“Never Been Kissed” Turns 25! See the Starry Cast Then and Now

Catch up with Drew Barrymore, David Arquette and more of the A-list cast as the movie marks a milestone

If Josie Grossie could see herself now.

Twenty-five years ago, Never Been Kissed hit theaters, bringing another memorable Drew Barrymore character to life. In the film, the 24-year-old actress played Josie Geller, a Chicago-based newspaper writer tasked with embedding herself in the trenches at a suburban high school — to mixed results.

"All we wanted to do was make something that felt like the way so many of us feel growing up," Barrymore wrote on Instagram on the film's 20th anniversary. "It’s raw and ridiculous, beautiful and helps you decide what is important and what isn’t ... Josie Grossie forever."

As the film hits 25 years since its release, catch up with the cast of Never Been Kissed, then and now.

Drew Barrymore as Josie Geller

Everyone knew Drew Barrymore by 1999 thanks to her famous family, child stardom and recent leading roles in Scream, The Wedding Singer and Ever After. But Never Been Kissed was also the first film Barrymore produced (with business partner Nancy Fallon) under her Flower Films, she revealed in her 20th anniversary tribute.

In the film she navigated Josie Geller's ups and downs, from reliving the trauma of her own "Josie Grossie" high school days to becoming prom queen and all the twists and turns between. "Humor and humility are linked like besties," she wrote in 2019. "And everyone feels vulnerability while they are figuring out who they are and what they stand for."

In the years since, Barrymore, now 49, hasn't stopped, notably starring in the Charlie's Angels franchise, plus Riding in Cars with Boys and rom-coms like 50 First Dates and Fever Pitch, in addition to hosting her eponymous Emmy-nominated daytime talk show and juggling off-screen production duties. She has two daughters with ex Will Kopelman.

Michael Vartan as Sam Coulson

Michael Vartan balanced his personal ethics with his pull to Josie as teacher Sam Coulson, who ultimately fell for Barrymore's character once her truth was revealed, giving her that first kiss.

"This movie's been a huge part of my life, every time I'm stopped it's always Never Been Kissed, so it's a pretty amazing thing to be a part of," Vartan told Barrymore on a 2021 episode of her talk show.

Prior to the film, Vartan had a handful of movies on his résumé, and famously moved on to a role in TV's Alias, followed by Big Shots, Hawthorne and most recently The Arrangement. The 55-year-old also starred opposite Jennifer Lopez and Jane Fonda in Monster-in-Law.

Jeremy Jordan as Guy Perkins

Jeremy Jordan was a musician first, releasing the hit "The Right Kind of Love" in 1993 before moving into acting soon after.

As popular heartthrob Guy Perkins, he took Josie to the prom, only to be a pawn in a plot against her friend Aldys.

Now 50, Jordan has mostly retreated from the spotlight since Never Been Kissed.

Leelee Sobieski as Aldys

A staple of late-'90s teen movies, Leelee Sobieski played Aldys, a member of the social group The Denominators who immediately warms to Josie. In the years prior, she'd starred in Charlie Grace, Deep Impact and Jungle 2 Jungle, moving on to films including Here on Earth, Joy Ride and the more adult Eyes Wide Shut.

In 2016, she spoke to Us Weekly about steeping back from the industry, saying, "I am just focused on my kids. I think that’s mainly why I stopped."

Sobieski, now 40, is working as an artist under her married name, Kimmel.

Jessica Alba as Kirsten

Never Been Kissed was Jessica Alba's very first feature film role. In it she played Kirsten, one of the school's popular girls who was out to get Josie.

"I had my 17th birthday on the set," Alba recalled in a 2020 chat with Barrymore. "It felt like camp. You really took so many people under your wing and guided them. A lot of us were just really starting out and you set the stage for us and gave us a platform to be successful, so thank you."

Alba moved on to the television series Dark Angel, plus a string of blockbusters including The Fantastic Four, Sin City and The Love Guru. The mom of three, now 42, focuses more on her off-screen work these days, running The Honest Company. She has been married to husband Cash Warren since 2008.

David Arquette as Rob Geller

David Arquette played Josie's brother Rob Geller, who returned to high school himself in hopes of helping his sister complete her story — and getting some glory along the way.

He actually grew up down the street from Barrymore, she shared on an episode of her talk show, giving the pair their own brother-sister vibes long before they hit the screen. "It was a dream come true," Arquette said of working with Barrymore. "You put this beautiful film together that was so heartfelt."

Arquette, also raised in a family of actors, began working in 1990 on The Outsiders, appearing in the Scream franchise and an endless stream of movies since. He's done extensive voice work — most notably on Disney's Jake and the Neverland Pirates — and in recent years has pivoted into wrestling, too.

Arquette, now 52, shares daughter Coco with ex Courteney Cox and has two children with wife Christina McLarty.

John C. Reilly as Gus

As Gus, John C. Reilly pushed Barrymore's Josie to embed herself with the popular kids — and watched it unfold via livecam.

Like many of his costars he'd been acting steadily prior to the film, in movies including Days of Thunder, Boogie Nights and The River Wild. Following Never Been Kissed, he went for the dramatic in Gangs of New York and Chicago, but has also brought endless laughs with Walk Hard, Step Brothers and Anchorman 2, in addition to voice work on films like Wreck-It Ralph and Sing.

An Oscar and Golden Globe Award nominee, the 58-year-old has been married since 1992 and has two grown children.

Molly Shannon as Anita

Molly Shannon was busy bringing the laughs on Saturday Night Live when she joined the cast as Josie's newspaper coworker, Anita.

In a 2014 chat with The Daily Beast, Shannon called the film "so funny," and sang the praises of her costar. "Drew was so great to work with. You know, she’s been in the movie business since she was a little kid but she was just great."

Shannon continued on SNL through 2001, moving into film with Wet Hot American Summer, the Scary Movie franchise, Bad Teacher and several films centered on SNL characters and costars. Most recently Shannon, now 59 and a three-time Emmy nominee, starred in the ensemble comedy The Other Two as a momager who launches a big career of her own. The actress has two children with her husband of 20 years.

Garry Marshall as Rigfort

Beloved rom-com director Garry Marshall picked up a part in the film as Josie's assigning editor, James Rigfort. His career before and after the movie was prolific, with directing credits on Pretty Woman and Runaway Bride to his name in addition to production work and acting roles in Murphy Brown, Hocus Pocus, Happy Days and A League of Their Own.

Marshall, a five-time Emmy nominee, died on July 19, 2016, at 81 years old. He was survived by his wife and three children.

The Rest of the Cast

A few other notable names had minor parts in the movie; Never Been Kissed marked James Franco's first feature film, with Marley Shelton, Jordan Ladd, Cory Hardrict, Octavia Spencer and Marissa Jaret Winokur playing small roles, too.

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