Jon Cryer on Winning Two Emmys for ‘Two and a Half Men’

Jon Cryer is one of the few actors in Emmy history to win both a supporting and lead actor statuette for the same role. The show that made that possible, “Two and a Half Men,” ended its 12-season run on CBS earlier this year.

After losing to Jeremy Piven three years in a row, he wasn’t nominated when you won the supporting actor Emmy in 2009. Was that a relief?
I did not take a sick satisfaction from that, no, I don’t know what you’re suggesting. You know what, I still had zero expectation that I would be next in line. It did not ring any particular bells that Jeremy was not there that particular year. Mostly you’re relieved to be invited to the party. I still didn’t think I had a shot until Kristin Chenoweth won, who was sitting right next to me. For some reason that opened up the possibility in my mind. It was like, “Wait a minute, I can win.” I don’t know why, I don’t know what possible connection there was.

What do you remember about that night?
I remember going to the after-party, and there was Matthew Weiner, who had just won for “Mad Men.” He was like, “Hey Jon.” And I said “Hiii?” He said, “You don’t remember me, do you? I used to work on ‘The Trouble With Normal,’” which was a sitcom I did for ABC years before. He’d been one of the writers. To see someone from comedy bloom into this guy who’s making a series that’s literally transforming television, that was a lovely moment.

Was it something you had dreamed about?
I was such a TV baby. Growing up I parked myself in front of the TV, and it was always sitcom, sitcom, sitcom, sitcom. That’s what I lived as a kid. That I got to do it professionally was this incredible gift. Then that I got to go to the Television Academy and see the actors I loved as a kid — just run into Tom Bosley, Jamie Farr. Mike Connors did an episode of “Two and a Half Men.” I got to work shoulder-to-shoulder with these guys I loved. My greatest regret still is that I have not got to work with Carol Burnett. Someday I hope I’ll get a chance. I’ve gotten to meet her and talk to her and spend wonderful time with her, but the time when we’ve got to work together has not yet occurred. This stuff really does mean something to me.

Did you feel less pressure going back to the Emmys after you’d won?
Yes, I did. The (second win) I had changed categories (to lead) because it was the first year of the new “Two and a Half Men” and they were focusing more on Alan’s character. I was in with an astonishing group of guys and I didn’t for a minute think it was possible I would win it, and I commented on that in my speech. I said, “I am as shocked as you people. I have no explanation for this.” The character was such a crazy ride the whole time that I suppose I should’ve expected it only on the level of “The next ridiculous thing that’s gonna happen is you’re gonna win an Emmy for this. Again.”

Does it seem kind of random when you win or like you actually did a better job that year?
It does feel a little random. There are certain quirks of the process, like if you have a super-strong episode. For example, the last win for actor for me, I’m convinced that even though some of the nominees were way better overall than I was that particular year, I had one super-strong episode and that was the one the committee saw. So in some respects there are quirks in the process and times you just get lucky. They wrote a really grandstand-y episode for me. I happened to get nominated at the right time and it happened to be what (Emmy voters) saw.

The show had such a roller-coaster run; did the attention in later seasons help validate what you were doing?
Absolutely, you still want to feel relevant. But at the same time you figure it’s not always going to go your way. A friend of mine at one point said, “You’ve become a Him again.” He meant it as a compliment, but it does express what had to have been the exasperation of people that so many great new performances hadn’t been acknowledged. I totally get it on that level.

Were the Emmys your first real experience with awards?
I believe the Emmy was the first award I won since summer camp. At summer camp I cleaned up awards-wise, just so you know. I was the Meryl Streep of summer camp.

In which categories?
Best supporting actor. And then I moved up to leading actor and won again. I guess I really shouldn’t have been surprised.

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