Jon Cryer decided that acting was for him when he was still in his single digits, which is pretty easy to do when both of your parents are actors. Over the years he’s proven himself formidable on the stage (Torch Song Trilogy, Brighton Beach Memoirs), in films (Pretty in Pink), and — most recently — on the small screen, spending 12 seasons as Alan Harper on CBS’ Two and a Half Men. With over three decades worth of stories as a professional actor at his disposal, Cryer sat down and wrote a memoir, So That Happened, which is in stores now, and in addition to giving our Lucky 7 a go, he discussed the process of putting his book together, the likelihood that he’ll be bringing back Duckie, and whether or not he’s hoping to hear from Charlie Sheen anytime soon.
How long had you toyed with the idea of looking back on your life and times before bringing So That Happened to fruition?
It had not occurred to me at all. My agent and manager had said to me, “Hey, we think we can get you a book deal. Have you ever thought about that?” And I said, “No, I haven’t thought about that, because I don’t want to do it.” And they said, “Well, we think we can get you one.” I said, “I don’t think you can. I disagree. But if you can get me a book deal, I’ll write a book.” Cut to them saying, “We got you a deal,” and me suddenly having to figure out something to write about. I didn’t know if was just going to be a fun collection of essays, if it was going to be a comedy book, if it was going to be a tell-all about all the dark secrets of Hollywood that I know. But in the end, I realized that what sort of defined my life — and what certainly defined my career — was that a lot of just really absurd shit happened to me, and I thought, “Oh, well, there’s my show biz experience!”
One of those experiences involved attending a party at the Playboy Mansion, the nutshell summary of which is that you struck out, but you still met Tony Curtis.
Right, so can that really be considered a flop? I had always imagined the Playboy Mansion as just this non-stop bacchanal with every major movie star of the time, where you’re going, “Oh, there’s Jon Voight having sex with the entire USC cheering squad!” That’s what I imagined. But as you’ll read, that is not what occurred. But I did meet Hugh Hefner: He was bedecked in his robe, and he was charming.
When you were making Pretty in Pink, whose acting choices did you find the most flustering: Molly Ringwald’s or Harry Dean Stanton’s?
You know, I was disjointed the whole time working with both Molly and Harry, because all of their work is inner. It’s all super small and subtle…and as you know, that’s not me! Their choices were so much more filmic than what I normally did that it was a real adjustment for me. I think Howie Deutch, the director, wanted that tension, and that cobbling these elements together created the conflict he was going for.
The film initially had Andi ending up not with Blane but with Duckie. Do you ever wish they’d kept it that way?
You know, I’ve obviously gotten so much good will from Duckie partisans over the years — people still come up to me wearing Team Duckie t-shirts — but, nah, I honestly feel like it’s for the best. I think part of what made him so memorable was his status as the underdog, and in the end, I think that was one of the best things about him.
You talk in the book about not wanting to spend your life reprising the role of Duckie either spiritually or literally, but you’ve done it on a couple of occasions.
That is true. I did it for Mr. Show, where I worked with a chimp named… Was it Mr. Bananas?
I believe it was Dr. Bologna.
Dr. Bologna, yes. Please forgive me. Funnily enough, his acting choices were also very small and very filmic. But I don’t think I’m going to be pulling Duckie out of mothballs again. I feel like it was great fun to do it on Mr. Show, and then as a final goodbye salute on Two and a Half Men, but I don’t suspect I will don that chapeau once again.
Now, be honest: How many people do you think are going to pick up the book, flip straight to the stuff about Charlie Sheen, flip back to read about Pretty in Pink, and then start from the beginning?
You know, what’s funny is that my editor was saying the whole time, “You know that’s what people are going to do. You should just put it in the chapter headings what’s what.” I said, “No! I’m purposely going to have very obscure chapter headings just to ward that off!” I’m hoping that people approach the whole thing as an experience, because I put a lot of work into making it a narrative that makes some sense. I think just taking it in its individual parts might diminish it somewhat, so I hope people don’t do it that way.
