What The Cast Of Never Been Kissed Looks Like Today

"Never Been Kissed" is one of those underappreciated rom-coms that has well and truly stood the test of time. The 1999 film follows Josie (Drew Barrymore), a young copywriter, assigned an undercover story — posing as a high school student to write an exposé about the high school scene. Josie successfully fools the students and teachers at a local school with the help of her brother, Rob (David Arquette), who joins his sister to try to get a second shot at playing baseball. Things soon get a little complicated when Josie develops feelings for her English teacher, Sam (Michael Vartan).

Although "Never Been Kissed" might have a few problematic aspects in a post #MeToo world — like, you know, that whole teacher-student flirtation — it remains a '90s classic. For one thing, it had an absolutely iconic cast — along with Barrymore, who was already a rom-com favorite at the time, the film featured comedic geniuses like Molly Shannon and John C. Reilly and also had a few cameos from stars-to-be like Octavia Spencer, Jessica Alba, and James Franco. We've done a little digging to find out what the cast of "Never Been Kissed" is up to today.

Drew Barrymore is a talk show host and all-around icon

Drew Barrymore was already a massive star by the time she appeared as Josie, the budding reporter, in 1999, having featured in "E.T. the Extra-Terrestrial," "Scream," "The Wedding Singer," and "Ever After." Following "Never Been Kissed," Barrymore continued her career as one of the biggest rom-com stars of her generation with roles in "Charlie's Angels," "50 First Dates," "Fever Pitch," and "Music and Lyrics."

Despite her huge success as a performer, Barrymore's career slowed down in the 2010s. She later told the Los Angeles Times that acting didn't feel "emotionally available to me right now." She added, "I just need to be myself. I struggle to be someone else ... I just can't see acting right now."

In 2019, she entered a new era as a talk show host with "The Drew Barrymore Show." It became a huge hit thanks to Barrymore's empathetic, honest approach to interviewing. Before this accomplishment, she divorced her husband, Will Kopelman, in 2016 — the pair now co-parent their two daughters, Olive and Frankie.

David Arquette married twice and continued acting

Before playing Josie's brother, Rob, in "Never Been Kissed," David Arquette had risen to prominence in the '90s and starred alongside Drew Barrymore in the "Scream" franchise as Dewey. Since playing Rob, Arquette's career has been primarily defined by his ongoing role in the "Scream" films. 

Arquette's first marriage was one of his biggest claims to fame. He married Courteney Cox in 1999 after they met on the set of "Scream" in 1996. However, by 2010, Cox and Arquette had separated. Arquette told People he struggled with Cox's fame as Monica in "Friends." "In the acting world, in general, you're always going on this roller coaster of popularity and not able to get a job," he said. "So it's like this weird thing. And then, when you're comparing yourself to someone who's at the top of the television iconic world, it's kind of hard to put yourself there."

Arquette married journalist Christina McLarty two years after his divorce from Cox was finalized. The pair now have two children, and Arquette also has a child from his marriage to Cox. As of 2023, Arquette had two upcoming acting projects: "The Unholy Trinity" and "Chuck Hank and the San Diego Twins."

Michael Vartan starred in Alias and a number of other TV shows

Every good rom-com needs a great romantic lead, and we certainly got that with Michael Vartan as the dashing English teacher Sam Coulson. Vartan started in film and TV in the '90s, appearing in "Friends" in 1997 as Richard's son, with whom Monica has a brief flirtation. "Never Been Kissed" was one of his first significant roles. A couple of years later, he landed a leading part in "Alias" as CIA agent Michael Vaughn. He went on to appear in 96 episodes of the show from 2001 through 2006. He then starred in "Hawthorn" until 2011. More TV roles followed this in shows like "Ring of Fire," "Bates Motel," and "The Arrangement."

As of 2023, Vartan hadn't appeared in any new projects since 2018. Although Vartan has portrayed several prominent TV characters over the years, his role in "Never Been Kissed" remains one of his favorite to date. "This movie's been a huge part of my life," he told his co-star Drew Barrymore during a special reunion episode on her talk show. "Every time I'm stopped it's always, 'Never Been Kissed,' so it's a pretty amazing thing to be a part of."

John C. Reilly is one of the most recognizable faces in both comedy and drama

John C. Reilly has become one of those actors who seems to be in just about everything. Not only has he shown himself to be a gifted comedian in films alongside Will Ferrell like "Anchorman," "Step Brothers," and "Holmes and Watson," but he's also appeared in a number of acclaimed dramas such as "Magnolia," "Gangs of New York," "The Aviator," and "Licorice Pizza." He has been in so many great films, FiveThirtyEight even joked that there should be a John C. Reilly Award for the actor who appears in the most Academy Award-nominated films in one year — because, you know, he always turns up in so many!

