The Cast of Never Been Kissed (1999)

Credit: @drewbarrymore

The story of Josie Geller was brought to our attention in 1999. Played by the lovely Drew Barrymore, Josie Geller is a character in her mid-20s who has never been kissed. The movie is also titled, aptly so, Never Been Kissed. The story revolves around the young woman and her lack of romantic experience. She is a writer, and her editor wants her to pose as a high school student who is learning as much as she can about the lives of teenagers while pretending to be one. Of course, drama ensues. She was always a dork, she is not comfortable around kids, and she falls head over heels for a teacher – but he thinks she’s a student and it’s inappropriate, so he doesn’t do anything about it. It all unravels in the end, but fans want to know more about the cast of Never Been Kissed.

Drew Barrymore

She’s one of the most famous actresses in Hollywood. Since her role as Josie Geller, she’s done so much. She’s a child star, an Adam Sandler movie favorite, and even has her own talk show now. She is a woman beloved by many.

David Arquette

He plays Drew Barrymore’s character’s brother in the movie Rob Geller. He’s also the star of the Scream movies. He married and divorced Courtney Cox and continues to parent their daughter and work regularly. He also has a production company of his own.

Credit: @drewbarrymore

Michael Vartan

He’s a talented actor who went on to star in hit shows such as Alias, movies such as Monster-in-Law, and more. He’s always working. He plays the teacher Drew Barrymore’s character falls in love with during the movie. He’s always the guy that everyone falls in love with.

Leelee Sobieski

She’s a fellow high school nerd who decides to befriend the new girl, played by Drew Barrymore. For a long time, in the 90s and very early 2000s, Sobieski was the star of many movies. She was in Deep Impact, Glass House, and more. However, she chose to retire in 2012, and no one knows what she is up to these days. We imagine she’s simply living her life as privately as possible, and she’s likely enjoying that.

Molly Shannon

Everyone’s favorite Saturday Night Live comic plays the role of Anita, another teacher at the school. Of course, we all know Molly Shannon continued her career as one of the most prolific comedians of our time, and she’s darn good at it. She’s everything a person wants to be while working in Hollywood.

Credit: @drewbarrymore

Jeremy Jordan

He played Guy, the most popular guy in school. He took Josie Geller to prom, they were voted king and queen, and things took a very bad turn from there. Jordan is not the most famous person from the cast, but he did continue working in Hollywood. He did some movies, tried his hand at a career as a music artist (it didn’t go well), and mostly fell off the map in the mid-2010s.

John C. Reilly

He’s Josie Geller’s editor and the one who wanted her to pretend to be a high school student undercover. But, of course, he’s already one of the most famous actors in the world, and this movie was just another in a long list of successful movies for him. He’s been in every movie imaginable.

Other Famous Faces in the Cast of Never Been Kissed

Just when you thought you’d seen it all – and you have seen all the major characters in this film – you realize you forgot about the other major actresses and actors. They did not all have large roles in this movie, but they had massive careers. For example, did you know Octavia Spencer had a small role in the film? What about Jessica Alba and James Franco? They both appeared. Jessica Alba plays one of the popular girls at school. She’s beautiful and not very nice in this role, but it works for her. She does it well.

The Cast of Never Been Kissed Worked Well

This is a movie that works. It’s a traditional romantic comedy that leaves us all feeling good at the end. Sure, it touches on a few things that far exceed the world of appropriate – like a teacher developing feelings for a student even though he doesn’t act on them in any capacity. However, it works. The cast of Never Been Kissed is considered an ensemble cast now. But, then, they weren’t nearly as famous – some were, but others were not. It’s a great cast, a great movie, and something absolutely worth watching again.