She was never Josie Grossie! Drew Barrymore stole hearts from the second she hit the big screen in Never Been Kissed.

The actress played Josie Geller in the 1999 romantic comedy. The aspiring writer posed as a high school student to study teen culture, but things got complicated when the never-been-kissed (hence the title) twentysomething fell for her teacher Sam Coulson (Michael Vartan).

The film had a star-studded cast that included David Arquette (Rob Geller), Molly Shannon (Anita), John C. Reilly (Augustus “Gus” Strauss), Leelee Sobieski (Aldys) and Garry Marshall (Rigfort). Jessica Alba, Octavia Spencer and James Franco also played supporting roles before hitting the big time.

The stars reunited in September 2021 to revisit the movie’s best moments. “There’s a story about the famous scene that very few people know about,” Vartan explained on The Drew Barrymore Show at the time. “I get up to the mound, we embrace and we start kissing, and you really kissed me. I mean, you really kissed me. I was not ready for it in the least and I am a man. I was a very young man back then, and I had feelings.”

The Alias alum added: “The feelings were — they just happened — and I very quickly realized I was in a very bad spot because I was wearing very loose, like, slacks, and I thought, ‘This is going to be a disaster when they cut, I must preemptively end this.’”