When I’m 40, this is where I want to be, like, always,” says Analeigh Tipton, 23, as we enter the Moonlight Rollerway, just past the Gentlemen’s Club strip joint on a lonely stretch of road in Glendale, California. It’s eight o’clock on a Monday night, and the rink is already teeming with senior citizens and teenage girls. “If I’m doing this, or I’m in a disco club at 40, it must mean I’m in a good place in my life. This takes really happy, unique individuals.” Such as the older gentleman who shoots us with finger guns every time he skates past backward, dancing to “We Want the Funk.”
Outside these walls, Tipton is a promising young actress who finished in third place on America’s Next Top Model in 2008. Inside, though, she’s nobody compared with the man doing high-speed yoga moves on one skate or the trio line-dancing on wheels. “Oh, God, if they were doing the Electric Slide, I would be on that shit!” she says.
Tipton’s three memorable roles so far—as a babysitter who sends topless pictures to Steve Carell in Crazy, Stupid, Love, a pimp on HBO’s Hung, and a naïve co-ed tricked into “non-procreative lovemaking” in Whit Stillman’s Damsels in Distress (out this week)—have been linked by a theme: “Nakedness,” says Tipton, giggling. “Inappropriate!” But Tipton herself exudes a sweet, dorky innocence. She’s in that fleeting, guileless stage of pre-fame where the person she presents to the world seems to be largely who she is—a girl who actually frequents this charmingly low-rent roller rink down the street from her house and who arrived tonight wearing a cotton dress stained with dog slobber.
She was born in Minnesota, where, she says, “you ice-skate before you walk.” She started figure skating competitively at 8, eventually competing in two U.S. Junior Figure Skating Championships before growing too tall for the sport (she’s five-foot-nine) and retiring at 16.
Her growth spurt was just one in a series of setbacks on the way to an acting career. Every college she applied to rejected her. Worse, she thought she was going to USC film school, only to find on the eve of her congratulatory party that there’d been a mix-up with the acceptance letters. She eventually studied film at Marymount before dropping out to do America’s Next Top Model. “But not Loyola Marymount,” she says. Rather, “the one that they hide up in the hills of Palos Verdes that nobody talks about.”
She’s unlucky in love, too, recalling her first boyfriend, who cheated on her with another boy, and a disastrous OKCupid date at this very rink, back when she was still under-the-radar enough to go unrecognized by guys perusing her profile. “He said he didn’t want to go out with me again because I was too afraid to fall, and he doesn’t date ‘safe’ girls,” she says, laughing. “I was like, ‘I’ve skated for sixteen years. I don’t like to fall. I know how it feels!’ ” When she’s not skating or acting, she surfs and plays the live-action version of Dungeons & Dragons as an elf whose weapon of choice is a longbow. “That probably explains why I’m single. In so many ways.”
Her post-ANTM modeling career was brief and undistinguished. “I got some catalogues. Internet catalogues, not even [print] catalogues. It was bad.” Then Ford, her agency, dropped her. One problem was the hook-shaped scar on her right upper lip, the result of a collision with a playground swing when she was 3. “So many people in the fashion industry were like, ‘We’re so sorry that happened to your face.’ ”
“I hated modeling,” she continues. “I was terrible at it. I wanted to talk. I wanted to smile. ‘Don’t. You’re angry.’ Why am I angry? I’m in bright pink and I have a lollipop in my hand. And what am I doing wearing heels? Why am I riding a bull?” When she was kicked off ANTM, Tyra Banks told Tipton she should pursue acting. Her first break was a minuscule role as “Hot Chick” in last year’s The Green Hornet. “I remember calling my mom: ‘I got Hot Chick! I got Hot Chick!’ ” she says. The character was renamed Ana Lee when director Michel Gondry decided to include a bit in which Tipton corrects Seth Rogen on the pronunciation of her name (it’s Ah-na-lee), though her parents still refer to her as “our daughter, Hot Chick.”
But of her characters, Tipton most resembles Lily, the one she plays in Damsels. That’s partly because Stillman liked Tipton’s naturalism and kept most of her awkward mannerisms in the film. “She has a cute way of walking where, to punctuate a point, she goes up on her tippy-toes,” he says. Lily was supposed to be the movie’s villain, a transfer student to a third-tier East Coast college who is constantly undercutting Greta Gerwig’s Violet, a delusional optimist who believes that tap dancing can cure depression. But Tipton’s likability was undeniable. “The problem with Analeigh was that she brought such charm to the part I think she confused a lot of people about who the true heroine was,” says Stillman. “Some people feel very frustrated that Lily doesn’t win in the end.”
The rink is closing, and Tipton has to head home to tend to her dogs—an Australian shepherd named Tomahawk and an “adorable, dumb” cocker spaniel named Matilda—and rest up for her Damsels press day. (Next, she’ll play a college student saved from suicide in the dark comedy Buttwhistle, and a badass in the zombie romance Warm Bodies, from 50/50 director Jonathan Levine.) As we unlace, she tells the romantic tale of moving to New York for the first time to shoot Damsels. The airline permanently lost her luggage, containing her entire wardrobe, on the flight over. She rented an apartment under the Queensboro Bridge between a strip club and a preschool and only slept for three hours per night, after one closed and the other opened. “I didn’t know anybody and was so lonely, but I had a mouse friend, Dmitri,” she says. “It was really pathetic, but knowing there was a living thing with me made me so much happier. Until I realized that Dmitri also had Dominique. They shit in my bag under my bed so much. It still smells like mouse shit.” Still, she says, “It was perfect. I wouldn’t have had it any other way.”