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The Never Been Kissed Cast: 12 Shocking Updates And Where They Are Now In 2025

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Few romantic comedies capture the angst and awkwardness of high school quite like Never Been Kissed. Released in 1999, the film turned Drew Barrymore's production company, Flower Films, into a powerhouse and solidified its place as a quintessential late '90s classic. Now, as of December 2025, the film is celebrating its 25th-plus anniversary, which has brought a flurry of new updates, behind-the-scenes confessions, and cast reunions that fans are obsessing over.

Following the journey of 25-year-old copy editor Josie Geller, who goes undercover at her old high school to write a story, the movie is a beloved tale of second chances, self-acceptance, and, of course, a grand, public first kiss. The stellar ensemble cast, a mix of established comedic veterans and rising stars, have all gone on to achieve massive success, though some have taken surprising turns. Here is a comprehensive look at the main cast of Never Been Kissed and their most recent, up-to-date projects.

The Core Cast: Then and Their 2025 Status

The success of Never Been Kissed rests on the shoulders of its talented ensemble, many of whom were just starting their careers or were already household names from the world of sketch comedy. We break down the stars, their iconic roles, and their latest endeavors.

  • Drew Barrymore (Josie Geller / Josie Grossie): Executive Producer and Star. The film's protagonist, a nerdy copy editor who relives high school to write an expose.
  • Michael Vartan (Sam Coulson): The handsome, literature-loving English teacher who falls for Josie, unaware of her true identity.
  • David Arquette (Rob Geller): Josie's younger brother, a charismatic former high school rebel who helps her navigate the social scene.
  • Leelee Sobieski (Aldys Martin): The kind-hearted, intelligent outcast who immediately befriends Josie.
  • Molly Shannon (Anita Olesky): Josie's enthusiastic coworker and former classmate who aids her mission.
  • John C. Reilly (Gus): Josie's abrasive and eccentric newspaper editor.
  • Jessica Alba (Kirsten Liosis): One of the 'popular' girls who bullies Josie. This was one of her very first feature film roles.
  • James Franco (Jason Way): A high school jock and one of the popular kids. This was his film debut.

Drew Barrymore (Josie Geller): From Movie Star to Talk Show Host

Drew Barrymore was already Hollywood royalty when she produced and starred in Never Been Kissed, but the film cemented her transition into a powerful producer. Today, her career is centered around her highly successful daytime program, The Drew Barrymore Show.

The show has become a hub for Never Been Kissed nostalgia, hosting multiple cast reunions, including Michael Vartan, David Arquette, and Molly Shannon, to the delight of fans.

The Reboot Buzz: In a recent update, Barrymore has confirmed she is "totally down" for a Never Been Kissed reboot, expressing a willingness to revisit the character of Josie Geller. This news has sparked significant excitement among fans, who are eager to see a modern take on the classic story.

Iconic Revival: She also delighted fans by reprising her iconic "Josie Grossie" look, complete with braces and the memorable white feathered outfit, for a segment at the MTV Awards, proving her love for the character is as strong as ever.

Michael Vartan (Sam Coulson): The Awkward Kiss Confession

Michael Vartan, who played the dreamy English teacher Sam Coulson, has remained active in film and television, with notable roles in the series Alias and Bates Motel. However, it was his appearance on The Drew Barrymore Show that provided the juiciest, most current trivia about the film.

The Famous Kissing Scene: Vartan confessed to Barrymore that he was so overwhelmed by their famous baseball field kiss—which Drew made "really real"—that he had to fake an injury to excuse himself. He admitted he was "not ready" for the intensity of her on-screen passion, a delightful and candid tidbit that has recently gone viral among fans.

The Supporting Cast: Surprising Career Paths and Latest Projects

The film was a launching pad for several future A-listers and a showcase for established comedic talent. Their paths since the 1999 release have been incredibly varied, from stepping away from the limelight to winning major awards.

Leelee Sobieski (Aldys Martin): From Actress to Fine Artist

Leelee Sobieski, who played the sweet and insightful Aldys, a member of the social group "The Denominators," was a staple of late '90s teen movies. However, in a major life and career shift, Sobieski has largely stepped away from acting.

Current Focus: She now focuses on her career as a fine artist and sculptor, exhibiting her work in galleries. This move represents a complete departure from her early fame, making her one of the most surprising "where are they now" stories from the cast.

Jessica Alba (Kirsten Liosis): Hollywood Star to Business Mogul

Jessica Alba’s role as the mean girl Kirsten was one of her first feature film appearances. Following Never Been Kissed, Alba rose to prominence with roles in Dark Angel and Fantastic Four.

Current Endeavors: Her focus today is largely on her billion-dollar consumer goods company, The Honest Company, which she founded in 2011. While she still takes on acting projects, her entrepreneurial success is the primary focus of her current career, positioning her as a major business mogul in 2025.

Molly Shannon (Anita Olesky) and John C. Reilly (Gus)

Both Molly Shannon and John C. Reilly were already recognizable faces when they joined the cast. Shannon was a popular cast member on Saturday Night Live (SNL), and her character, Anita Olesky, was a comedic highlight.

Molly Shannon's Success: Shannon has continued her successful career in both comedy and drama, recently signing a first-look deal with HBO Max, demonstrating her continued relevance in the industry. She also reunited with her co-stars on The Drew Barrymore Show in a highly publicized event.

John C. Reilly's Diverse Career: Reilly, who played Josie's editor Gus, has since become one of Hollywood's most respected and versatile actors, successfully navigating between critically acclaimed dramas like Gangs of New York and hit comedies like Step Brothers and Wreck-It Ralph. His career post-Never Been Kissed has been one of consistent, A-list success.

The Future Stars: James Franco and Cory Hardrict

The film also served as the debut for two actors who would go on to have significant careers: James Franco and Cory Hardrict.

James Franco (Jason Way): His small role as a popular jock was his very first feature film. He quickly followed this up with his breakthrough role on the cult TV series Freaks and Geeks, which launched his extensive and varied career as an actor, director, and writer.

Cory Hardrict (The Denominators Member): Hardrict also made his film acting debut in Never Been Kissed. He has since built a solid career in both film and television, appearing in major projects like American Sniper and the TV series The Oath.

never been kissed cast
never been kissed cast

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