She’s All That’s 1999 release embodied all things ’90s, from campus DJs and poetry slams to choreographed prom dances and girl next door romances.
More than two decades after it hit theaters, fans are still rooting for Laney Boggs (Rachael Leigh Cook) and Zack Siler (Freddie Prinze Jr.) — even after he made a cringey bet with fellow jock Dean Sampson (the late Paul Walker) that he could turn any girl into a prom queen in six weeks.
Cook and Prinze, meanwhile, share a strong connection themselves. “I don’t think that anyone, except for the person who does it with you, can truly understand just what it is to be part of something unless they were exactly by your side when it happened,” Cook exclusively told Us Weekly in August 2020. “So I think we’ll always be bonded in that sense. I hope so at least because he’s such a lovely human.”
Scroll down to see what the rom-com cast has been up to since the late ‘90s:
Freddie Prinze Jr.
Freddie Prinze Jr. followed up his leading role with a series of rom-com films, including Head Over Heels and Summer Catch. He then played Fred in the Scooby-Doo movies before playing Freddie on the short-lived series Freddie, where he also served as producer and writer. The actor appeared on 24 as Cole Ortiz, Star Wars Rebels as Kanan Jarrus and GEGG WARS: Galaxy of Crime as Orak Adalani. He also turned his passion for cooking into a living, releasing the cookbook Back to the Kitchen in 2016. Prinze starred in Christmas With You and The Girl in the Pool and will reprise his role as Ray Bronson in 2025’s I Know What You Did Last Summer.
The L.A. native wed Sarah Michelle Gellar in 2002. The couple share two children, Charlotte and Rocky.
Rachael Leigh Cook
After playing Laney in the hit film, Rachael Leigh Cook starred in Josie and the Pussycats, Tangled and Nancy Drew. The actress had a recurring role on Titan Maximum and Psych before her role on Perception as Kate Moretti. Her more recent roles feature a slew of TV movies, which she also served as producer on, including Frozen in Love, Summer in the Vineyard and A Blue Ridge Mountain Christmas. She also appeared in the 2021 reboot of the rom-com starring Addison Rae, He’s All That. In 2025, Cook starred in Hallmark’s Sisterhood, Inc.
Cook split from husband Daniel Gillies in 2019 after nearly 15 years of marriage. The pair share two children, Charlotte and Theodore. Cook moved on with producer Kevin Mann before she began dating Superman Returns actor Brandon Routh in 2025.
Paul Walker
Paul Walker went from playing the cocky jock Dean to Texas high school quarterback Lance Harbor in Varsity Blues. He then landed the role of Brian O’Conner in The Fast and the Furious, which he reprised in six sequels. The actor was also seen in Eight Below, Flags of Our Fathers, Takers and Hours. In November 2013, Walker was killed in a car accident at the age of 40.
He is survived by daughter Meadow, whom he shares with ex Rebecca Soteros.
Jodi Lyn O’Keefe
Jodi Lyn O’Keefe played mean girl and queen bee Taylor Vaughan in the ‘90s film, while starring on Nash Bridges as Cassidy for six seasons. O’Keefe appeared on The Evidence, Prison Break and Two and a Half Men before portraying Dr. Jo Laughlin on The Vampire Diaries and Lionel Davenport on Hit the Floor.
The actress launched her own clothing line, Queen George Clothing, in 2011 and a year later released a jewelry line. She is also a licensed bounty hunter.
Matthew Lillard
Matthew Lillard portrayed Taylor’s older boyfriend, Brock Hudson, in the teen film. He later reunited with Prinze for two Scooby Doo films and voiced Shaggy in numerous video games before joining the cast of Scooby-Doo! Mystery Incorporated and Be Cool, Scooby-Doo! The actor has also appeared on The Bridge, Bosch and Robot Chicken. He played Dean Boland on Good Girls and reprised the role of Shaggy in 2019 for the Scooby-Doo and Guess Who? series. Lillard has also appeared in Scream 7 and Five Nights at Freddy’s 2.
The Michigan native married Heather Helm in 2000 and they share three children.
Anna Paquin
Oscar winner Anna Paquin played Zack’s little sister Mackenzie “Mac” Siler in the movie. She went on to star in the X-Men franchise as Rogue and landed roles in Almost Famous, The Romantics and The Irishman. Paquin’s TV credits include True Blood as Sookie Stackhouse, Bellevue as Annie Ryder, The Affair as Joanie Lockhart and Flack as Robyn. She played Mary Ann Broberg on A Friend of the Family in 2022 and starred in 2023’s True Spirit.
