Jon Cryer is among the many celebrities promoting memoirs this season. His book is called So That Happened and we previously covered an extensive excerpt in which he told his side of Charlie Sheen’s spectacular meltdown and revealed that he (Cryer) once hired a prostitute at Sheen’s recommendation.

During Cryer’s promotional tour he debuted a new look, with a shaved head and facial hair. It really suits him. In a new interview with Entertainment Tonight (video is here), Cryer revealed that he dated Demi Moore in the 80s (they starred in 1984’s No Small Affair) and so he found it strange to meet Ashton Kutcher for the first time, on the Two and a Half Men set. Cryer kept expecting Kutcher to bring up their mutual ex, but it doesn’t sound like he ever did.

On Charlie Sheen’s meltdown
I don’t recall in the history of television that a star went so spectacularly off the rails.

In the first few years of the show Charlie was sober and he was married to Denise Richards. He was an incredible coworker. That was what made the meltdown all the more scary.

When he realized that Charlie was unmanageable
For me the big indicator was [when he got] arrested in Colorado [in 2009]. When that happened, I knew he was no longer sober.

On if he felt that he could help Charlie
Because Charlie and I didn’t really bond over drugs… that part of his life he didn’t really let me into. So I tried, but Charlie made the choice that that [sobriety] was not the life he wanted anymore.

Why it was awkward to meet Ashton Kutcher
It was awkward because I didn’t know if [Demi had] even told him that we’d dated. So at our first meeting, we’re trying to have that ‘hey let’s create some chemistry’ meeting, when all the time I’m looking at him… waiting for him to drop the bomb.

The first season of Two and a Half Men I got a divorce. The second season Charlie got a divorce. So I thought that after a season of Two and a Half Men that it was probably appropriate that Ashton got a divorce.

On having to tell his son he had hired a prostitute in the past
I found myself picking my son up at school and having to give him a heads up that, ‘Oh, you might read something on the Internet today that’s a little curious.’ So I told him the facts of it, and he said, ‘Yeah, I’m not surprised.’ I was like, ‘Wow, okay!’

[From ET Online]

I didn’t realize that guys found it awkward to have dated the same woman. I thought that they usually bro-bonded over that sort of thing, but I guess everyone is different.

Cryer’s son, Charlie, (from his first marriage to British actress Sarah Trigger) will turn 15 in June so I guess he’s old enough to hear that his dad once hired a prostitute. I hope Cryer explains to him that it was a mistake and that he doesn’t endorse it at all though.

Cryer also said that he used to be mistaken for a gay guy and that he changed the way he sits so that he looks more masculine. He’s talked about this in the past. Last year he said that everyone assumed he was gay when he was a teenager, and not just because he played Duckie in Pretty in Pink. He claimed to strongly identify with Duckie and called himself an “effeminate heterosexual dork.” I’ve known guys like that.

Not everyone knows that Cryer rose to fame in the classic John Hughes film. In an appearance on The Jimmy Fallon show yesterday, Cryer played charades with Michael Douglas. Douglas failed to guess “Pretty in Pink.” That’s at about 4:00 into this video. It’s clear that Douglas had no clue. Spoiler – the other team, with Kat Dennings and Fallon, won.

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