Here's What The Cast Of She's All That Looks Like Now

In the '80s, '90s, and '00s, the rom-com reigned supreme. Flicks like "When Harry Met Sally...", "Notting Hill," "How to Lose a Guy in 10 Days," and more are still go-tos for audiences looking to swoon, and the actors who starred in them — Meg Ryan, Julia Roberts, and Kate Hudson, just to name a few — are still key players in Hollywood. Needless to say, during those three decades, rom-com fans had it made in the shade.

One of the most memorable rom-coms from the latter half of that era would have to be "She's All That." The movie was a modern reimagination of "Pygmalion," featuring a popular high school boy who turned a nerdy high school girl into a prom queen in a matter of weeks. It was an absolute hit — the movie cost $10 million to make and ended up raking in over $100 million worldwide — and its stacked cast is certainly a big reason why. And yes, many of the movie's stars are still working actors today. Here's what the cast of "She's All That" looks like now.

The star of "She's All That" has been in Hollywood since she was a teenager. She got her start acting on the silver screen, but Rachael Leigh Cook is also a Hallmark star and has been producing films regularly for over a decade. Still, to this day, Cook is best known for her role as Laney Boggs in "She's All That," and it's a role that she is grateful for. "I definitely thought that the movie had a ton of charm as a whole. It sounds corny to say, but I just felt happy to be in it," Cook said of the film in an interview with People.

In the late 2010s, it was announced that Hollywood was producing a gender-swapped remake of the late '90s hit, called "He's All That."  In December 2020, there was another big announcement regarding the remake: Cook would be in the movie — but she would not reprise the role of Laney. The film, which premiered on Netflix in 2021, starred Addison Rae and Tanner Buchanan; Cook played Anna Sawyer, the mother of Rae's character. "I'm thrilled to be reunited with so many familiar faces! This version has a great new spin that I think people will really enjoy," Cook said of joining the cast, per Variety.

Freddie Prinze Jr. is still one of the most iconic heartthrobs from the late '90s and early '00s. In "She's All That," Prinze Jr. played Zack Siler, a popular jock who enters an initially ill-intentioned bet with his friend Dean Sampson, who was played by the late Paul Walker. Prinze Jr. also landed the part of Fred in the live-action "Scooby-Doo" movies, as well as Ray Bronson in the famed "I Know What You Did Last Summer" franchise. Fans were thrilled to learn that the horror series was being rebooted with a new generation of talent, but they were equally excited that stars from the original film — including Jennifer Love Hewitt and Prinze Jr.'s costar-turned-wife, Sarah Michelle Gellar — would be reprising their roles. Prinze Jr. got in on the reprisal, too, taking on the role of Ray once again.

Actors aren't always interested in joining reboots, but Prinze Jr. was eager to revisit the character of Ray all of these years later. "Time hasn't been good to Ray. That was attractive to me — I've never gotten the opportunity to play that before. Ray is a guy who never spent a dollar he didn't work really hard to make. He's in denial. He's not the tough guy he used to be. Julie has used her trauma to help build her career and move her life forward," Prinze Jr. said in an interview with Variety.

Dulé Hill has acted in some major projects throughout his career. Early on, he played Preston in "She's All That" and had a role in "Holes." He was also part of the cast of "The West Wing" and starred in "Psych," the last of which followed up with a few made-for-TV movies after the series wrapped. Hill has worked on a few other notable series, including "Suits" and "Bel-Air," the dramatic reboot of "The Fresh Prince of Bel-Air." The actor also starred in another reimagination of an old favorite, "The Wonder Years."

The 2020 version of "The Wonder Years" followed a Black family living in Montgomery, Alabama, in the 1960s. The show only lasted for two seasons, but it garnered great reviews and boasted an excellent cast, with Don Cheadle narrating the show and Hill playing Bill Williams, the father. "America is full of millions of unique and diverse stories, and this is just one of them. The original 'Wonder Years' was one story, this is another, and there's many more to share after this one. But it's my honor and my joy to share this story with the viewing audience at this time," Hill told Entertainment Weekly of the series.

To some, Matthew Lillard is a comedic icon, hailed for his work as Brock Hudson in "She's All That" (as well as his appearance in the gender-swapped sequel). To others, he's better known for his work in horror, notably taking on different roles in multiple "Scream" installments over the years. He's also played Shaggy in live-action and animated  "Scooby-Doo" projects, making him almost inextricably linked to the iconic character.

