Though it’s been a while since they last worked together, Jon Cryer and Charlie Sheen remain synonymous for their work on Two and a Half Men. Sheen and Cryer – who played siblings Charlie and Alan Harper, respectively – had great chemistry. And, for eight years, that helped propel their sitcom to success. That changed, however, when she experienced a string of personal issues and was ultimately fired from the show. Cryer has more recently shared his recollections of working with his former co-star. On that note, he recalled how he and Sheen got along during their time on the comedy and explained how their work dynamics changed when he faced his addiction struggles.
Jon Cryer discussed his over five-decade career when he appeared as a guest on the WTF with Marc Maron podcast. While strolling down memory lane, Cryer eventually talked to the eponymous host about his time on the hit CBS series (which is streamable with a Peacock subscription). The 58-year-old actor recalled just how “badly” CBS wanted Charlie Sheen for the show due to his work on the later seasons of Spin City. It sounds like the two co-stars got along relatively well. To that point, Cryer, who (like his character) was going through a divorce when the show started, recalled an on-brand request Sheen made him at the time:
There was a very funny moment. I was getting divorced at the beginning of Two and a Half Men, just like my character. I was in the midst of a divorce when that first started. And, at one point, Charlie – who is still married to Denise [Richards] at that time – said, ‘Hey man, if you need a place to stay, you can come stay with us.’ And I was like, ‘How much like the show do you want your life to be, Charlie?’ [Laughs]
That’s definitely an ironic offer if there ever was one. However, it’s hard to argue that it was generous given the position the actor was in at the time. The Pretty in Pink actor went on to explain that he and Charlie Sheen weren’t massively close off camera but did hang out here and there. They even bonded over a specific real-life experience at one point. However, it would seem that the relationship eventually changed once drugs came into the picture:
We had dinner together a few times. We didn’t hang out every night. … We were very different kinds of guys. And then his marriage fell apart, so we were both single for a little while, and we commiserated about that a bit. Then, [and] this happened with a lot of my friends growing up, whenever they got into drugs, because I was not into drugs, they split off and kept that part of their lives away from me, because they always just thought of me as a boy scout, I guess. And Charlie was the same way. He never talked to me about that stuff.
It was during Season 8 that Charlie Sheen began to make headlines, as he was reportedly partying with porn stars and prostitutes and using cocaine. Jon Cryer can still remember the changes in his co-star’s behavior at the time. And, during his chat with Marc Maron, he provided some additional details regarding the events surrounding Sheen’s exit:
Interestingly, he was still good at the job, and he was still a nice guy to be around. He didn’t like, take it out on everybody. He didn’t like, show up and scream and yell. In the [eighth] season, you could see that something was up. … I was a little worried about his health. His timing was a little off, but he had started using at that point, and stuff was starting to fall apart.
It was at that time that Charlie Sheen made disparaging remarks about TAAHM co-creator Chuck Lorre as well as Jon Cryer, who he referred to as a “traitor” and a troll. (Though he retracted his comments about Cryer shortly after making them.) More recently, Sheen has been candid about that period in his life, noting that “everything turned to shit.” However, he and Lorre ended their feud and have since reunited for the single-camera comedy Bookie (which can be streamed with a Max subscription).
As for the Superman IV alum, he’s not quite sure about reuniting with Charlie Sheen but wouldn’t “close anything off.” While appearing on The View (as shared on YouTube), he said that while he’s hesitant to be in long-term “business” with Sheen again, a “one-off” collaboration could happen. We’ll have to wait and see if that actually happens, but I’m sure fans would love for the two actors to work together again and re-establish their relationship.
You can currently catch Jon Cryer on his latest sitcom, Extended Family, which airs Tuesdays at 8:30 p.m. ET on NBC as part of the 2024 TV schedule.
