It's been 20 years since Josie "Grossy" Geller finally got in with the cool kids of South Glen South High School.
Desperate to publish an important piece of news and appease her editor-in-chief, Josie Geller undergoes her own undercover investigation of a place many are reluctant to revisit: high school.
It's been nearly 20 years since director Raja Gosnell brought the story of the self-conscious and romantically inexperienced copy editor of The Chicago Sun-Times to the big screen. In that time, the film's cast has had many successes in their careers in a wide variety of roles: Some of the rom-com's stars went on to win Oscars, and some went on to play bloodthirsty real estate agents.
Never Been Kissed grossed nearly double its production budget, raking in more than $98.6 million domestically (adjusted for inflation) after first hitting theaters April 9, 1999. The film went on to receive recognition from a number of awards shows, including the Teen Choice Awards and the MTV Movie Awards.
To celebrate the film's 20th anniversary,The Hollywood Reporter looks at what the original cast has been doing since the '90s.
From undercover newspaper reporter to secret agent to zombie businesswoman, Drew Barrymore has continued to play strong women who have needed to keep their identities a secret. But that's just a small sampling of her credits since Never Been Kissed.
In 2000, Barrymore played one-third of the dynamic all-female spy group known as Charlie's Angels. As Dylan Sanders, Barrymore worked alongside Cameron Diaz and Lucy Liu in McG's film adaptation of the late-'70s series.
Soon after, Barrymore started taking on more roles in Adam Sandler-led projects, ranging from 50 First Dates to Blended. It wasn't the first time she worked with the comedian, as she also played his love interest in 1998's The Wedding Singer.
Music and Lyrics, Beverly Hills Chihuahua, Grey Gardens and many other film and television projects later, Barrymore is now the living, breathing and man-eating real estate agent of the Santa Clarita Valley in Netflix's Santa Clarita Diet.
Over the years, Barrymore has acquired producing credits for a number of titles. The actress is also working on The Stand-In, a 2019 comedy that follows an actress and her stand-in constantly trading places in the workplace.
Drew Barrymore wasn't the only Never Been Kissed castmember to play a spy after the 1999 film.
Nearly five years after playing Barrymore's love interest in Never Been Kissed, Vartan secured a regular role as Agent Michael Vaughn on ABC's Alias. Varton starred as the love interest of Jennifer Garner's Agent Sydney Bristow.
Since 1999, Vartan has worked with other notable stars, like Jane Fonda and Jennifer Lopez in Monster-in-Law, where he played Lopez's husband-to-be.
Vartan also continued to venture into even more TV series. In addition to Alias, he starred as James Walker on ABC's Big Shots and A&E's Bates Motel. He is currently working on CBS' God Friended Me, a show about an atheist rethinking his relationship with religion after God adds him as a Facebook friend.
After The Outsiders, Buffy the Vampire Slayer, the first two movies of the Scream series and many other titles, landing lead roles was nothing new to David Arquette. In Never Been Kissed, Arquette played Josie Geller's older, goofier brother, Rob.
Since the 1999 rom-com, Arquette has gained both acting and producing credits for a number of TV series, including Cougar Town and Truck'd Up.
Like other Never Been Kissed co-stars, LeeLee Sobieski also earned more acting credits in a wide variety of titles after the 1999 romantic comedy. From South Glen South High's prom queen to a neo-pagan, here's what Sobieski has been up to.
In 1999, Sobieski became the title character of Joan of Arc, which follows the historical figure who led the French against invading English forces. Two years later, she starred alongside Stellan Skarsgard in the thriller The Glass House.
She also acted in titles like The Elder Son, Night Train and The Wicker Man during the early 2000s. The actress' most recent credit is for Amerikali Kiz, a Turkish TV movie that aired in 2018.
After the 1999 film, Molly Shannon went back to comedy and secured roles in numerous films. In Never Been Kissed, Shannon played Anita, one of Josie's Chicago Sun-Times colleagues.
Shannon added credits from shows such as Pushing Daisies, American Dad!, Glee and more to her résumé. The actress also reprised her role as Val Bassett from Will & Grace when the sitcom returned to TV in 2017, earning her an Emmy nom for best guest actress in a comedy series.
