Natasha Lyonne is no one's ingénue. Got that? In interview after interview, she straddles the fence between smart and smart-aleck, using her Manhattan, N.Y., moxie and personal charm to pull it off. It's that same charm that shines through as she depicts everyone from a sexually savvy student in American Pie to Woody Allen's daughter in Everyone Says I Love You, knocking the socks off audience members in cineplexes and dinky art-house theaters alike. Not to mention the fact that she's got a swarm of brassy curls that deserves a separate billing of its own.

Lyonne and her older brother, Adam, grew up in New York City, the children of race car driver Aaron Braunstein and Yvette Lyonne, a product licensing consultant and former ballerina. The youngest Braunstein's interest in acting was perhaps piqued during a subway ride in the early '80s. Lyonne told Seventeen that she was reading aloud from the Wall Street Journal, and that her fellow commuters were quite taken with her impromptu performance. "They started laughing, and then I stood up on my seat and kept reading," she said. Thus, a star was born.

Lyonne began professionally entertaining the masses in 1986, playing Opal on the television series Pee-wee's Playhouse and garnering an uncredited role in the Meryl Streep vehicle Heartburn. However, Lyonne's personal life dictated that when audiences saw her next, she'd be a burgeoning teenager. She explains in Los Angeles magazine, "My parents were about to get divorced, and as a last attempt they decided to salvage the marriage by moving to Israel for the sake of the children. It's as though Terry Gilliam moved into their consciousness for five minutes, and the next thing I knew, we were in Israel and my father was a boxing promoter."

The last-ditch effort failed, and Lyonne and her mother returned to Manhattan, allowing the former to add As the World Turns and Dennis the Menace to her credits, and, according to Lyonne, to "[go] through my pitiful yeshiva puberty years." The pair relocated to Miami, where Lyonne reluctantly attended a posh private religious school.

Unexpected salvation came in the form of bespectacled director Woody Allen, who chose the then-16-year-old Lyonne to portray his daughter, D.J., in his first (and hopefully last) musical, Everyone Says I Love You, which also starred Edward Norton, Drew Barrymore,Julia Roberts, and Alan Alda. Lyonne wasn't about to refuse such an offer; however, her own inexperience may have tainted the opportunity.

"I didn't actually get much from that movie," she told Rough Cut. "There were so many movie stars in that movie, I was really intimidated by the whole thing. So, I probably didn't do as good a job as I could have as far as just being free in front of the camera and being myself, which I think was what he wanted. … But, to me, it was such a huge thing that someone like Woody Allen, who is obviously such a hero to me, would choose me for something … just to play his kid, you know?"

Everyone gave Lyonne's career a boost; it also helped secure her an early acceptance to New York University, with plans to study film and philosophy.

"When I applied to NYU, I did this essay, drawing some bridge between T.S. Eliot's Hollow Men and working with Woody Allen. For the life of me, I can't think of what bridge there was, but I'm sure it didn't hurt that I mentioned Woody's name in a personal context," Lyonne recalled in an interview with UniverCITY. "The next thing I knew, [NYU] said, 'Drop out of high school immediately, move to New York City, pursue your dreams as an actor and come to NYU and you'll finish your senior year credits.'"

Lyonne has since deferred enrollment three times. She joked, "The only way I get jobs is if I'm enrolled at NYU and about to write the tuition check; then Hollywood calls."

Hollywood dialed Lyonne's number twice in 1998, although the first call, for the extinct-on-arrival comedy Krippendorf's Tribe, was probably just a prank. In fact, possibly the only person who saw it was the Las Vegas card dealer who recognized an underage Lyonne just before passing her a hand (the skilled actress convinced him she was someone else and proceeded to win big).

Fortunately, the other call resulted in her casting as Vivian, the lead of director Tamara Jenkins' semi-autobiographical movie, Slums of Beverly Hills. Lyonne held her own against co-stars Alan Arkin, Marisa Tomei, and an impressive set of prosthetic breasts. In Slums, Vivian has to deal not only with her family's nomadic lifestyle, but also with a newly sprouted set of C-cups. Lyonne, whose own female assets are modest in comparison, took the resulting press in stride.

"I was the happiest girl in the world," she told People. "Here I was playing the chick I always wanted to be — and I didn't even have to get surgery."

Lyonne's performance in Slums secured her casting director quick-dial status; it also meant that the actress was officially bi-coastal. She explained to Los Angeles magazine that when she arrived in L.A., "I thought all the basic things. You know, 'What's up with the water bottles and the vapidity?' I was so deep and New York." A visit to her mom's place in Miami gave her perspective: "I realized that Miami is my heart, New York is my home, and Los Angeles is my office."

Lyonne's next picture, Modern Vampires, is noteworthy perhaps only for the kiss she shares with co-star Natasha Gregson Wagner. The movie had "straight to video" written all over it; however, Lyonne's future forays into cinematic lesbianism would be far more publicized.

In 1999, Lyonne appeared in American Pie, a Porky's for Generation Y. The 20-year-old relished her role as sexual peer counselor. "In American Pie, my character's the only non-virgin in a group of high schoolers," Lyonne explained to Mademoiselle. "She pops in and out, convincing people to have sex. That's why I get the big bucks, because I'm so damn good at that." (Lyonne returned for the summer 2001 sequel, American Pie 2.)

Next, Lyonne donned some stilettos and a god-awful fake fur jacket to bring KISS's "Christine Sixteen" to life in Detroit Rock City. Lyonne was the first actor to sign to the movie and was more or less hand-picked by the tongue king himself, Gene Simmons. Lyonne said in a Metal Edge interview, "[T]hey invited me down to Gene Simmons' strip club birthday party. … As soon as I walk in, Gene walks up to me and puts a baseball hat on my head and starts talking to me. Someone else walks up to him from Fox Searchlight, who says, 'Do you know Natasha Lyonne? She was in our movie.' And he goes, 'Of course I know Natasha Lyonne, she is in my movie.'"

Apart from her noteworthy friendship with Gene Simmons, Lyonne came away from Detroit with a real-life love match with co-star Edward Furlong. The couple broke up in summer 2000.

Lyonne next starred in the John Waters-esque comedy But I'm a Cheerleader, in which her straight-laced Megan is sent to a deprogramming camp for homosexual youth. While there, Megan falls for a baby butch lesbian, played by Clea DuVall (Girl, Interrupted). The young actress previously portrayed a lesbian activist in the 1999 HBO movie If These Walls Could Talk 2.

Lyonne also starred in and produced Freeway II: Confessions of a Trick Baby, the story of "a girl who's a bulimic convict … [who] escapes life in prison and goes on the run with her sidekick who's a sex offender. They both have life sentences. Her sidekick knows this nun in Mexico named Sister Gomez who turns out to be Vincent Gallo in drag. There are lots of bullets and it's like Hansel and Gretel but really [messed] up." And it's also out on video. Her name is attached to a slew of upcoming pics, among them The Auteur Theory, When Autumn Leaves, Rat Girl, Night at the Golden Eagle, and the Meg Ryan-Hugh Jackman romantic comedy Kate & Leopold..

As her fame grows, Lyonne's ego will doubtlessly remain a respectable size. When asked by New York magazine to explain her success versus that of other starlets, she replied, "I don't know that I'm better. I think it's just that I'm weirder."