Never Been Kissed is one of those timeless rom-coms. Drew Barrymore stole our hearts as Josie Geller, the Chicago Sun-Times reporter who gets her big break going undercover as a senior at a local high school. Along the way, Josie gains the confidence she lacked when she was growing up. The movie has the most epic ending when Josie gets her first kiss from Sam.
The romantic-comedy is one of those movies you can always rewatch. Drew is just so delightful, and Never Been Kissed totally captured the last year of the 1990s. The movie was released on April 9, 1999, and earned over $84 million at the box office. In honor of the 22nd anniversary, see the cast then and now.
Drew Barrymore
Drew Barrymore, 46, starred as Josie Geller, who goes back to high school for an undercover assignment. The year prior to Never Been Kissed, Drew starred in hits like Ever After and The Wedding Singer. The former child actress went on to star as Dylan in the 2000 film Charlie’s Angels and its 2003 sequel. She also starred in additional rom-coms like 50 First Dates, Fever Pitch, He’s Just Not That Into You, and more. She made her directorial debut with the 2009 film Whip It. Drew is currently hosting her own talk show, The Drew Barrymore Show. She has also released her own line of Flower cosmetics.
Drew married Tom Green in 2001, but they divorced a year later. She dated Fabrizio Moretti and Justin Long before marrying Arie Kopelman in 2012. They have two kids together. Their divorce was finalized in 2016.
Michael Vartan
Michael Vartan, 52, played Sam Coulson in Never Been Kissed. A couple of years after the hit rom-com, Michael began starring in the ABC series Alias, which ran from 2001 to 2006. He went on to star in TV series like Hawthorne and The Arrangement. He also appeared in movies like Monster-In-Law, One Hour Photo, Colombiana, and more. His most recent roles were in a 2018 episode of God Friended Me and the 2017 film Small Town Crime. Michael was married to Lauren Skaar from 2011 to 2014.
David Arquette
David Arquette, 49, starred as Rob Geller, Josie’s younger brother. The following year after Never Been Kissed, David reprised his role as Dewey in Scream 3. He returned for Scream 4 in 2011 and will be back for the franchise’s fifth film, which will be released in 2022. He’s had a number of movie and TV roles over the years. She starred in the ABC series In Case of Emergency and voiced Skully on Jake and the Never Land Pirates.
The actor also become a professional wrestler. He won the WCW World Heavyweight Championship in 2000. David recently released the documentary You Cannot Kill David Arquette about his attempt to return to wrestling. He was also featured in Soleil Moon Frye’s documentary Kid 90.
David married Courteney Cox in 1999. Their daughter, Coco, was born in 2004. They split in 2010, and their divorce was finalized in 2013. However, they remain close. He began dating Christina McLarty in 2011. The couple married in 2015. They have two sons together.
Jessica Alba
Jessica Alba’s role as Kirsten Liosis in Never Been Kissed was one of her first film roles. The 39-year-old had her breakout role in 2000 when she starred in the TV series Dark Angel. She received a Golden Globe nomination for her performance. Another one of her first leading roles was in the 2003 film Honey. She has since starred in Fantastic Four, Good Luck Chuck, Valentine’s Day, Sin City, Spy Kids: All The Time In The World, and more. Jessica starred alongside Gabrielle Union in the series L.A.’s Finest, which ran for two seasons.
Jessica co-founded The Honest Company in 2011. The consumer goods company sells baby, personal, and household products. The actress and businesswoman married Cash Warren in 2008. They have three children: Honor, Haven, and Hayes.
Marley Shelton
Marley Shelton, 46, played another Kirstin in Never Been Kissed. She went on to star in the 2001 film Sugar & Spice, which has become a cult favorite over the years. She reunited with David Arquette for Scream 4 in 2011 and will return for the fifth Scream movie in 2022. Marley’s had more roles over the years in Bubble Boy, Rampage, Grindhouse, and Sin City with Jessica Alba in 2005. She’s also starred in TV shows like Rise, The Lottery, and more. Marley married Beau Flynn in 2001. They have two daughters together.
James Franco
James Franco, 42, played Jason Wray, one of the popular kids, in Never Been Kissed. The 1999 flick was his first feature film. He went on to star as Harry Osborn in the initial Spider-Man trilogy, Pineapple Express, Milk, Date Night, Rise of the Planet of the Apes, Spring Breakers, This Is The End, and more. He earned an Oscar nomination in 2011 for Best Performance by an Actor in a Leading Role for his role in 127 Hours. He won the 2018 Golden Globe for Best Performance by an Actor in a Motion Picture – Musical or Comedy for his role in The Disaster Artist.
He also played Franco in several episodes of General Hospital. The actor starred in the Hulu limited series 11.22.63 and the HBO series The Deuce. His upcoming movies including Kill the Czar and The Long Home, which he’s also directing.
Leelee Sobieski
Leelee Sobieski, 37, played Aldys Martin, the girl who befriends Josie when she returns to high school. The same year as Never Been Kissed, Leelee starred in the TV miniseries Joan of Arc, which earned her Emmy and Golden Globe nominations. She was nominated for another Golden Globe for her performance in the 2001 miniseries Uprising. Her other notable films post-Never Been Kissed include Joy Ride, Here on Earth, and The Glass House. Her last roles were in the 2012 series NYC 22 and film Branded. She has since retired from acting and is now an artist. Leelee got engaged to Adam Kimmel in 2009. They have two kids together.
Molly Shannon
Molly Shannon, 56, played Josie’s co-worker Anita. At the time that Never Been Kissed came out, Molly was currently a cast member on Saturday Night Live. She was a full-time cast member from 1995 to 2001. She went on to have roles in How the Grinch Stole Christmas, Talladega Nights: The Ballad of Ricky Bobby, Me and Earl and the Dying Girl, Other People, Private Life, and recently Promising Young Woman. She has also voiced the role of Wanda in the Hotel Transylvania movies.
In terms of TV, Molly starred in the HBO series Divorce from 2016 to 2019. She’s also appeared on The Other Two, Kath & Kim, Glee, and more. She appeared in Katy Perry’s 2017 music video for “Swish Swish.” Molly married Fritz Chesnut in 2004. They have two kids.
John C. Reilly
John C. Reilly, 55, played Josie’s boss, Augustus Strauss. In the years after Never Been Kissed, John was nominated for an Oscar for his performance in the 2002 musical Chicago. He starred in movies like Gangs of New York, Talladega Nights: The Ballad of Ricky Bobby, Step Brothers, Kong: Skull Island, and voiced the title character in the Wreck It Ralph movies. He earned a Golden Globe nomination for his performance in the 2018 film Stan and Ollie. He created and starred in the Showtime series Moonbase 8 in 2020.
Octavia Spencer
Octavia Spencer, 50, played Cynthia, another one of Josie’s co-workers. Octavia had a number of roles after Never Been Kissed, but her breakout role was playing Minny in the 2011 movie The Help. She won the Oscar for Best Supporting Actress. She also earned critical acclaim for her performance in the 2013 film Fruitvale Station. The actress received two more Oscar nominations for Hidden Figures and The Shape of Water. Her other notable movies include Snowpiercer, Get On Up, Gifted, Luce, The Shack, and Ma.
She recently starred in the Apple TV+ drama series Truth Be Told and the Netflix limited series Self Made, which earned her an Emmy nomination. Octavia’s next role is in the 2021 Netflix film Thunder Force.
Jeremy Jordan
Jeremy Jordan, 47, played Guy Perkins in Never Been Kissed. According to his IMDb profile, his last film role was in the 2011 film The Absent. He is also a singer.