In 2023, Lillard took on another high-profile role: William Afton in "Five Nights at Freddy's." Lillard joined Josh Hutcherson for the film adaptation of the wildly popular video game, ushering in a new era of horror movie IP. The film was a major financial success, and though Lillard had been part of successful franchises before, it's something he certainly does not take for granted. "It's exciting to be a part of this thing that has become an international sensation. I realize that these opportunities don't come around that often. It's been a really rich, joyful moment because I can sort of sit back and appreciate it on a deeper level," he said in an interview with The Hollywood Reporter. He also wanted audiences to recognize that he's a longtime industry professional. "I sort of want to quote LL [Cool J], 'Don't call it a comeback, I've been here for years,'" Lillard said.

Anna Paquin was a huge get for the cast of "She's All That." She played Mackenzie Siler in the film, and the role came about five years after she won an Oscar for her very first movie, "The Piano." After the classic '90s rom-com came out, Paquin remained a steady working actor in Hollywood, finding work in projects like "Almost Famous," "True Blood," and "The Irishman." Paquin has also been part of multiple independent films, like 2022's "A Bit of Light." "My first love was independent filmmaking. That's how I entered the film industry. I was working with people who were all about telling stories and telling them with integrity and truth," Paquin said in an interview with People.

In recent years, Paquin has been dealing with undisclosed health struggles that have impacted her mobility.  "It hasn't been easy," she said in the aforementioned interview of her health journey. However, Paquin intends to continue working. "The idea that her career is over or that she's winding down the amount of acting she's doing is absurd ... She is confident enough with the progress of her treatment to continue to work at the highest level possible," a source told InTouch in 2025.

When looking at a list of the most beloved movies from the late '90s and early '00s, there's a good chance Gabrielle Union was part of the cast. Union was in "Bring It On," "Deliver Us from Eva," "10 Things I Hate About You," "Love & Basketball," and, of course, she played Katie in "She's All That." Union's career hasn't slowed since then, with "Daddy's Little Girls," "Think Like a Man," and "Being Mary Jane" among her credits. On top of it all, Union almost starred in the iconic TV drama "Scandal."

In 2026, Union teamed up with NBA star Stephen Curry to bring the movie "GOAT" to life, an animated movie about a goat with dreams of becoming a professional athlete. Union is married to former NBA star Dwyane Wade, who also has a part in the film, making it a family affair. "Learning how to be a better teammate, that is very relatable to me. I've seen basketball at its finest around the world at every talent level, and that's what this world is," Union said in an interview with Ebony. "I think it's always great when we can include each other in what we're doing. And this seems like a perfect fit, obviously," she said of being in a film with her husband.

Jodi Lyn O'Keefe played Taylor Vaughan in "She's All That," one of her very first acting roles. For the decades following her work in the classic rom-com, O'Keefe stayed busy as an actor, popping up in various episodes of hit TV series like "Charmed," "Boston Legal," "Criminal Minds," "Lost," and more. O'Keefe also had recurring roles on "Prison Break" and "The Vampire Diaries." In 2014, O'Keefe joined the cast of "Hit the Floor," a series about a dance team for a professional basketball team. The show had already aired for a season when O'Keefe got the job, but it was still a great experience. "I feel really lucky, it's been a really great experience for me. I was nervous at first because the cast has already been together for a year and they have such great camaraderie, so it's hard to be the new guy. However, they welcomed me with open arms and made me feel comfortable immediately. Gosh, I just had such a blast with them," she said in an interview with Vibe.

"Hit the Floor" ended in 2018, and since then, O'Keefe has only had two other screen credits, with her last one in 2021. The actor is active on social media, though, where she promotes a perfume brand she's modeled for and shares some of the movies and TV shows she's enjoyed.

Kieran Culkin has been acting since he was a kid. The world was first introduced to him when he played Fuller in the "Home Alone" franchise (of which his older brother was the star), and aside from a hiatus in the mid-2000s, Culkin has kept acting since childhood. Culkin played Simon Boggs in "She's All That," and "Scott Pilgrim vs. the World" and "Fargo" have been among his biggest credits since then. More notably, Culkin was Roman Roy in "Succession," a role for which he won an Emmy and Golden Globe, among other awards.

