At this point, if you’re not quick to trust the almighty Hugh Hefner’s judgment, you’re taste in beautiful women must hover somewhere above photos of either Janet Reno or Whoopi Goldberg (No offense, though—Sister Act is the shit!). Month upon month, the Playboy mastermind anoints one lucky knockout as the magazine’s “Playmate of the Month,” and, every year, one of the hot-twelve earns Hef’s highest honor, that of “Playmate of the Year.” And this year, he’s outdone himself yet again.

Early last month, the coolest man alive bestowed Claire Sinclair, the October 2010 issue’s “Playmate of the Month,” as his 2011 Playmate of the Year. Having just turned 20 years old last week, the buxom Los Angeles native is one of the youngest women to ever hold the title; so young, in fact, that the Las Vegas club promoters that hosted her coronation ceremony had to shuffle her out of the venue immediately after her acceptance speech, due to the rampant alcohol on the premises. See, not all girls have it that inside nightclubs.

Sinclair isn’t your typical Playmate of the Year, though. Aside from her uniquely pre-21 age, she’s a throwback to the old 1950s pin-up days of Bettie Page, whom Sinclair has idolized since she was a little girl; a time when sexy ladies posed in vintage lingerie for the sake of thumbtacks stuck into guys’ bedroom walls. In fact, Hefner has cited Sinclair’s nostalgically sexy look as the reason why he selected her as Playboy’s latest 365-day queen.

With her run as 2011’s Playmate of the Year officially underway, Sinclair came down from her well-deserved high to chat with Complex about just what the title entails, how being under-21 has spoiled some of the fun, her days as a costumed princess, and why immaturity in men really turns her on.

Complex: How crazy has your life been since Hugh Hefner made the formal announcement about your being 2011’s Playmate Of The Year last month?

Claire Sinclair: It’s been a really hectic, but great, month. I actually don’t mind being so hectic; I’d rather be busy then sitting around at home all day, you know? But, really, it’s more a sense of relief now. Like, “Finally, they’ve announced it!” It felt like I’d been waiting forever for them to make the formal announcement and for it to be official. So, I’m really glad that I lasted through all of the anxiety. [Laughs.]

claire-sinclair-hugh-hefnerHow long did you know about it before the actual announcement?

Claire Sinclair: A couple of months. Hef actually told me during a party at the [Playboy] mansion. I had to keep it secret, because the official announcement had been set for May, and it was just killing me. I kept thinking that everything could change, and they could take it away from me before anyone else even knew I’d won the title.

I was freaking out, because I’m one of the youngest Playmates of the Years ever, and I thought that they were going to change their mind. I’m too young, I can’t promote liquor—they’re going to take it away from me. So I was freaking out until the actual day of the ceremony, and it’d become official. Then, I finally breathed. I just thought, “Cool! I’m officially Playmate of the Year now—they can’t take it away.”

Did you or Hugh Hefner talk about the concerns with your age? Because I’d imagine that you technically won’t be able to attend some of the functions or handle some of the responsibilities that might involve things like alcohol or 21-and-over club entrances.

Claire Sinclair: Well, when he told me the news, I definitely didn’t want to bring my age to his attention. He knew I was really young, of course, but I didn’t want to be like, “OK, so are you sure you want this? I’m under 21, after all.” [Laughs.] He probably thought about it, and I wasn’t going to rub that in his face. I was just happy that, regardless of him knowing my age, he picked me.

The bad thing about it, though, is that since I’m under 21—and I think this is really silly—I couldn’t be on the cover of my issue. I shot the cover of my October issue originally when I was just a Playmate, the college issue, but it got rejected because I was under 21. When you’re on the cover of Playboy, you’re kind of promoting everything inside of it, so all of the liquor advertisers pull out if there’s someone under 21 on the cover. So both times that I shot the cover, I lost it. So, that was a little depressing. [Laughs.]

So you can’t get a Playboy cover until next year, then.

Claire Sinclair: Yeah, hopefully. I’m going to ask Hef, “Hey, for my birthday, can I be on the cover of Playboy?” [Laughs.] I think that’d be a really nice birthday present. They took it away twice, so the third time’s a charm, right? We can do a big cover with me holding a bunch of balloons, or blowing out 21 candles on a birthday cake. I think that’d be cute.

And giving a big middle finger to all of the advertisers and haters that took your other two covers away.

Claire Sinclair: Yeah, definitely. There could even be one of those dialogue bubbles that says, “Look, I’m 21 now—now what?” [Laughs.] Hopefully I can get on the cover next year. Fingers crossed.

Well, I’d think that holding the Playmate of the Year title is a pretty solid consolation prize for losing out on covers, no?

Claire SinclairLaughsvery

Was it difficult to get your foot in the door, so to speak, and become a Playmate last year? Just two years ago, you were a high school student, and now you’re Playmate of the Year—it seems like it’s all happened really fast for you.

Claire SinclairPlayboy

Yeah, the old Chinese Theater. I saw Batman get into a shoving match with Charlie Chaplin there once.

Claire SinclairLaughsBeauty And The Beast

The Bunny House

Those days in costume outside the Chinese Theater must’ve been surreal. There are some nutty people walking around that area.

Claire Sinclair

Can anyone just show up there in a costume and join the crowd, or is there some kind of initiation you have to go through?

Claire SinclairLaughs

Did you just take a shot in the dark and show up as Belle, or did you scope the scene out first?

Claire SinclairLaughshated

How has your life changed from all of that since the Playmate of the Year announcement?

Claire SinclairTwilight


You’ve made no mystery about the fact that Bettie Page is your idol, and she was known for her pin-ups and burlesque shows, so that must be really cool for you to channel some of that Page-ness on stage. Where does your fascination with Bettie Page and the old pin-up culture come from?

Claire Sinclair

You seem to be at the forefront of a pin-up resurgence. Why do you think the look and feel of those vintage pin-ups aren’t all that prevalent today?

Claire Sinclair

As far as the burlesque show you’re working on, is it going to be anything like that Christina Aguilera movie, Burlesque? Hopefully not, because that movie sucked.

Claire SinclairLaughs

Is being a Playmate of the Year a 24/7, seven-days-a-week job?

Claire Sinclairhave

Last year’s winner, Hope Dworaczyk, was a cast member on the most recent season of Celebrity Apprentice. Are you looking for gigs in that vein?

Claire SinclairDancing With The StarsLaughsLaughs

We’d vote for you, no question. Switching gears a bit, in your Playboy profile, you mention that the kinds of guys that you find are sexy are “man-boys.” We’re not sure if that’s a positive or negative description.

Claire SinclairLaughs

That actually plays into your willingness to dress as a Disney character in public, too. Would your heart melt if a boy-ish-looking guy showed up for a first date in a Spongebob Squarepants costume?

Claire SinclairLaughs

So, for instance, a guy whose idea of a great date night would be to buy you a ticket to see X-Men: First Class with him and school you on all of the mutants’ back-stories? Because I could totally do that.

Claire SinclairLaughs

These days, you must be receiving tons of outspoken attention from guys everywhere. Is that something you’re comfortable with?

Claire SinclairLaughs

The older men, in particular, could be gravitating toward you due to your whole old school pin-up vibe.

Claire Sinclair

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