She's All That Turns 22! See the Cast of the Teen Classic Then and Now

Rachael Leigh Cook (Laney Boggs) 

She’s All That was unquestionably the kick-off to Cook’s career. Since her days as dorky Laney, she’s gone on to appear in many different shows, several of which involved voice roles such as Robot Chicken. She also recently appeared in several Hallmark Channel films, and in 2017, she made a cameo in Khalid’s “Young, Dumb and Broke” music video. In 2020, she announced she was joining the gender-swapping remake of the film, the upcoming He’s All That.

She has two kids with ex-husband and actor Daniel Gillies, whom she married in 2014; they divorced in 2020.

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Freddie Prinze Jr. (Zack Siler)

Other than his role as hot-shot Zack in the film, Prinze may be best known for portraying Fred in the Scooby-Doo film series. He starred in a short-lived 2005 sitcom about his own life, had a recurring role in 24 in 2010 and recently lent his voice to the Disney XD series Star Wars Rebels. Next up, he’ll appear in the Peacock Punky Brewster reboot, set for February 2021.

Prinze is still married to Sarah Michelle Gellar, who also appeared in the Scooby-Doo movies with him as Daphne — and had a small cameo in She’s All That! They have two children.

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Jodi Lyn O’Keefe (Taylor Vaughan)

Since playing Zack’s mega-popular (and eventually, mega-dumped) ex-girlfriend, O’Keefe has appeared in a long list of different television shows, including Prison Break, The Vampire Diaries and VH1 sports-drama series Hit The Floor.

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Matthew Lillard (Brock Hudson)

After his turn as the wild reality star who stole Zack’s popular girlfriend, Lillard went on to star in the Scooby-Doo films with Prinze, as Shaggy. He continues to be involved as Shaggy, voicing many Scooby-Doo animated films. Lillard made his directorial debut with the 2012 drama Fat Kid Rules the World, and most recently appeared on NBC’s Good Girls. 

He is married with three children.

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Gabrielle Union (Katie Darlingson)

Since making her big-screen debut as popular girl Katie in She’s All That, Union has gone on to become one of the most famous faces in Hollywood. Her breakthrough role came in Bring It On in 2000, and since then she has landed many different film gigs. In the world of TV, she has starred in the series Being Mary Jane and L.A.’s Finest. On top of that, she is known for her strong activism, specifically as an advocate for sexual assault survivors.

In late 2018, she welcome her first child, a daughter, with NBA star husband Dwyane Wade.

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Dulé Hill (Preston)

After his turn as one of Zack’s pals in She’s All That, Hill went on to star on The West Wing for all seven seasons, followed by Psych, Doubt and Ballers. He currently appears on the series Black Monday.

He is married to actress Jazmyn Simon, with whom he has one son.

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Anna Paquin (Mackenzie Siler)

Since playing Zack’s little sister, Oscar winner Paquin has had a strong career in TV and film. After being among the X-Men as mutant Rogue in the film series, she starred in the HBO hit True Blood. Her role as Sookie Stackhouse garnered her a Golden Globe Award for Best TV Actress in 2009. She currently stars on the Amazon series Flack.

She is married to actor Stephen Moyer, and they have twin sons, born in 2012.

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Kieran Culkin (Simon Boggs)

Macaulay Culkin’s little brother played Laney’s little brother, and eventually made a name for himself in Hollywood. Back in 2002, he was nominated for a Golden Globe for his appearance in the film Igby Goes Down. More recently, he starred in season 2 of Fargo, and is a standout as one of the Roy children on HBO’s Succession.

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Elden Henson (Jesse Jackson)

Of late, Henson — who played Laney’s protective, encouraging friend Jesse — is best recognized for his role in the Marvel Cinematic Universe TV shows as Foggy Nelson, as well as appearances in the first two Hunger Games films as Pollux.

He was married from 2014 to 2016, but divorced from his wife. They share one child together.

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Clea DuVall (Misty)

In the 20-plus years since playing mean art student Misty, DuVall has made consistent appearances in both film and television. She landed roles in the acclaimed film Argo and appeared in television shows such as Heroes and The Lizzie Borden Chronicles, where she portrayed Emma Borden. She also had recurring roles on Veep and The Handmaid’s Tale. 

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Kimberly ‘Lil’ Kim’ Jones (Alex Sawyer)

Now best known as her stage name Lil’ Kim, Jones’ rap career has blown up since she appeared as one of the popular girls in She’s All That. With millions of album copies sold, she is considered one of the greatest female rappers ever.

In 2005, she served a year-long prison sentence for lying to a federal grand jury. She has one child, a daughter named Royal Reign, born in 2014.

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Usher (as Usher Raymond)

Already a household name, Usher played the resident high school D.J. in the film. He’s acted quite a bit since, though music has been his forte; since She’s All That, he’s released six albums (with a seventh on the way) and mentored on The Voice.

Already a father of two, Usher is expecting a fourth child this year with girlfriend Jenn Goicoechea.

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Paul Walker (Dean Sampson)

Walker was on a roll with teen movies — Pleasantville, Varsity Blues and The Skulls — when he took on the role of Zack’s backstabbing pal Dean in She’s All That. He went on to star in the Fast and the Furious franchise, in addition to a handful of other thrillers. 

Walker tragically died in a car accident in 2013. He is survived by a daughter, Willow.

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