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Some performances are acting. Others are confession. Drew Barrymore has said that her turn as Josie Geller in Never Been Kissed belongs to the second category — a role she didn’t so much play as relive. The film’s most painful beat, she’s acknowledged, was pulled straight from the worst memory of her own adolescence.

Drew Barrymore and Marley Shelton hit the Hollywood premiere of Never Been Kissed on March 30, 1999. Photo by Dan Callister / Hulton Archive via Getty Images.

The egging scene is the giveaway. In Never Been Kissed, Josie Geller waits on her porch in her prom dress while her date, Billy Prince, pulls up in a limo with another girl and pelts her with eggs. Barrymore said that kind of pain was partly her own.

Drew Barrymore and then-fiancé Tom Green share a kiss at the Charlie’s Angels premiere in Hollywood on October 22, 2000. Photo by Chris Weeks / Hulton Archive via Getty Images.

Barrymore’s real experience at Cal Prep School in Stoneridge, California, involved a cheerleading practice. As a teenager, she described herself as overweight and awkward, with braces and skin “like a connect-the-dots game.” She was “always dying to be a cheerleader,” she said, so she accepted an invitation from a cheerleader, unaware it was a trick meant to let the popular girls watch the “school dork” struggle.

Drew Barrymore in a scene from the 1999 film Never Been Kissed. Photo by Getty Images.

Barrymore recalled that the most popular girl stopped mid-cheer when “fat little me” entered the gym. “What is she doing here?” the girl screamed, then, “Get that idiot out of here!” Barrymore ran out crying and eventually dropped out of school.

In May 1999, Barrymore said, “It is still the most humiliating moment of my entire life. I will never forget it.” She connected those memories to her role: “There are fears I truly still embody from high school – about not fitting in, about everyone hating me – that I really get to live through Josie.” The film’s egging scene draws on that sense of rejection rather than reenacting the cheerleading incident.

Drew Barrymore joins co-stars Leelee Sobieski, David Arquette, and Marley Shelton at the Hollywood premiere of Never Been Kissed on March 30, 1999. Photo by Dan Callister / Hulton Archive via Getty Images.

The awkwardness went back further than high school. Barrymore recalled fixating on her double chin, body and hair in grade school, seeing herself as “a total Josie Grossy.” “I was just devastated because I really wanted to try to make people happy and they didn’t want me around,” she said. That emotion, she explained, was the reason she made the film: “It taps into an emotion that everyone can identify with, the awkward moments of our high school years.”

Drew Barrymore at Zuma Beach in Malibu, caught mid-change on the sand in September 1996. Photo by Ramey Photo / MEGA.

The high-school set revived all of it. Barrymore said it gave her “immediate butterflies and ulcers” and the old pressure “to fit in… to be wearing the right clothes and have the right body type” — pressures she compared with Hollywood. Never Been Kissed was also the first film from her company Flower Films, and she said she was “very stressed,” with a “clenched stomach” throughout production because she feared she wouldn’t get another chance.

Drew Barrymore poses alongside wild animals at a Planet Hollywood event in Los Angeles to promote a celebrity T-shirt benefiting a wildlife rescue organization, February 1998. Photo by Ramey Photo / MEGA.

The film opened in theaters on April 9, 1999, and grossed $84.6 million worldwide on a $25 million budget. Recalling the shoot in 2024, Barrymore said the studio called to tell her she was “looking too unattractive.” Her answer was “good,” but, by her account, the studio thought the look went “too far” and feared she would “lose the heart because you’re going so far for the comedy.” She toned it down: “So Josie, what you see there is me dialed back.”

Drew Barrymore poses alongside Lucy Liu and Cameron Diaz at the Chinese Theater in Los Angeles for the Charlie’s Angels premiere in October 2000. Photo by Kevin Winter / Getty Images.

Barrymore has returned to Josie in talk-show and social-media appearances, including turns in the prom dress and braces. She’s described the character as an enduring part of herself: “I am still Josie Grossie. I always have been and always will be.”

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