Why Natasha Lyonne Was American Pie's Best Character

Twenty years ago, American Pie premiered, and its impact was soon felt. Tara Reid and Seann William Scott became stars, “MILF” entered the lexicon, and teenage flute players started making “this one time at band camp” jokes. Today, Rotten Tomatoes credits it with “bringing back the teen movie genre.”

I grew up hearing plenty of American Pie references (I was in marching band, so those band camp jokes were inescapable), but I never watched the movie until this past weekend. My parents were pretty strict about keeping me away from R-rated movies when I was growing up, and by the time I was 17, I had plenty of Judd Apatow-produced comedies to watch instead of the ‘90s classics. I was curious to watch American Pie from the perspective of an adult in 2019 — knowing that its basic premise is about a group of boys who make a pact to lose their virginity before graduation... I wasn’t expecting much.

For the most part, American Pie was exactly what I thought it would be — sexist, dated, and with some ideas about consent that definitely do not stand up. You might have heard some variation of the saying “he treats women like a vending machines, putting kindness coins in and expecting sex to fall out”? That’s all I could think of while watching this movie. The male characters treat sex as something they’re entitled to — something women "owe" them, but don't actually enjoy themselves.

One scene is particularly cringey: when Nadia (Shannon Elizabeth) informs Jim (Jason Biggs) she needs to change clothes after their study session, he offers her his bedroom — where he sets up a hidden webcam so he and his friends can watch her change. Turns out that Jim made a mistake and sent the streaming link to more people than he intended, so when Nadia decides to take a break and masturbate before changing, hundreds of people are watching without her knowledge or consent. Sure, American Pie is only a teen comedy, but teen comedies contribute to our cultural understanding of sex. Look at how widespread the term “MILF” is now, thanks in large part to American Pie. By the way, the MILF storyline — in which dorky high school student Finch (Eddie Kaye Thomas) has sex with his friend’s hot mom (Jennifer Coolidge) — is pretty troubling, too, because of the inherent power imbalance between an adult and a teenager. While Finch might be legally an adult, he has a lot of growing up to do.

But there’s one character in this movie that offers a different point of view: Jessica, played by a baby-faced Natasha Lyonne. Rocking bucket hats and butterfly chokers, Jessica is best friends with Vicky (Tara Reid) but is something of a loner herself. She’s already had sex, so her peers look to her for advice. She’s blunt: The first time we see her, she’s telling Vicky that she doubts Vicky and Kevin (Thomas Ian Nichoals) will be able to make a long-distance relationship work after graduating. But she tells it like it is. After Vicky says she wants to wait to have sex until everything is “completely perfect,” Jessica responds, “It’s not a space shuttle launch, it’s sex.”

Jessica’s best advice comes after Vicky gives Kevin a blowjob at a party. “Kevin likes it,” Vicky tells her. “He likes getting head. Gee, what a total shocker,” Jessica says. She then asks Vicky if she's ever had an orgasm. When Vicky confesses, “I’ve had one… I think,” Jessica responds, “No wonder you’re not psyched about sex.” She then asks Vicky if she’s ever masturbated — or, as she puts it, “You’ve never double-clicked your mouse?” While this is an incredibly ‘90s way to put it, her advice is spot-on: masturbation can help you get comfortable orgasming, both alone and with a partner.

At the party, Kevin complains to his friends that Vicky “only” gave him a blowjob instead of having P-in-V sex. Vicky overhears and asks Jessica to take her home – which she does. Later, Jessica tells Kevin how he can win Vicky back: he needs to tell her he loves her ("that's how I was duped"), or he needs to make her come. “Look, kid, it’s up to you,” she says. “The big L or the big O.” This advice, combined with a secret “Bible” of sex tips, leads to Kevin going down on Vicky for the first time — and Vicky finally has her first orgasm.

At the end of the movie, we see another character who shares Jessica’s belief that sex should be enjoyable for everyone: band geek Michelle (Alyson Hannigan). After prom, Michelle suddenly tells Jim that she masturbates and that she decided to go to prom with him because she wants to have sex and thought he’d be "a sure thing." She puts Jessica’s words into action, but it’s Jessica who pops up throughout the movie to share some straight-talking, sex-positive wisdom: female masturbation is healthy, sex should feel good for everyone involved, and yes, you’re probably going to break up with your high school boyfriend.