It may not be the most popular of the countless ’90s teen romantic comedies, but She’s All That remains a well-loved fixture in its genre’s history. The R. Lee Fleming film, allegedly ghost-written by none other than M. Night Shyamalan, the 1999 film draws inspiration from George Bernard Shaw’s Pygmalion. Though a fairly loose adaptation of the source material ( in truth it is more akin to My Fair Lady, another Pygmalian adaptation), She’s All That takes a classic and maybe predictable premise and presents it in a modern context for a teen and young adult audience.
One of the most popular boys in his high school, Zack Siler surely thinks he’s all that. So does his girlfriend Taylor, though she dumps the golden boy for a bad boy turned reality star, Brock Hudson. Consumed by vanity and superficial measurements of social success, Zack and his friends theorize that any girl could become as popular as Taylor by simply being his girlfriend. Confident in the weight of his own social capital, Zack readily accepts a cruel bet from his friend Dean: woo an unpopular girl of the latter’s choosing, the romance thus prompting the girl into popularity and culminating in her election as prom queen. Dean chooses Laney Boggs, a quiet and lonely artist that is surprised, and rightfully suspicious, of Zack’s sudden interest. Through observing Laney’s experience introducing herself to his social circle, Zack becomes disillusioned with his peers and ultimately calls off the bet. Dean takes advantage of this to sow discord between the couple, though true love ultimately prevails. The film closes with their graduation, and the audience may assume that Laney and Zack go on to enjoy a healthy romance.
Over twenty-two years after the film’s release, where is the cast today?
Freddie Prinze Jr. / Zack Siler
Miramax films
Fresh off of the success of I Know What You Did Last Summer, Freddie Prinze Jr. enjoyed his first leading role in She’s All That. One of his most notable projects after the hit teen romantic comedy was the Scooby-Doo franchise, in which Prinze appeared in two films as the iconic Fred Jones. Scooby-Doo reunited Prinze with fellow She’s All That star Matthew Lillard, as well as former I Know What You Did Last Summer co-star and future wife, Sarah Michelle Gellar. Gellar and Prinze are still married with two children, with the couple frequently working together throughout their careers. In the late 2000s and early 2010s, Prinze ventured into the world of professional wrestling as a program host, producer, and director.
Rachael Leigh Cook / Laney Boggs
Miramax Films
Starting out as a child star and print model for television commercials and advertisement campaigns, Rachael Leigh Cook began to audition for major acting roles at the age of fourteen. By 1995, the then sixteen-year-old actress landed her debut role in The Babysitter’s Club, her appearance in which opened the doors for a string of increasingly mature roles. After the commercial success of She’s All That, Cooke went on to appear in a number of moderately successful movie and television shows, eventually transitioning into a greater volume of voice acting roles in animated features and video games. Cooke was married for seventeen years to The Vampire Diaries and The Originals star Daniel Gillies, with whom she shares two children. She is the co-founder of Ben’s Sister Productions, a production company she owns with her brother, Ben.
Kieran Culkin / Simon Boggs
The younger brother of Macaulay and Rory, Kieran Culkin launched his career alongside his brother in Home Alone. Kieran Culkin went on to work on several projects as a child and adolescent actor, with the 2000s seeing a marked absence of consistent work and prominent roles for the former child star. Culkin reignited his career recently with a recurring ensemble role in the hit HBO drama Succession. Culkin is married to Jazz Charton, with whom he is raising two kids.
Matthew Lillard / Brock Hudson
After starring in She’s All That as Brock Hudson, Matthew Lillard is the second cast member to have also starred in Scooby-Doo and Scooby-Doo 2: Monsters Unleashed. Lillard’s role as Shaggy has remained a fan favorite throughout the decades, later reprising the character through voice acting in various animated series. He has remained steadily active in Hollywood since, parenting three children with wife Heather Helm.
Related- 10 Actors From the ‘90s Who Aren’t Nearly as Famous as They Used to Be
Paul Walker / Dean Sampson Jr.
The late Paul Walker is largely known and beloved for his role in the Fast and Furious franchise, his death occurring in the midst of filming Fast and Furious 7. Walker got his start as a child actor in the daytime television soap opera The Young and the Restless, followed by lighthearted supporting roles in early adulthood, such as in She’s All That. In 2013, Paul Walker tragically passed away as a result of a single-vehicle car crash, in which he was the passenger. Walker and his friend, Roger Rodas, were speeding on their way from a charity event when the car is concluded to have drifted, resulting in the explosive crash. The 2015 release of Fast and Furious 7 franchise paid tribute to Walker, using his brothers and a great deal of digital effects to complete his character’s story arc. The song “See You Again” was commissioned for the film as a tribute to Walker, with the accompanying music video being the most watched for the month of July 2017. He is survived by his daughter, Meadow Walker.
Jodi Lyn O’Keefe / Taylor Vaughan
After starring as Taylor Vaughan in She’s All That, Jodi Lyn O’Keefe went on to star in minor guest roles in shows like The Big Bang Theory, Two and Half Men, and Boston Legal. The 44-year-old actress has ventured into fashion design, launching her own fashion and jewelry lines, and is a licensed bounty hunter.
Usher Raymond / Campus DJ
Usher launched his career throughout the ’90s, signing deals with major music executives such as LA Reid and Sean Combs. The latter served as co-executive producer for Usher’s debut album. Upon the release of his second album in 1997, the lead single of “You Make Me Wanna…” gave Usher his first gold and platinum hits in the United States. Usher’s career soared from there, becoming one of the biggest faces in R&B in the 2000s. His role as the unnamed campus DJ in She’s All That was a relatively small accomplishment for the musician, who has sold over 80 million records worldwide.
Related- The Best Movies with Singers in the Lead Role, Ranked
Lil’ Kim / Alex Chason Sawyer
Usher was not the only musician to take a role in the 1999 sleeper hit rom-com. Lil Kim makes an appearance as Alex Chason Sawyer, a character whose full name we know on account of her appearance in the film’s closing graduation scene. She appears throughout the film as a member of Taylor Vaughan’s popular posse. By the time Lil’ Kim made her acting debut in She’s All That, she was already one of the biggest names in female rap, maintaining recognition as one of the best female rappers of all time.
Anna Paquin / Mack Siler
Anna Paquin had one of the most incredible debuts of any child actor, earning an Academy Award for Best Supporting Actress at age 11 for her role in the 1993 drama The Piano. Paquin proceeded to enjoy a myriad of carefully selected roles in prominent feature films and television series, including the main character of Sookie Stackhouse in the supernatural vampire drama True Blood. Paquin went on to marry her True Blood co-star Stephen Moyer, with whom she has two biological children and two stepchildren. Having come out as bisexual in 2010, Paquin is an outspoken advocate for LGBT rights.
Dulé Hill / Preston
After his minor role in She’s All That, Dulé Hill went on to star as the personal aide of the president in the hit series West Wing. For 2000s babies, Hill may be most memorable as Sam the Onion Man in the 2003 Disney film Holes. Dulé Hill has further ventured into Broadway, and is married to Ballers co-star Jazmyn Simon.
Gabrielle Union / Katie Darlingson
Gabrielle Union established herself as a staple of 1990s and early 2000s teen films, appearing in the likes of 10 Things I Hate About You, Bring It On, and She’s All That. Union went on to continue her success in movies, though she is also known as an influential social figure through her entrepreneurial work, activism, and authorship. She is currently married to NBA star Dwayne Wade.
