Charlie Sheen's final days on Two and a Half Men clearly weren't the most positive, especially behind the scenes. However, Sheen did get a lot of support from his former colleagues. Among them, included Holland Taylor, who praised the actor for his generosity.

Another notable name on the show, Melanie Lynskey had only positive things to say about the actor, and the way he treated her during their time together on the series.

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It's a shame Sheen didn't get a proper send-off or return to the show. In truth, Charlie's idea for a return sounded a lot better to what Chuck Lorre had planned. From a creative standpoint, Sheen might've been right to have skipped out.

In the following however, we'll take a look at a different topic, and that's Charlie's relationship with Jon Cryer. We'll reveal the ups and downs between the two, including Cryer dating one of his exes.

Jon Cryer Revealed Charlie Sheen Was A Completely Different Person During The First Few Seasons

Charlie Sheen
Instar

At the start of Two and a Half Men, Charlie Sheen was a completely different person to work with, at least according to his co-star, Jon Cryer. The actor revealed that working alongside Sheen was a great experience for everyone early on.

"In the early years, the life with Charlie Sheen was great," Cryer tells Entertainment Tonight. "We got along great, he had been sober for two years when we started the show, and it was really important to him to keep sober. And for those first few years, the show was also going so smoothly."

"He just had it straight out of the box like it was genetically programmed into his body. That was fun and very self-assured," he said. "For those first couple of years, it was, you know, an incredible joy."

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Cryer would even look back on a Vegas trip the two took early on to promote the show. Cryer was expecting a party-type of trip from Sheen. Instead, it was early nights and lots of rest for the actor.

Along the way, it would all start to change behind the scenes.

Once Charlie Sheen Admitted He Had Dated Jon Cryer's Girlfriend, Their Relationship Ended

It was like an episode of Two and a Half Men in real-life as according to Cryer, both Sheen and the actor became single at the same time. Now here's where things get interesting, according to Cryer with THR, he had met a girl at a party, who later became his girlfriend.

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Upon meeting Charlie, Cryer's ex-girlfriend admitted to knowing Charlie from her days as a waitress at, La Moustache.

Cryer didn't make much of the situation, however, he was soon after approached by Charlie, who had a confession to make.

Cryer recalled the situation, and everything Sheen had said. "Hey, listen, we gotta talk. I’ve been talking to my therapist because I don’t know if I should say anything. I’ve been agonizing about this, dude, really. I … I don’t know how to say this, but … Stephanie and I used to date.”

Charlie tried to downplay the situation, telling Cryer it wasn't serious. When Cryer asked how the two had broken up, that's when he decided to break up with her himself.

Charlie said, “Well, I wanted to bring another girl into bed with us, and she was not happy about that.” And then he looked me straight in the eye and with no trace of irony, said, “So heads-up on that.” I went home that night and broke up with Stephanie.

Unfortunately for Cryer, things would get even more complicated alongside Sheen.

Charlie Sheen Started Going Off The Rails During Season 8 Of Two And A Half Men, According To Jon Cryer

Angus T Jones and Two and a Half Men cast
Instar

Behind the scenes, issues were starting to arise with Charlie Sheen's health. Early on, Chuck Lorre asked Cryer to check on Sheen. Despite casual convos between the two, it was clear Sheen wasn't in the best of places.

By season 8, Cryer revealed that it was obvious Sheen was struggling with addiction issues.

"Charlie didn’t look so good as we started our eighth season in fall 2010: gaunt, pale, sallow, even sweaty occasionally. He started talking to himself. Most of all he just looked thinner, in a not-good way."

Cryer continued, "His timing started to go off, too. He was rushing lines. Charlie just wasn’t hitting the jokes the way he used to."

We all know what happens next, as Sheen eventually left the show and clearly, Two and a Half Men was never the same again.