As Reilly told The Talks in 2019, he never intended to act in so many comedies: "I never set out to be a comedian, I never thought I would even be a funny actor, I was just trying to be an actor. I grew up doing theater and musicals," he said. But of course, he had a natural talent for it — and "Never Been Kissed" was only the beginning!

Molly Shannon has appeared in dozens of comedic roles

Molly Shannon is another household name known for her comedic skill and dozens of iconic turns over the years. In "Never Been Kissed," Shannon played Anita, Josie's friend at the office who is also on the hunt for love — though she certainly takes a different approach than Josie. Shannon was already known for her comedy chops, having appeared on "Saturday Night Live" since 1995. She continued acting on "SNL" until 2010. She also had roles in shows like "Sex and the City," "30 Rock," "Pushing Daisies," "Raising Hope," and "Will & Grace" to name just a few, and appeared in dozens of films, including "Marie Antoinette," "Evan Almighty," and "Promising Young Woman."

Even though Shannon's career has seen her take on dozens of recognizable characters, she still doesn't view herself as a star. "I appreciate everything because I worked so hard to get it, but no, I've never thought about [being an icon] too much," she told Glamour. Over the years, her commitments have shifted. "It's really all about my children, my family, because I love being a mother. Show business is very, very secondary to them for me," she said. Shannon lives with her husband, Fritz Chestnut, and has two children, Stella and Nolan.

Leelee Sobieski retired in 2012 and has been focusing on being a mom

Leelee Sobieski portrayed Josie's friend, Aldys, a misfit who takes Josie under her wing at school. Sobieski already had a burgeoning career before "Never Been Kissed," having acted in several TV shows and the film "Deep Impact." She went on to star in the titular role in a mini-series about Joan of Arc. She also appeared in "Eyes Wide Shut, " "Joy Ride," "The Wicker Man," "Public Enemies," "Drop Dead Diva," and many other projects. She was even nominated for two Golden Globes for her work.

However, by 2012, Sobieski seemed to be tiring of acting. "Ninety percent of acting roles involve so much sexual stuff with other people, and I don't want to do that," she said to Vogue. " Then, in 2016, she explained to Us Weekly, "I don't do movie stuff anymore. I am totally an outsider! I ... am just a mom and an outsider ... I am just focused on my kids. I think that's mainly why I stopped." She added that she might consider doing another role when she was much older and could play a "sweet grandma." We'd totally watch that!

Cress Williams starred in Living Single and went on to star in a number of TV shows

Cress Williams brought George to life in "Never Been Kissed," one of the team members helping Josie act like a teen from behind the scenes. Williams went on to have a bustling career in TV — his resume includes credits in "The District," "House M.D.," "Veronica Mars," "The West Wing," "ER," "Grey's Anatomy," "Hart of Dixie," and "The Flash." "I was a poor kid. I grew up watching film and television but primarily television," Williams told Variety. He studied acting at college, moved to Hollywood, and began his career.

As Williams went on to explain, he's happy with his life now — but he didn't always feel that way. "I got to where I wanted to go, but through a little bit of a detour," he said. "When I first started working in film and television I hated myself — I didn't like what I was doing at all." Williams has been married twice — first to Simbi Khali from 2000 through 2011 and then to fellow actor from "Hart of Dixie," Kristen Torrianni, in 2013.

Octavia Spencer starred in The Help, Ma and Hidden Figures – and racked up three Oscar nominations

These days, we all know Octavia Spencer as a multi-Oscar nominated (and one-time winning) actor — but back in 1999, when she had a cameo in "Never Been Kissed" as Josie's colleague, she was practically unknown. Throughout the early 2000s, she built up a strong CV, appearing in numerous hit shows like "ER," "Chicago Hope," "Malcolm in the Middle," and "NYPD Blue." After years of TV and film cameos, she finally landed a break-out role in the drama about American segregation and racism, "The Help," playing Minny, a 1960s maid alongside Emma Stone, Jessica Chastain, and Viola Davis. Roles followed this in "Mom," "Hidden Figures," "The Shape of Water," and "Ma."

Since 2008, Spencer has also worked as a producer. In recent years, she's produced "Green Book" and "Ma," amongst other projects. "The most important role for me is producer because I can generate my own work," she told The Hollywood Reporter. "Anything that I'm not being offered, I can find someone to write."