You probably always suspected that the down and dirty details of Charlie’s meltdown were going to be used to tease So That Happened, but when the excerpt from the book was released in The Hollywood Reporter, how did you feel about the reception?
Well, it’s a little exasperating that the Charlie Sheen stuff is three chapters out of 27, yet that’s what gets all of the attention. I mean, there’s a chapter where I talk about the fact that I had cancer, but nobody cares about that. They’re, like, “You were with a prostitute? What?!?” But you never know what people are going to take away from things, and you never know what the press is going to play up.
Speaking of the prostitute story, hopefully your wife (Lisa Joyner) knew about that before she read your first draft.
Oh, yes. I was straightforward with her very early about that. But the Hollywood Reporter article actually came out a week before I expected it, so when I picked up my son that day, I had to have a very uncomfortable conversation with him. Thankfully, he hadn’t heard about it yet, so that was good, although he did have a weird reaction. He said, “Oh, yeah, well, I guess I’m not surprised.” I was, like, “Wait, what?”
So have you heard from Charlie since the excerpt starting making the rounds?
No! And I expected to hear something. But, no, not a word, which…I guess is good?
Do you hope to hear from him at some point, either about the book or otherwise?
You know, I… I don’t have any feelings about it. I really don’t. It’s been such a long, torturous road. I wish him well. I hope that maybe someday he decides he wants to be sober again. That would make me really happy. But he’s living his own life.
What was your first encounter with Playboy?
The Bo Derek issue is etched in my memory, and I remember it was a big deal to get the Bo Derek issue, because it was just massively popular. So it involved some sort of Mission: Impossible type plan — I believe we may have rappelled in on ropes — to obtain a copy. But I treasured it. She’s a very special woman.
What movie scared you most as a kid?
The scariest movie to me was The Exorcist. I think I was, like, 12 when that came out, so I was too young to see that movie, but I saw it. I’m pretty sure it holds up, too. I saw it pretty recently, and it’s still deeply disconcerting. So good on you, William Friedkin.
What was your first car?
My first car was a Maserati. When I shot Hiding Out, my character drove a Maserati, so I bought the car from the production. And I soon learned that Maseratis are not particularly dependable when the clock in the dashboard actually popped out into my lap. I remember taking it in to be repaired once, and I’m not 100% sure that this happened, but it appeared that the mechanic took out a part, set it aside, closed the hood, and then said, “You’re good to go!” Like it was something that the car never needed in the first place.
Who was your first celebrity crush?
Lynda Carter. And I know I’m not alone in that one.
Let’s pretend you’re on death row: What’s your last meal?
A serious In-n-Out Burger binge. When I’m being a good person, I’ll just do the In-n-Out burger and a Sprite. But if I’m on death row, I’d do the Double-Double instead, with a milkshake.
What’s your favorite mistake?
Oh, well, it’s definitely got to be Superman IV. I’m a part of superhero lore, in the worst Superman movie ever made, and that’s a badge I wear with distinction.
What did you buy with that first big check?
You know, I’ve actually been lucky enough to have a lot of big checks, and when they just get bigger and bigger, it doesn’t feel like your first one, but it’s, like, “Oh, this is the first time I’ve ever made this much!” So they all feel like a first big check. But what was the first thing I splurged on? Well, when I was a bachelor guy in New York and I was running in Brighton Beach Memoirs, which was my first big gig in a Broadway show, I, uh, filled my house with black lacquer furniture from Macy’s. Because I thought it looked cool! And some of it had a little switch on it, and when you turned it on, it would light up. Hey, it was the ‘80s. It was a very special time. But, you know, my favorite thing that really says “the ‘80s” to me is in Wall Street, when Bud Fox finally makes it and you see his fabulous apartment, it’s one of the most grotesque things ever. It’s just horrible. It was the apex of ‘80s design. You know, you’re supposed to go, “Oooooooh, he’s really made it now!” But it’s awful.
Once again, it all comes back to Charlie Sheen.
Yes. Yes, it does.