide to go on Conan and “admit” you are a troll? 

I realized there was a point at which the situation became so bizarre that it had to be dealt with comedically. You know, it was literally the same day the tsunami hit Japan, but because the Internet is such a ridiculous place, a major news site’s main page read TSUNAMI STRIKES JAPAN! and right below it was JON CRYER: “I AM A TROLL.” 

Any wild Charlie stories? 

When all the craziness was going on, I texted him, “You’ve got to see The King’s Speech,” and we had a long text conversation about the performances. Turns out he was at a porn convention and was texting from underneath a pile of naked porn stars.

Is it true Charlie was considered for the Andrew McCarthy role in Pretty in Pink? 


That is my understanding, yes. And Robert Downey Jr. was up for my role! You know, a lot of people still consider the ending of Pretty in Pink a great injustice. I can see why John Hughes decided to reshoot the ending and have Molly Ringwald’s character end up with the rich guy instead of Duckie. I mean, the dynamic between Molly and me was not incredibly sexual. 

Molly has said, in fact, that she thinks Duckie was actually gay. 

I wasn’t going for that, but if that’s how she feels, OK! At one point she joked, “If he was real, he would’ve come out by now.” I was like, “I’m not so sure…”

How was making Superman IV? 

I had a blast—I was a 22-year-old kid working with Gene Hackman on a Superman movie—but I also sensed that something was wrong, because huge chunks of the script were being cut, and the special effects were looking incredibly cheesy. I remember Christopher Reeve told me, “They ran out of money.” I said, “But it’s gonna look terrible!” He said, “I know.”

We hear you read for the role of Chandler on Friends. 


Yes, there’s a videotape of it that I hope never sees the light of day. I was in London when I did the audition, which was terrible, and the tape got stuck in customs. Only later did I learn that they didn’t see it before they picked Matt Perry. I think everyone is better off.

What do you wish you could tell your 18-year-old self? 

Buy Apple.

What’s the one thing to remember in a fistfight? 

Litigation solves everything.

Finally, what’s the most important thing you’ve learned about women?

You’d be amazed at the power of complimenting the footwear. Try it. You’ll see.

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