1. Amanda Bynes as Viola Hastings:
Iconic quote: There are so many, but right now I can't get "I've got a lifetime of knowledge" out of my head.
Dreamworks / Courtesy Everett Collection Amanda Bynes now:
What she's up to now: After taking a break from the public eye, Amanda recently returned to social media with a few new TikToks and a podcast.
Amanda Bynes and Paul Sieminski: The Podcast / Via youtube.com 2. Channing Tatum as Duke Orsino:
Iconic quote: "It's just like what Coach says before every game: Be not afraid of greatness, some are born great, some achieve greatness, and some have greatness thrust upon them. I think our best chance to be great here today, is to have you play."
Dreamworks / Courtesy Everett Collection Channing Tatum now:
What he's up to now: Of course, after She's the Man (and Step Up ), Channing's acting career exploded with roles in the Magic Mike trilogy and 21 Jump Street . Most recently, he's starred in The Lost City and Magic Mike's Last Dance . He has also adorably written two children's books inspired by his daughter.
Nbc / Nathan Congleton / NBC via Getty Images 3. Laura Ramsey as Olivia Lennox:
Iconic quote: " I heard he dumped you. He dumped you big. It was just like a big, huge dumping."
Dreamworks Laura Ramsey now:
What she's up to now: After taking an eight-year break from acting, Laura returned in 2023 to star in the Lifetime film A Rose for Her Grave: The Randy Roth Story .
Paul Archuleta / Getty Images 4. Alexandra Breckenridge as Monique:
Iconic quote: "Girls with asses like mine do not talk to boys with faces like yours."
Dreamworks /Courtesy Everett Collection Alexandra Breckenridge now:
What she's up to now: Alex has starred as Mel on the hit Netflix series Virgin River since 2019. She was also on This Is Us and The Walking Dead .
Netflix 5. Jonathan Sadowski as Paul:
Iconic quote: "Just remember, inside every girl, there's a boy. That came out wrong but you know what I mean."
Dreamworks Jonathan Sadowski now:
What he's up to now: Jonathan is best known for starring as Josh on the underrated sitcom Young & Hungry . More recently, he's appeared on Sex/Life and The Good Doctor .
Amanda Edwards / Getty Images 6. David Cross as Principal Gold:
Iconic quote: "*sung* Welcome to, Illyria, welcome, welcome, welcome, welcome, welcome, welcome, welcome, welcome... to Illyria! I just wanted to say welcome."
Dreamworks David Cross now:
What he's up to now: David Cross had quite the comedy career even before She's the Man , including his iconic role as Tobias Fünke on Arrested Development . Most recently, he's appeared in shows like Station Eleven and What We Do In the Shadows , and the recent film You Hurt My Feelings .
Jose Perez / GC Images 7. James Snyder as Malcolm:
Iconic quote: "Ladies and gentlemen, I hate to say 'I told you so' but I just...[Principal Gold pushes him away]. "
Dreamworks James Snyder now:
What he's up to now: Since She's the Man , James largely pivoted to a theater career with roles in If/Then opposite Idina Menzel and playing Harry Potter in Harry Potter and the Cursed Child. He was ultimately fired from Cursed Child over misconduct allegations from his costar.
Gabe Ginsberg / Getty Images 8. Robert Hoffman as Justin:
Iconic quote: "I did not cry during that game. I had something in my eye."
Dreamworks Robert Hoffman now:
9. Brandon Jay McLaren as Toby:
Iconic quote: "How come when I wanted to ask Eunice out everyone made fun of me, but then Sebastian likes her and suddenly she's cool? Screw you guys. I hate high school."
Dreamworks Brandon Jay McLaren now:
What he's up to now: Most recently, Brandon has appeared on several TV shows like Snowfall , The Rookie, Everything's Trash , and a main role on Turner & Hooch .
Amy Sussman / The Hollywood Reporter via Getty Images 10. Clifton Murray as Andrew:
Iconic quote: "Some guys just walk in the light you know."
Dreamworks Clifton Murray now:
What he's up to now: Clifton pivoted from acting and is a member of the Candian music group, The Tenors.
Jeremychanphotography / Getty Images 11. Jessica Lucas as Yvonne:
Iconic quote: "That's just something I'll always have to live with."
Dreamworks Jessica Lucas now:
What she's up to now: Jessica has had a big TV career since She's the Man , most notably (and recently) starring on The Resident .
Fox / FOX Image Collection via Getty Images 12. Amanda Crew as Kia:
Iconic quote: "I miss you, Sebastian. I've been thinking about you a lot. Especially at night."
Dreamworks Amanda Crew now:
What she's up to now: Amanda starred in more movies like Charlie St. Cloud and Sex Drive and starred as Monica Hall on Silicon Valley until 2019.
Rodin Eckenroth / Getty Images 13. James Kirk as Sebastian Hastings:
Iconic quote: "I think I'm gonna like this school."
Dreamworks James Kirk more recently in 2017:
What he's up to now: Most recently, James has acted on the series Something Between and the Hallmark Christmas movie Welcome to Christmas and has done voice work for Hatchimals: Adventures in Hatchtopia and CoComelon Lane .
Eike Schroter / Disney General Entertainment Content via Getty Images 14. Emily Perkins as Eunice:
Iconic quote: "Soccer is the world's favorite sport."
Dreamworks Emily Perkins most recently in 2014:
What she's up to now: Emily has stepped away from acting since 2014, but she notably played the role of Becky Rosen on Supernatural .
The CW 15. Vinnie Jones as Dinklage:
Iconic quote: "Here at Illyria, we don't discriminate BASED ON GENDER."
Dreamworks Vinnie Jones now:
What he's up to now: Vinnie, who used to be a professional soccer player prior to starring in She's the Man , has most recently acted on Law and Order: Organized Crime (pictured above) and appeared on the Australian Masked Singer .
Nbc / NBCU Photo Bank via Getty Images 16. Julie Hagerty as Daphne:
Iconic quote: "Nonsense! You don't need a man to wear a beautiful dress!"
Dreamworks /Courtesy Everett Collection Julie Hagerty now:
What she's up to now: Julie is a prolific actor who has appeared in many projects like Airplane! and Airplane II long prior to She's the Man . Most recently, she has appeared on the show Black Monday and the films Somebody I Used to Know, A Christmas Story Christmas, and The Out-Laws.
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