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Witherspoon had already built up an impressive list of credits when she starred in Legally Blonde as Elle Woods. She made her film debut as a teenager in 1991’s A Man in the Moon and had major roles in 1998’s Pleasantville and 1999’s Election. It was Legally Blonde, however, that launched her as a superstar and cemented her leading-lady status. Witherspoon took Hollywood by storm over the course of the 2000s, starring in the 2002 rom-com Sweet Home Alabama; a 2003 Legally Blonde sequel; 2004’s adaptation of William Makepeace Thackeray’s Vanity Fair; and 2005’s Johnny Cash biopic Walk the Line, a performance that won her an Oscar for Best Actress.
In 2012, she and Bruna Papandrea launched Pacific Standard films, through which Witherspoon has produced a number of projects — mostly female-driven literary adaptations — including 2014’s Wild, for which she received her second Oscar nomination for Best Actress. In 2015, she launched fashion and lifestyle brand Draper James, and earlier this year, she took part in EW’s Beyond Beautiful roundtable conversation. She will appear next in this year’s animated Sing and 2017’s TV adaptation of Liane Moriarty’s Big Little Lies, both of which she will also produce.
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Wilson made his film debut in Wes Anderson’s Bottle Rocket in 1996, reteamed with the director for 1998’s Rushmore, and also appeared in such films as 2000’s My Dog Skip and Charlie’s Angels before he played lovable lawyer Emmett in Legally Blonde. He appeared that same year in another Anderson project, The Royal Tenenbaums, and in addition to starring in films such as Old School, Idiocracy, and Alex and Emma in the 2000s (among others), Wilson had a recurring role on That ‘70s Show as Kelso’s older brother from 2002–2005 and starred on Enlightened from 2011–2013. He currently stars in Cameron Crowe’s new music-themed series, Roadies, on Showtime.
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Coolidge had collected a variety of credits in the ‘90s and was best known for playing Stifler’s mom in 1999’s American Pie when she appeared as Paulette, Elle’s manicurist friend, in Legally Blonde. The hilarious character actress, who is a regular in Christopher Guest’s mockumentaries like Waiting for Guffman and Best in Show, has built up a huge résumé in film and TV since, including roles in A Cinderella Story, Austenland, and all of the American Pie sequels. Since 2012, she has starred on 2 Broke Girls.
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Davis played Elle’s image-obsessed boyfriend Warner soon after his film debut, in 2000’s Tigerland. Since Legally Blonde, he has completed some films roles but worked mostly in television, as a lead actor on What About Brian from 2006–2007 and with recurring roles on Damages and CSI, among other series. He is currently a series regular on The Vampire Diaries, on which he has played Alaric Saltzman since 2009.
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Though she had a few small parts over the course of the late ‘90s, Blair’s breakthrough came in 1999, when she starred in Cruel Intentions (along with Witherspoon). That was two years before she played Elle Woods’ archnemesis-turned-BFF in Legally Blonde, and she has been busy in the 15 years since, appearing in such films as 2002’s raunchy rom-com The Sweetest Thing, the Hellboy superhero franchise, and a string of indies in the later 2000s. In 2016, she played Kris Jenner in The People vs. O.J. Simpson: American Crime Story, and popped up in the films Geezer and Mothers and Daughters.
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Garber is a prolific film, TV, and stage actor who had already built an impressive résumé when he signed on to Legally Blonde as the brilliant but sleazy Professor Callahan. Since then, his film roles have included 2002’s Tuck Everlasting, 2008’s Milk, and 2012’s Argo. He is slated to appear next in 2017’s Kill the Poet and Rebel in the Rye. In television, Garber has racked up a multitude of credits, including his lead role as Jack Bristow on Alias from 2001–2006. He currently stars on Legends of Tomorrow as Dr. Martin Stein, also appearing on The Flash.
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Larter was a model before she got her first major role, in 1999’s Varsity Blues. Soon after, she starred as Clear Rivers in 2000's Final Destination. Since playing am accused murderess and Elle’s Delta Nu sister in Legally Blonde, she has appeared in 2003’s Final Destination 2, 2009’s Obsessed, and two Resident Evil films, Extinction and Afterlife. On television, in addition to a handful of guest roles, she starred on Heroes from 2006–2010 and on Legends in 2014. Next, she will reprise her role as Claire Redfield in 2017’s Resident Evil: The Final Chapter.
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Taylor had an impressive film, TV, and stage résumé before she played Professor Stromwell. Since kicking Elle out of her class and giving her some much-needed words of encouragement at the beauty salon in Legally Blonde, Taylor has had roles in the second and third Spy Kids films, 2008’s Baby Mama, and Disney’s two animated Cinderella sequels. From 1998–2003, Taylor had a role as Judge Roberta Kittleson on The Practice, for which she won an Emmy in 1999, and from 2003–2015, she played Evelyn Harper on Two and a Half Men, for which she was nominated for an Emmy four times.
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Cauffiel played Elle’s sorority sister Margot (whose lucky scrunchie was surely responsible for Elle’s success at Harvard). After Legally Blonde, Cauffiel had stints on The Drew Carey Show and My Name Is Earl, as well as roles in the films White Chicks (2004), Guess Who (2005), and Hoot (2006).
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Since playing Elle’s fellow Delta Nu Serena (whose hair is so now) in Legally Blonde, Ubach has had roles in 2004’s Meet the Fockers, 2005’s Waiting…, and 2011’s Bad Teacher. She has been very active on TV, where she has had voice roles on El Tigre: The Adventures of Manny Rivera, The Spectacular Spider-Man, and Kaijudo, among other animated series. She is currently a series regular on Bravo’s Girlfriends’ Guide to Divorce.
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Before she played the perm-loving Chutney in Legally Blonde, Cardellini was most known for her TV work, starring on the beloved but short-lived Freaks and Geeks and having a short but memorable arc on Boy Meets World. Post-Blonde, she starred as Velma in the live-action Scooby-Doo films and appeared in 2005’s Brokeback Mountain, 2014’s Welcome to Me, and 2015’s Avengers: Age of Ultron. In television, she was part of the main cast of ER from 2003–2009, played one of Don Draper’s many mistresses on Mad Men from 2013–2015, and had voice roles on The Goode Family and Gravity Falls, among other series. She is currently in the cast of Bloodline, Regular Show, and Sanjay and Craig, and she will appear later this year in the film The Founder.
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Welch played Mrs. Windham Vandermark, the murder victim’s ex-wife, in Legally Blonde. A legendary sex symbol for her deerskin-bikini-clad appearance in 1966’s One Million B.C., Welch was highly prolific in the ‘60s and ‘70s — and won a Golden Globe for her performance in The Three Musketeers in 1975 — but took on fewer roles in subsequent decades. Since Legally Blonde, she has appeared on the series American Family and Welcome to the Captain as well as TV movies House of Versace (2013) and The Ultimate Legacy (2015).