Jessica Alba also found fame after Never Been Kissed

Jessica Alba has become a household name since starring in "Dark Angel," "Fantastic Four," and "Sin City" in the early 2000s — of course, all of this came after she played Kirsten, one of the popular girls in "Never Been Kissed," her first film role. Alba's career has taken her far since her time in the romantic comedy. As she told Drew Barrymore on her talk show, she actually celebrated her "17th birthday on the set". Luckily, the film could not have been more enjoyable to create. "It felt like camp, but you also, I mean you really took so many people under your wing and guided them and a lot of us were really just starting out."

Alba married Cash Warren in 2008, and they soon had three children: Honor, Haven, and Hayes. In a 2023 Instagram post, Alba described them as "the greatest gift in this life." She now runs The Honest Company, a wellness brand centered on bringing consumers products they can trust.

Sean Whalen is still working as both an actor and a writer

Sean Whalen appeared in "Never Been Kissed" as Merkin, one of Josie's more annoying co-workers. He was already a familiar face, having secured parts in "Men in Black," "Twister," "Waterworld," and "Friends." After the film, he collaborated with Drew Barrymore again in "Charlie's Angels," and also landed roles in "NYPD Blue," "Scrubs," "Hannah Montana," "Lost," and "The Bold and the Beautiful." By the looks of things, he's still swamped. In 2023, he took on a total of six roles in a mixture of TV shows, films, and video games.

As Whalen told Cryptic Rock in 2016, he still likes acting in comedies more than anything. "My first love is comedy, hands down," he said. "I started at The Groundlings, I am teaching comedy at Studio 4: James Franco's Film & Acting School in North Hollywood, and I am running the Comedy department, building it from the ground floor. I love Comedy improv, doing Comedy, making the crew laugh, that has always been my favorite."

James Franco became a superstar after his film debut

You may have spotted James Franco as one of the popular boys in "Never Been Kissed." It was one of his first roles — however, he soon shot to fame as Daniel in "Freaks and Geeks." Over the next few decades, he became one of Hollywood's biggest stars, racking up credits in the 2002 "Spider-Man," "The Wicker Man," "Milk," "127 Hours," "Howl," "This is the End," "The Disaster Artist," and more. He also began working as a producer as early as 2005.

Although Franco has had a wildly successful career, his personal life hasn't always been simple. In fact, over the years, he has struggled with alcohol and sex addiction. In 2019, two women accused him of exploiting them while he was their acting teacher. As Franco said on "The Jess Cagle Podcast," he had "been doing a lot of work" on himself. He added, "I didn't want to hurt people" (via The Guardian). As of 2023, Franco was in a relationship with Isabel Pakzad.

Martha Hackett starred in Star Trek

Martha Hackett had a small cameo role in "Never Been Kissed" as Mrs. Knox, the quirky, chipper teacher who forces Josie to wear a sombrero on her first day — yikes! Hackett had already been acting for several years, having worked in theater as a young woman and then appearing in a number of TV shows throughout the '80s and '90s. Some of her most prominent roles following "Never Been Kissed" include "NCIS," "Perception," "The Mindy Project," and "Days of Our Lives."

Hackett's biggest claim to fame was playing Seska in "Star Trek: Voyager" from 1995 to 2001. As of 2023, her last part was in the TV movie "A Mother Knows Worst" in 2020. She also still appears at fan conventions to discuss her career and role in "Star Trek." However, for the most part, it seems she's leading a quieter life these days.

Jenny Bicks has always been more of a writer than an actor

You might not remember Jenny Bicks in "Never Been Kissed" — she had a tiny role as Miss Haskell. However, you may not have realized that she also wrote the screenplay for the film. A well-known rom-com writer of the era, she was responsible for episodes of "Almost Perfect," "Dawson's Creek," "Sex and the City," and "The Big C," along with the film "What a Girl Wants." Additionally, she produced several TV shows. As of 2023, her latest project was "Welcome to Flatch," a Fox/Hulu mockumentary about small-town cousins.

Although Bicks may appear to have a flashy career as a film and TV writer and producer, her life seems happy and simple. According to her X, formerly known as Twitter, profile, she is a "lover of monkeys" and a "hater of olives." "Welcome to Flatch" was canceled in 2023 — "It is with a broken heart and a Barbarita that I announce the untimely demise of 'Welcome To Flatch,'" she wrote at the time. "I am fiercely proud of the show and all the insanely talented folks who made it happen. Thank you @paulfeig, my partner in crime." We don't know what Bicks will bring us next, but we have no doubt it will be another classic in the making.