By Morgan Klosterman
5:31 PM PDT, April 9, 2024
Never Been Kissed was released in 1999 and ET is celebrating the 25-year anniversary of the movie! Take a look at the stars then and now!
In the beloved rom-com, Drew Barrymore plays Josie Geller, a.k.a. Josie Grossy, a newspaper reporter who returns to high school and poses as a student as part of research for a story. The movie also stars David Arquette, Molly Shannon, John C. Reilly and Michael Vartan.
Drew Barrymore
![Drew Barrymore](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2024-04/mk-Drew-Barrymore-1280-X-720-HERO-2-SPLIT.jpg?width=1024&quality=80)
Barrymore plays Josie Geller, a journalist who goes undercover as a high school student to get a juicy story for her newspaper. Her high school days were not so great, so fitting in as a high school student might be harder than it looks.
David Arquette
![David Arquette](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2024-04/mk-David-Arquette-1280-X-720-HERO-2-SPLIT.jpg?width=1024&quality=80)
Arquette plays Rob Geller, Josie's brother who was a popular baseball player in the prime of his high school years and turned into a nobody once he graduated. Similar to Josie, Rob also pretends to be a high school student to relive his glory days.
Molly Shannon
![Molly Shannon](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2024-04/mk-molly-shannon-1280-X-720-HERO-2-SPLIT.jpg?width=1024&quality=80)
Shannon plays Anita, Josie's co-worker. Anita is down for the journey of Josie going back to school and enjoys the ups and downs along the way.
John C. Reilly
![John C. Reilly](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2024-04/mk-John-C.-Reilly-1280-X-720-HERO-2-SPLIT.jpg?width=1024&quality=80)
Reilly plays Gus, the head of the newspaper, Josie's boss. He is skeptical of her new assignment so he watches her every move along her new journey.
Leelee Sobieski
![Leelee Sobieski](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2024-04/mk-Leelee-Sobieski--1280-X-720-HERO-2-SPLIT.jpg?width=1024&quality=80)
Sobieski plays Aldys, the first person to befriend Josie at her new school. She plays a brainy student that is not in with the "it" crowd. As a result, Josie has to distance herself from her in order to infiltrate the popular crowd and get a better story.
Sean Whalen
![Sean Whalen](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2024-04/mk-Sean-Whalen-1280-X-720-HERO-2-SPLIT.jpg?width=1024&quality=80)
Whalen plays Merkin, the inadequate assistant to Josie at the newspaper firm. Any chance he has to slack off or not do his job, he does.
Michael Vartan
![Michael Vartan](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2024-04/mk-Michael-Vartan-1280-X-720-HERO-2-SPLIT.jpg?width=1024&quality=80)
Vartan plays Sam Coulson, a high school English teacher that Josie develops a crush on.
Jessica Alba
![Jessica Alba](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2024-04/mk-Jessica-Alba-1280-X-720-HERO-2-SPLIT.jpg?width=1024&quality=80)
Alba plays Kirsten, head of the popular crowd. She makes life hard on Josie when she arrives to her new high school.
Marley Shelton
![Marley Shelton](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2024-04/mk-Marley-Shelton-1280-X-720-HERO-2-SPLIT.jpg?width=1024&quality=80)
Shelton plays Kristin, a popular girl at Josie's new high school. Josie has to pretend to be friends with for the sake of her job.
James Franco
![James Franco](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2024-04/MK-James-Franco-1280-X-720-HERO-2-SPLIT.jpg?width=1024&quality=80)
Franco plays Jason, a popular guy at Josie's new high school and Kirsten's boyfriend.
Octavia Spencer
![Octavia Spencer](https://www.etonline.com/sites/default/files/styles/640xh/public/images/2024-04/mk-Octavia-Spencer-1280-X-720-HERO-2-SPLIT.jpg?width=1024&quality=80)
Spencer plays Josie's co-worker at the newspaper firm. She watches Josie's journey while she is on assignment.