In 2010, the actress married True Blood costar Stephen Moyer. The pair welcomed twins, Poppy and Charlie two years later.
Elden Henson
Elden Henson portrayed Laney’s childhood BFF Jesse Jackson the same year he appeared in Idle Hands. The actor was then seen in Cast Away, Manic, Lords of Dogtown, The Hunger Games: Mockingjay films as Pollux and Killers of the Flower Moon. TV-wise, Henson appeared on The Defenders and Daredevil. Henson reprised his role as Fulton Reed on two episodes of The Mighty Ducks: Game Changers before reprising his role as Foggy Nelson on Daredevil: Born Again in 2025.
Henson split from actress Kira Sternbach in 2016 after two years of marriage. The pair share son Dodger.
Dule Hill
Dule Hill played popular teen Preston in the rom-com the same year he landed the role of Charlie Young on The West Wing. He has since appeared in Holes, Whisper and Sleight. TV-wise, Hill has had continued success with roles on Psych (which he also served as producer on from 2009 to 2014), Doubt, Ballers, Suits and Black Monday. The Emmy-nominated star also reprised his role as Burton Guster in three Psych movies before landing the role of Bill Williams in 2021’s The Wonder Years, which aired through 2023. Hill went on to star on Bel-Air in 2024 and Good American Family in 2025.
The New Jersey native and actress Jazmyn Simon tied the knot in 2018. The couple welcomed son Levi in May 2019. Hill is also father of daughter Kennedy from a past relationship.
Gabrielle Union
Fans met Gabrielle Union’s popular kid Katie the same year she played Chastity in 10 Things I Hate About You. The Nebraska native then starred in Bring It On, Bad Boys II, Think Like a Man and Breaking In. TV-wise, Union appeared on City of Angels and Night Stalker before landing the role of Mary Jane Paul on Being Mary Jane and Sydney Burnett on L.A.’s Finest — both of which she also served as an executive producer. In 2019, the actress was also a judge on America’s Got Talent Union has since starred on Truth Be Told in 2023, and appeared in Space Cadet and Riff Riff in 2024..
In 2014, Union married NBA player Dwyane Wade. The pair welcomed their first child, daughter Kaavia, in 2018 via surrogate.
Kevin Pollak
After his role as Laney’s dad Wayne Boggs, Kevin Pollak starred on the short-lived series Work With Me. He then appeared in The Santa Clause 2, The Santa Clause 3: The Escape Clause, The Big Year, War Dogs and Teacher. TV-wise, Pollak had recurring roles on Mom, The Marvelous Mrs. Maisel and Better Things. The San Francisco native both wrote and produced Kevin Pollak’s Chat Show from 2000 to 2015. The comedian published his biography, How I Slept My Way to the Middle, in 2012. Pollak’s most recent credits include playing Lamar on The Neighborhood from 2023 to 2025.
He’s been dating writer and producer Jaime Fox since 2009.
Kieran Culkin
Kieran Culkin played Laney’s little brother, Simon Boggs, the same year he appeared in Music of the Heart and Cider House Rules. He then starred in Paper Man, Scott Pilgrim vs. the World and Wiener-Dog. Culkin played Roman Roy on Succession from 2018 to 2023, winning an Emmy for the role in 2023. He reprised his role as brother Matty Banks in Father of the Bride Part 3 (Ish) in 2020. Culkin won his first Oscar in March 2025 for playing Benji Kaplan in A Real Pain.
Culkin married Jazz Charton in 2013. The pair share daughter Kinsley and son Wilder, whom they welcomed in September 2019 and August 2021, respectively. Their third baby was born in late 2025.
Usher
The musician portrayed Laney and Zack’s high school campus DJ in the film. Usher followed that up with a few TV episodes here and there, including parts on Moesha, Sabrina the Teenage Witch and American Dreams. He played himself in 2019’s Hustlers. The “My Boo” singer released nine studio albums from 1994 to 2024. He joined The Voice as a coach for both season 4 and season 6.
The Grammy winner shares two sons, Naviyd and Usher Raymond V, with his ex-wife, Tameka Foster. In September 2020, he welcomed his first child with girlfriend Jenn Goicoechea. One year later, the couple announced the arrival of their second son, Sire Castrello, who was born in September 2021.
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