Most recently, Shannon starred as Cynthia Grimes in the Oscar-nominated film Private Life and stars opposite Sarah Jessica Parker and Thomas Haden Church in HBO's Divorce. She even played a part in Katy Perry's music video for Swish Swish.
From playing a staffer at The Chicago Sun-Times to portraying a mathematician and computing supervisor at NASA, Octavia Spencer has added scores of acting credits to her roster since the 1999 rom-com hit theaters.
In the same year as the Barrymore-led movie was released, and for more years to follow, Spencer continued to play background roles in a number of titles, including Spider Man, Legally Blonde 2: Red, White & Blonde and The X-Files. She then became a regular on ABC's Ugly Betty as Constance Grady, a U.S. Citizenship and Immigration Services case worker.
In 2011, Spencer played the snarky Minny Jackson of The Help, the caretaker responsible for the film's infamous chocolate pie. The performance gained Spencer not only her first Oscar nomination, but also her first Oscar win. After two years, Spencer also starred in Ryan Coogler's Fruitvale Station, which recounts the true story of Oscar Grant's accidental death at the hands of a San Francisco policeman.
Within the past year, Spencer produced the controversial 2019 best picture Oscar winner: Green Book. This year, Spencer will also lead the thriller Ma, in which the actress portrays a lonely woman who wreaks havoc and terror on a group of teenagers.
In Never Been Kissed, John C. Reilly played Gus, Josie's direct editor who suggested she work undercover. Since then, he's taken on a wide variety of roles ranging from Wreck-It Ralph to Chicago's Amos Hart, aka Mr. Cellophane.
The Oscar nominee recently received a Golden Globe nod for his performance as comedian Oliver Hardy in Stan & Ollie. Reilly also appeared opposite frequent collaborator Will Ferrell in Holmes & Watson and is in preproduction for Moonbase 8, a TV series about subpar astronauts hoping to get to the moon.
Since his days playing the Chicago Sun-Times editor-in-chief, Garry Marshall continued to build his acting résumé with features in a number of TV series like Monk, Brothers & Sisters and more.
Before his death in July 2016, the Happy Days creator also wrote for one episode of See Dad Run and wrote and directed Mother's Day, which starred Jennifer Aniston, Kate Hudson, Julia Roberts and more.
Marshall, who also directed Pretty Woman, died July 19, 2016, following complications of pneumonia following a stroke at 81 years old.
This Franco brother might have had a minor role in Never Been Kissed, but he too rose even further to stardom after the romantic comedy.
James Franco played Jason, one of Josie Geller's popular and rowdy classmates at South Glen South High. In the movie, Franco was always seen tagging along behind others, but never front and center of the film's popular group.
The same year as Gosnell's feature film, Franco starred as Daniel Desario in Freaks and Geeks. The role helped kick-start Franco's career, which includes credits in The X-Files, The Wicker Man and Spider Man, where he played Harry Osborn.
In 2011, Franco earned his first and only Oscar nomination to date for 127 Hours, where he portrayed Aron Ralston, a climber who faced tough decisions following a false rock-climbing move.
Within the past year, Franco has worked on a wide array of projects, including the Coen brothers' The Ballad of Buster Scruggs, The Disaster Artist, which he directed, and TV series The Deuce.
After Franco won a Golden Globe for Disaster Artist in January 2018, three actresses tweeted accusations of sexual misconduct. Addressing the accusations on The Late Show, he told host Stephen Colbert that "things that I heard were on Twitter are not accurate, but I completely support people coming out and being able to have a voice."
The actor is currently working on a number of projects, including Blood Heist and The Long Home.
When Jessica Alba played Kirsten, one of the popular girls of South Glen South High School, all eyes were on her. Nearly six years later, when Alba portrayed Sue Storm of the Fantastic Four, it's like she was invisible.
After Never Been Kissed, Alba took on a variety of roles in addition to the Fantastic Four lead. She played one of the many female protagonists in Garry Marshall's Valentine's Day, which featured a star-studded roster of talent including Bradley Cooper, Taylor Swift, Anne Hathaway and more.
Alba is currently filming the first season of L.A.'s Finest, where she plays drug enforcement agent Nancy McKenna, starring alongside Gabrielle Union.