Jon Cryer on the Incredibly Long Life and ‘Absolutely Crazy’ Finale of Two and a Half Men

12-year role has been '87% blessing, 13% curse'

When he landed the role of Alan Harper on CBS' Two and a Half Men in 2003, Jon Cryer says he had "an unusual sense of confidence" that the show would break his streak of four failed TV series. It did a lot more than that, of course. After 12 hit seasons, Two and a Half Men closes shop on Feb. 19, going down in history as television's longest-running multicamera comedy. Shortly after shooting the final episode, the actor spoke with Adweek about the shrouded-in-secrecy, "absolutely crazy" final episode, the Charlie Sheen chapter and how Ashton Kutcher stepped in and revitalized the show, and what's up next.

Adweek: What was filming the finale like?

Cryer: It was very emotional for everybody. The writers had a huge challenge because they had to basically end two shows and somehow weave them together. And they seized upon a very meta concept and really ran with it. So it's unlike any show we ever did before—and frankly, unlike any series finale I've seen.

The title of the final episode, "Of Course He's Dead," seems to tease the return of Charlie Sheen. Does he come back?

I can honestly say I don't know because there were chunks of the finale that I was never allowed to read. Nobody got any piece of the script that they didn't 100 percent need, so I have not read the final tag of the show. They didn't even tell me they were shooting it! They shot it on another stage. I've said in the past, the amount of bridge-repairing necessary to make that happen, I thought was incredibly daunting and unlikely, but stranger things have happened in show business. 

Jon Cryer says goodbye to the show.  

The last long-running CBS sitcom to wrap, How I Met Your Mother, had a very divisive series finale. How do you think fans will react to yours?

I have no idea because it's a really unusual take on the show. It's in the same spirit of the show, but it really goes absolutely crazy. Everybody I know who's seen chunks of it feels it's very entertaining. But as I said, the show is almost two shows, so I think it would be impossible to satisfy the fans of both. 

TV has changed so much in the past 12 years. Why was Men able to endure when so few other sitcoms did?

It's very old school. We were doing an old-school sex farce, unapologetic, and I think one of the reasons that it was able to maintain an old-style broadcast audience was because that's what it was. It's a certain amount of luck that you just happen to hit something that really resonates with people and you're able to maintain this for a while.

At what point during the run did you exhale and realize this is going to be around for a while?

It took a couple of seasons. Once Everybody Loves Raymond was off the air and we were on our own in our time slot and we were still doing really, really well, that's when I felt, 'OK, this is going to last.' And of course, that's when Charlie got a divorce and suddenly things were starting to change. I had a good period of a couple of years where things were really humming along—and that's when all hell broke loose. 

Behind the scenes at the Two and a Half Men finale

When Charlie got fired in 2011, did you think that was it for the show?

There were so many things to process at that moment. The biggest one, of course, was I was worried about his health. He appeared to be spiraling. And then you start to think, 'OK, well, I guess I'm done. I don't see how the show goes on without him.' But then I also thought, 'Well, perhaps this is some tough love and he'll get clean and they'll start the show up again in the fall and hire him back.'

That didn't happen. Instead, you were able to add Ashton Kutcher to the mix and your ratings were higher than ever. How was the show able to pull that off?

You hear this quote all the time in comedy, but it's the writers. They always went with, how do we make the elements we've got the best they could possibly be? So instead of just trying to fit Ashton into the part as they imagined it, they always were trying to massage the part for Ashton. I think in a lot of other situations, producers and writers would just try to shoehorn a new performer into the predefined comedic dynamic that they wanted, but that wouldn't have worked. And it's that kind of thinking on your feet and not having a predefined idea of where the show is going that really saved it.

In hindsight, do you feel like that injection of new blood helped the show get to 12 seasons?

Yeah, that's probably correct. Working with Charlie had proved unpredictable at best. I don't know how long the original version of the show could have lasted by itself. You could absolutely argue that the new blood was what extended it.

Now that the show is over, what are you going to do next?

I've got a book coming out in April. It's called So That Happened, and it's about all the strange things that have happened to me over 30 years in show business. I'm going to be producing television, but I've always been just waiting for the next right thing, whatever it is. When I was writing the book, the publisher said, 'Do you want to muse about the future?' And I realized, no, I don't want to. Part of what kept me very happy in working in the entertainment industry is that I just take things as they come. I don't have a plan, and I don't have an expectation. I just roll with whatever happens next. 

Two and a Half Men is TV's longest-running multicamera comedy.

Would you want to do another sitcom?

Any actor who's worked in front of an audience in the format of situation comedy falls in love with it. It's a way of working where you're really connected to an audience, where you get that every Friday night but you can still have a family. It can be the best job on the face of the Earth. So I'm certain that I will miss that and want to come back to it at some point. I would also love to give America a chance to miss me!

As you learned early in your career with Pretty in Pink and playing Duckie, there can be a blessing and curse to being identified with one iconic role. Are you worried about going through that a second time with Alan Harper or do you feel like, 'I've got past it once, I'll get past it again'?

Exactly. That is the benefit of having had a character that resonated with people back in 1986—that I've gotten past it before and I will get past it again. I feel like it's 87 percent blessing, 13 percent curse. Having something that resonated with people that they really took to their hearts is such a luxury for an actor, and I'm never going to regret that. If I'm not getting certain parts because people are used to me as Alan, there'll always be something else to do, so I'm not really too worried about it. Also, as an actor you get to subvert that somehow. If in two years I play a terrorist, people will be like, 'Whoa, Alan is a terrorist!' And filmmakers and writers can have fun with that. It's almost never a bad thing.

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