Jon Cryer Confirms What We Suspected About Charlie Sheen's On-Set Behavior

Charlie Sheen's time on "Two and a Half Men" became infamous for his behavior toward the end of his stint on the hit sitcom. The "Major League" star had a public drug addiction that involved a rift with network executives in 2011. Ultimately, Sheen was fired and his character was killed off on the show, per People.

Jon Cryer had a tumultuous ride with Sheen both on and off set, as the pair both found themselves single at the same time. The "Platoon" actor was known for spending time with sex workers, and Cryer, who was not ready to enter the dating pool, followed his co-star's lead. "He and I had different tastes, so I didn't go with his exact recommendations, but my forays into prostitution were about as awkward as you might imagine," the "Pretty in Pink" star wrote in a 2015 article for The Hollywood Reporter. Once Cryer did start dating, he ran into difficulties, as he recalled to THR that he started dating women only to learn that they had been intimate with his "Two and a Half Men" co-star. 

After Sheen left the show, he and Cryer grew apart. In 2019, Cryer said it had been "a couple of years" since the pair had even spoken. "It's kind of a roller coaster when you have Charlie in your life and I just haven't decided to get back on that roller coaster," Cryer joked to Access. Now, Cryer is speaking about how Sheen's behavior evolved over time.

Initially, Jon Cryer loved working alongside Charlie Sheen on "Two and a Half Men," as he was impressed with Sheen's comedic timing. "We got along great, he had been sober for two years when we started the show," Cryer told Entertainment Tonight on June 13. Unfortunately, Sheen started to show cracks on set as his personal life eroded, but the "Wall Street" star still maintained a level of professionalism. "Then, in later years, when we started noticing things were getting stranger for him, and his marriage fell apart," the "Big Time Adolescence" actor said. Cryer started to have concerns for Sheen's performance when his co-star began complaining about the writing. That was a precursor to Sheen's heavy drug use. "It took it a while before it started really going off the rails," Cryer added.

The fracas between Sheen and the network executives was stressful on Cryer and the production team. "It was one of the first internet s***storms, plus there's the fact that all of our jobs are tied into this guy, and we're all his friends," the "Hot Shots" actor told Entertainment Weekly in 2020. Although Cryer added that he was "thankful for the years that were great."

A decade after his infamous departure from "Two and a Half Men," Sheen took accountability for his actions. Discussing his behavior near the end of his tenure on the show, Sheen told Yahoo! Entertainment in 2021, "It was desperately juvenile."