Jon Cryer Reveals How Close Two And A Half Men Came To Ending Amidst Charlie Sheen Going 'Off The Rails'

Alan and Charlie Harper in Two and a Half Men
(Image credit: Warner Bros. Television)

Two and a Half Men was a hit for CBS from the early days, with sitcom veteran Charlie Sheen headlining opposite Jon Cryer. The two anchored the series for the better part of a decade, before Sheen’s very public departure. He was fired in 2011 after eight seasons, with the eighth season cut short after Sheen entered rehab and made some controversial comments. The show ultimately continued with Ashton Kutcher joining Jon Cryer, but Cryer has now explained how close Two and a Half Men came to actually ending early. 

Speaking with ET, Jon Cryer revealed that the show was “going so smoothly” in the early years (which you can revisit streaming with a Peacock Premium subscription), and Charlie Sheen had been sober for two years before starting. Things changed over the years, however, when Sheen started going “off the rails.” Cryer – who would go on to land a memorable role on Supergirl – reflected:

[I]n later years, when we started noticing things were getting stranger for him, and his marriage fell apart, he was still lovely to work with, he still showed up on time and knew his lines and was doing the job. But you could tell that there was some trouble brewing. He started to have issues with the writing and sometimes issues with the writing that I didn’t understand. I would say, 'This is the kind of joke you had no problem with a year and a half ago, and suddenly now it's an issue?' So, you know, it was very subtle. It took a while before it started really going off the rails.

Charlie Sheen went through his divorce from Denise Richards during his time on Two and a Half Men, which lasted from 2003-2011. Their split was finalized in 2006. He married Brooke Mueller in 2008, but they too divorced in 2011. According to Jon Cryer, Sheen’s personal life began to affect his work on the CBS sitcom, and the issues that ultimately led to his firing were “very subtle” to start.

The ultimate decision to cut Season 8 short and fire Sheen came after what was reportedly an erratic final day of filming. At that point, the odds seemed in favor of the show ending rather than continuing without the star. As much as Jon Cryer was a co-lead with Sheen, the premise of Two and a Half Men seemed to require both Charlie and Alan Harper. 

Now, Cryer has shared that as his co-star’s public behavior grew more and more unpredictable, he and the creator considered ending the show altogether. He said: 

I think there was a moment where Chuck Lorre and I were looking at each other and we said, 'It's not worth this show going on if going on enables Charlie Sheen to kill himself. If giving him enough money to do whatever the thing is that ends his life, you know, we don't want to be a part of that. And I think, actually, when Charlie was let go from the show, the first thought amongst most of us was, 'OK, we're done. This has been a great thing but we're done at this point.

A show running for eight seasons is pretty impressive as is, so Two and a Half Men wrapping at the close of even the shortened eighth season wouldn’t have been terrible. Cryer was evidently willing to let it happen if it was best for Charlie Sheen’s health, but Chuck Lorre (who recently opened up about watching the show again after the drama) came up with a different kind of fix: seemingly killing off Charlie Harper and bringing in Ashton Kutcher as the new co-lead. He and Cryer would star in the final four seasons of the show before it finally ended for good in 2015, with a finale that revealed Charlie Harper was alive after all.

In the years since the end of Two and a Half Men, Jon Cryer evidently hasn’t kept in touch with Charlie Sheen, but said that he is “glad that his health has rebounded” and hopes for “nothing but success for the guy.” Recently, he took to Twitter to pitch a reunion with Sheen for another Hot Shots! movie. The first Hot Shots! was actually the first time that the two actors appeared in the same project, more than a decade before they’d reunite for Two and a Half Men. Whether or not they truly ever reunite for another project remains to be seen, but Cryer is heading back to TV comedies following the end of Supergirl.

Laura Hurley
Senior Content Producer

Laura turned a lifelong love of television into a valid reason to write and think about TV on a daily basis. She's not a doctor, lawyer, or detective, but watches a lot of them in primetime. Resident of One Chicago, the galaxy far, far away, and Northeast Ohio. Will not time travel, but will sneak references to The X-Files into daily conversation.