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    "She's All That" Came Out 21 Years Ago, So Here Are Side-By-Sides Of The Cast Then Vs. Now

    "Kiss meeee, beneath the milky twilight…"

    I can hardly believe that it's been over 21 years since She's All That came out back in 1999 — this movie can legally drink!


    "Am I a bet? Am I a FUCKING bet?!"

    And when I did a rewatch the other day, I couldn't help but notice just how stacked this cast really is! (Seriously, A++++ casting.) Here's what everyone's up to now:

    1. Freddie Prinze Jr. as Zack Siler

    Miramax Films, Instagram/Freddie Prinze Jr. / Via

    Movie role: Freddie played Zack, the popular high school student who made a bet that he could turn any girl into prom queen in six weeks.

    Post-She's All That: Shortly after the movie, Freddie starred in the Scooby Doo franchise, Freddie, Summer Catch, Head Over Heels, 24, and that one Friends episode. More recently he starred as a voice on Star Wars Rebels and made a brief voice cameo in The Rise of Skywalker. He will appear in the upcoming Punky Brewster spinoff. And, yes, he's still married to Sarah Michelle Gellar!

    2. Rachael Leigh Cook as Laney Boggs

    Miramax Films, Matt Winkelmeyer / Getty Images

    Movie role: Rachael played Laney, a teen who was perfectly gorgeous and awesome even when she wore glasses and a falafel hat, thank you very much.

    Post-She's All That: Rachael starred in Josie and the Pussycats and had arcs on Dawson's Creek, Las Vegas, and Psych. More recently, she starred on Perception, and has done voice work on Robot Chicken since 2006. You can also catch her in Hallmark movies like A Blue Ridge Mountain Christmas and Frozen in Love.

    3. Jodi Lyn O'Keefe as Taylor Vaughan

    Ari Perilstein / Getty Images, Miramax

    Movie role: Jodi Lyn played Taylor Vaughan, Zack's ex and the prom queen candidate to beat.

    Post-She's All That: You probably remember her recurring roles on Prison Break and Two and a Half Men. Most recently she had a major role as Jo on The Vampire Diaries and even appeared on its spinoff, Legacies.

    4. Matthew Lillard as Brock Hudson

    Frazer Harrison / Getty Images

    Movie role: Matthew played Taylor's new boyfriend, Real World contestant Brock Hudson.

    Post-She's All That: It's hard to think of Matthew Lillard without thinking of Scooby Doo! He starred in the live-action movies alongside Freddie, and has voiced Shaggy in countless other videos and games. More recently, he's appeared on Bosch, Twin Peaks and Good Girls.

    5. Anna Paquin as Mackenzie Siler

    Miramax, Frazer Harrison / Getty Images

    Movie role: Anna played Zack's younger sister, Mackenzie — the one responsible for THAT big movie makeover moment.

    Post-She's All That: Shortly after the movie, Anna landed the role of Rogue in the X-Men movies. Oh, and you may remember her from a little show called True Blood. Most recently, Anna has appeared on Flack and The Affair.

    6. Kieran Culkin as Simon Boggs

    Miramax, Jamie Mccarthy / Getty Images

    Movie role: Kieran played Laney's younger brother, Simon, who Zack protects from bullies in the cafeteria in a very gross pube-related scene.

    Post-She's All That: Kieran acted in movies like The Cider House Rules and Scott Pilgrim vs. the World, but now he's known for playing the role of Roman Roy on Succession.

    7. Dulé Hill as Preston

    Miramax, David Livingston / Getty Images

    Movie role: Dulé played Preston, one of Zack's ~popular~ friends.

    Post-She's All That: Directly after She's All That, Dulé starred as Charlie Young on The West Wing until 2006. Then, directly after that he starred on Psych. More recently, he's starred on Ballers and Suits and recently filmed a Psych TV movie, due out this year.

    8. Kevin Pollak as Wayne Boggs

    Jean-baptiste Lacroix / Getty Images, Miramax

    Movie role: Kevin played Laney's father, Wayne, who rigged their pool area with some very festive lights.

    Post-She's All That: Kevin has appeared on countless shows and movies, before and after She's All That: A Few Good Men, The Usual Suspects, Casino, The Wedding Planner, and The Santa Clause: 2 & 3, to name a few. But, most recently, he's starred on The Marvelous Mrs. Maisel as Joel's father, Moishe Maisel.

    9. Elden Henson as Jesse Jackson

    Miramax, Gabe Ginsberg / Getty Images

    Movie role: Elden played Laney's BFF Jesse.

    Post-She's All That: Elden appeared in both The Hunger Games: Mockingjay movies as Pollux and starred in Daredevil as Foggy Nelson.

    10. Lil' Kim as Alex

    Gregg Deguire / Getty Images, Miramax

    Movie role: Lil' Kim played Alex, one of Taylor's friends.

    Post-She's All That: Lil' Kim released four studio albums since her brief foray into acting for She's All That, including 9 which just came out in October. She won a Grammy in 2002 for her collab on "Lady Marmalade" with Christina Aguilera, Mya, and Pink.

    11. Gabrielle Union as Katie

    Miramax, Frazer Harrison / Getty Images

    Movie role: Gabrielle played Katie, another member of Taylor's friend group.

    Post-She's All That: After getting her start in TV, this was actually Gabrielle's big movie debut. Right after She's All That, Gabrielle appeared in 10 Things I Hate About You, Love & Basketball, and Bring It On. More recently she has starred in movies like Think Like A Man, Think Like A Man Too, and The Birth of a Nation, and she has starred on TV in Being Mary Jane and L.A.'s Finest.

    12. Tamara Mello as Chandler

    Miramax, Tamara Mello/Instagram / Via Instagram: @

    Movie role: Tamara played Chandler, another member of the popular crew.

    Post-She's All That: After She's All That, Tamara starred on Popular. More recently, she's appeared on School of Rock and Children's Hospital.

    13. Clea Duvall as Misty

    Miramax Pictures, Valerie Macon / Getty Images

    Movie role: Clea played Misty, Laney's not very nice fellow art class student.

    Post-She's All That: The same year as She's All That, Clea starred in But, I'm a Cheerleader and Girl, Interrupted to name just a couple of her movies. On TV, she's appeared in Heroes, American Horror Story, The Lizzie Borden Chronicles, Broad City, Veep, and The Handmaid's Tale.

    14. Usher Raymond as Campus DJ

    Miramax, Paras Griffin / Getty Images

    Movie role: Literally Campus DJ! A thing that apparently exists at high schools?!

    Post-She's All That: Usher has released seven albums since then and won eight Grammys! Acting-wise, he recently made a cameo in 2019's Hustlers.

    15. Milo Ventimiglia as Soccer Player

    Miramax, Matt Winkelmeyer / Getty Images

    Movie role: An unnamed soccer player that Zack convinces to help clean Laney's house.

    Post-She's All That: Gilmore Girls, Heroes, This Is Us — need I say MORE?

    16. Sarah Michelle Gellar as Girl in Cafeteria

    Jean-baptiste Lacroix / Getty Images, Miramax

    Movie role: An uncredited cameo as a girl in the cafeteria.

    Post-She's All That: She's Buffy the friggin' Vampire Slayer! Plus, Cruel Intentions, the Scooby Doo franchise, and Ringer. And, as mentioned above, she's still married to Freddie! *heart eyes emoji*

    Sadly, Paul Walker died in 2013 and Alexis Arquette died in 2016 — they played Dean Sampson (Zack's mean friend who made the bet with him) and Mitch (from Laney's performance art night) respectively.