Molly Gordon is a little intimidating in Booksmart. In the film—Olivia Wilde's directorial debut that opens in theaters next Friday—Gordon plays Annabelle (or "Triple A," as she's nicknamed for the so-rumored "roadside assistance" she provides her male classmates). Annabelle is the ultimate cool girl, all hoop earrings, micro gym shorts, and blasé attitude, which Gordon plays totally deadpan. Her delivery of lines like "I'm incredible at handjobs, but I got a 1560 on the SATs," will make you laugh, but also dredge up a few repressed high school memories. No wonder the 23-year-old features in two of the summer's biggest comedies.

Though Gordon was born in Los Angeles to parents in the industry (mom is a film producer, dad is a director) and knew that she always wanted to perform, Gordon largely put off pursuing a career until she was in college, where she briefly enrolled in New York University (as in, two weeks brief) before leaving to fully dive in. "I always knew I wanted to wait until I was done with high school—I feel like you only have that time," she explained. "This is a very difficult job, with the amount of rejection. That’s dark when you’re a kid. I would not have been able to do it."

Molly Gordon photographed by Maridelis Morales Rosado for W Magazine.

As a kid, she enrolled in a local theater group where she met her best friend Ben Platt—"We did like 50 shows by the time we were 10, playing every variation of a duo," she said. "He was my first kiss in a play."—but it wasn't until she was heading to New York that she sought out an agent and auditions. Ironically, the first big job she landed, a role on the drama series Animal Kingdom, led her back to L.A. soon after she'd left. "That was kind of my college experience," she said of the show. "But I lived at home. So it was me, my dad, and mom, and all of the younger kids who went to my high school. I’d see them at dinner with my parents. People were like, ‘You live with your parents?’ And I’m like, ‘I love this.’"

After starring on the series for three years, Gordon was then cast in what she describes as a "dream" role: Melissa McCarthy's daughter in the 2018 comedy Life of the Party—a film, ironically, set on a college campus. "That was the most fun thing I’ve ever done in my life,' Gordon said. "First of all, to be able to do a movie about being close to your mom and it was set in college? Melissa would always be like, ‘Is this what [college] is like?’ I was like, ‘I have no fucking idea,’ I really was just going with it." It also allowed Gordon to show her talent and natural inclination to comedy. "It was so surreal," she said. "Getting to improvise with [Melissa]... I’m just such a big fan of hers and improv. We would shoot it the way we wrote it, but then get to improv and play for hours. It was so fun. I couldn’t believe it was a job."

Molly Gordon photographed by Maridelis Morales Rosado for W Magazine.

This summer, Gordon has two comedies coming out, Booksmart and Good Boys, in August. "They both are comedies, but they played very differently." she said. "One is celebrating female friendship in high school, and one is celebrating middle school friendships of guys. It’s interesting to see the different dynamics."

In a bit of life imitating art, in Booksmart, Gordon stars opposite her real life best friend, Beanie Feldstein. "I read Booksmart a couple of years ago, so I always knew that it was this wonderful project," she said. "Then Beanie got cast and I just tried to do everything i could to be in this movie, work with Olivia, and be near Beanie in any way. I was like, ‘I’ll literally be a caterer.'"

Ironically, Gordon plays Feldstein's rival in the movie. "We think that because we are best friends, it’s easier to be mean, because we can say anything to each other at this point and it doesn’t matter," she said. "Beanie is just an extraordinary actress, and in this movie she and Kaitlyn [Dever] are so good together. I don’t know about you, but i haven’t seen a movie that treats a female friendship like a love story. Your first best friend really is your first love."

While Booksmart saw Gordon surrounded by her peers—in addition to Feldstein and Dever, the film stars fellow rising actresses Billie Lourd and Diana Silvers—in Good Boys she is one of the film's only adult actors, as well as one of the few women on set. The film, produced by Seth Rogen and Evan Goldberg, follows a group of 12-year-old boys, including Room's Jacob Tremblay, on a night gone very wrong. "They were so funny and amazing," Gordon said of her pre-teen co-stars. "It was definitely like, ‘I don’t want to have kids anytime soon, but i think you’re great.’ Jacob is like a 70-year-old man. He’s more mature than I am. One time he was just like, ‘Molly, so good today,’ and just walked away. So professional."

Despite the young actors (Tremblay is 12 himself), the film doesn't shy away from the risque tropes you might expect from a Rogen and Goldberg production; there promises F-bombs, drugs, and sex toys—and that's just the trailer. "It was so weird and wonderful," Gordon said. "The craziest thing was they would ask me, ‘Molly, what does this mean?’ And I would have to decide if I was going to be the one to tell them. I didn’t feel like I wanted ownership of that for the rest of my life."