Culkin's awards didn't stop there. He won quite a few more awards, including a Golden Globe and an Oscar, for his work in "A Real Pain," which was written and directed by Jesse Eisenberg. Amazingly, Culkin almost passed on the role, even after agreeing to be part of it. "Things were coming. I freaked out, ran away," Culkin told Vulture of his career at the time. However, the script appealed to the actor. "It was one of the very, very, very rare scripts that I laughed out loud reading," he said. And ultimately, Emma Stone, one of the film's producers and his ex, talked him into staying. "She did an almost reverse-psychology thing on me," Culkin said of the conversation he had with Stone.

Music superstar Usher also popped up  "She's All That." The multi-talented entertainer played the school's D.J. in the film, and since that role, he's only had a handful of other acting gigs. He has, however, been wildly successful as a musician. He's won eight Grammys; charted 18 top 10 hits, nine of which went number one; and released nine top 10 albums, four of which went number one. He also hosted multiple Las Vegas residencies, and he celebrated 30 years as a recording artist in 2024 with a North American tour.

And how else did Usher kick off his celebratory 2024? He headlined the Super Bowl Halftime Show, of course. The singer had performed at the Halftime Show prior to 2024, but in 2024 the spotlight was on him. His performance featured his biggest hits from his decades in music, and it included appearances from Alicia Keys, Lil Jon, Ludacris, will.i.am, H.E.R., and Jermaine Dupri. Making those 24 hours even more impressive, Usher pulled off getting married and performing at the Super Bowl on the same day. "It was really a joyous moment between me and my wife and my children and my intimate and immediate family who was there. It was an abrupt thing. We decided at the last minute to do it," Usher said of his wedding in an interview with the New York Post.

Elden Henson played Jesse Jackson in "She's All That." Among his most notable projects after the rom-com were "Cast Away," "The Butterfly Effect," and both parts of "The Hunger Games: Mockingjay." Perhaps Henson's most memorable role, though, came before "She's All That." Henson played Fulton Reed in "The Mighty Ducks" movies, and he reprised his role for the series reboot that came out in 2021. "It was amazing. Steve's a great guy, and I feel very indebted to him. He created this franchise, and this franchise changed my life," Henson told Screen Rant of franchise creator Steven Brill.

Work comes to people in all sorts of unique ways, and such was the case for Henson's role in "The Mighty Ducks: Game Changers." "I actually ran into Steve at a Dodgers game, and he was talking about how he was pitching this idea. He's like, 'You would come back for an episode, right?' I was like, 'Of course. Anytime, man,'" Henson said. The actor appeared in two episodes of the show.

Powerhouse rapper Lil' Kim made her major acting debut in "She's All That." Since the film wrapped, Lil' Kim has been in a handful of movies and TV series, but most of her work has been as a musician. She released four of her five studio albums after the making of "She's All That," and she's been featured on several other musicians' tracks. In 2002, she won a Grammy for Best Pop Collaboration With Vocals for "Lady Marmalade," the chart-topping cover of the Labelle classic she made with Christina Aguilera, Pink, and Mya.

In 2026, in honor of the 25th anniversary of their Grammy-winning song, Lil' Kim and Mya reunited to perform it while on stage in Inglewood, California. This came a few months after Lil' Kim joined Keyisha Cole for her "The Way It Is" tour. The rapper also joined fellow R&B and hip-hop legends Ashanti, Busta Rhymes, Ja Rule, and more in 2026 for a special Valentine's Day performance.

The main "She's All That" characters were mostly played by actors who were relatively new to the industry. The role of Wayne Boggs, however, was played by Kevin Pollak, an actor who made his film debut in the '80s. And he kept working steadily as an actor following "She's All That," adding titles like "The Wedding Planner," "Entourage," "Drunk History," and "American Crime Story" to his resume. Pollak also appeared in all five seasons of "The Marvelous Mrs. Maisel," and in 2025, he joined the cast of "Tulsa King."

Pollak has shared the screen with many icons of the screen throughout his career, but for "Tulsa King," he got to team up with Sylvester Stallone. On an episode of "The Rich Eisen Show," Pollak was nothing short of effusive when talking about the "Rocky" star." "He's an inspiration and has been for decades upon decades," Pollak said.