She's All That - Cast

Cast

• Freddie Prinze, Jr. as Zachary "Zack" Siler: An All-American soccer player and the school team captain, the class president, an honor student with the 4th highest GPA, and the son from a prestigious affluent family, the charismatic senior is practically the de facto king of Harrison High School. He is undecided about his future despite already received acceptance from multiple Ivy League universities because he feels that his future has been dictated too much by his parents. After his prima donna girlfriend Taylor ditches him over a faded reality TV star, his legacy as the most popular boy in school is at risk of being embarrassed. In response he boasts to his friends that Taylor is "totally replaceable" because he can find "rebound skank" in any girl and turn her into the prom queen in just six weeks. When Dean picks out Laney as the target, he shows reluctance as she is typically considered to be an impossible character, but accepts the challenge anyway because he is too proud to back out on a wager. Being rejected outright at the start, he manages to successfully approach Laney under the pretense of needing her help with an art independent study. He initially treats her only as a "project", but gradually develops true feeling after discovering the beauty hidden under her wallflower guise. This gets complicated after Dean deliberately reveals the bet, forcing Zack to admit partaking in front of Laney, who out of anger refuses to talk to him again. He wins the Prom King title undisputed, but misses the rest of the prom after rushing off to intervene with Dean's sinister motive on Laney. He eventually catches up to Laney at her home to confess his feelings, and wins over her heart. Because Laney did not win the prom queen, he loses the bet and goes to his graduation ceremony naked as per its terms.
• Rachael Leigh Cook as Laney Boggs: A bohemianistic, bespectacled, redheaded art student and the stereotypical loner geek girl, who prefers to stay in her own home basement painting by herself. Her mom died of leukaemia when she was young, and she has taken over the role of the lady of the house, spending all her spare time homemaking for her father and brother, working part-time at a kebab restaurant and participating in a minority performance art group. She always wears a pair of paint-stained overall and shoes to school, earning her the nickname "Splatter Girl". Though artistically talented, the liberal-minded Laney is oblivious to popular fashion and prefers to focus her artworks on darker subjects inspired by her interest in world affairs. Practically a social contrarian, she is skeptical to approaches by boys, and carries an air horn for self-protection against potential sexual harassments. Regarded by others as "scary and inaccessible", Dean deliberately chooses her as the target of Zack's bet. Initially very annoyed of Zack's "stalking", she starts to warm up to him after being impressed by his improvised on-stage art performance under pressure at Jester Theater, and the mutual feeling between them begins to strengthen after she gradually opens up. Despite her natural beauty, she only emerges out of her shell after Zack and Mac's makeover, and her popularity in school soars almost immediately afterwards as the average non-hotshot students begin to identify more and more with her. As the dark horse contestant, she loses to Taylor at the prom with narrow margins, but emerges as the uncrowned queen in reality. Despite furious at Zack after learning about the bet, she eventually forgives him and makes good of their relationship.

(The name "Laney Boggs" is reportedly a homage to the characters of Lelaina "Laney" Pierce from Reality Bites and Kim Boggs from Edward Scissorhands — an apparent nod to Rachael Leigh Cook's physical resemblance to Winona Ryder.)

• Paul Walker as Dean Sampson, Jr.: Zack's closest pal (together with Preston) and soccer teammate in high school. He appears as a typical jock but is later also shown to be a total jerk with promiscuous interests, and deep down holds a jealous grudge against Zack. When Zack is dumped by Taylor, he takes the opportunity to challenge Zack to a bet about turning any girl into the prom queen. Determined to create one contest that Zack will lose, he picks out Laney as the target after seeing the unpopular "Super Freak" clumsily tripping over a stairway in the schoolyard. When Laney's (and hence Zack's) winning odds becomes prominent, he tries to ruin Zack and Laney's relationship by first revealing the bet in front of Laney, then by trying to seduce and advance on her after the prom, only to be deterred when the ever-vigilant Laney stuns him with her foghorn-loud personal alarm. At the graduation ceremony, he still has trouble hearing.
• Jodi Lyn O'Keefe as Taylor Vaughan: The most popular girl at school and universally regarded as the Prom Queen by default, this wealthy and voluptuous diva is shown as bossy, superficial, flirty, arrogant and rude. She breaks up with Zack after meeting Brock Hudson on her spring break vacation in Daytona, Florida, only to be dumped by Brock later on. When she then wants to rekindle with Zack, she faces setback due to Zack's new-found chemistry with Laney. Her rivalry with Laney surfaces after she openly humiliates Laney at Preston's house party by pouring drink down her dress and insulting her modest upbringing. After Laney's new popularity gives her a run for her money, she eventually wins the prom queen competition with a very close vote, but has the teachers disconnecting her microphone when she begins a vitriolic winning speech towards those who did not vote for her. At the end of the movie, she is seen sitting and smoking alone in the back row at the graduation, presumably her friends all leaving her after finally having had enough of her snotty behavior.
• Matthew Lillard as Brock Hudson: An egocentric, narcissistic reality television star from The Real World, whose career has faded after being evicted from the show. Taylor breaks up with Zack after meeting him on vacation in Daytona. Eventually he breaks up with her heartlessly after he is hired to be in All Stars Road Rules.

(The character is based on the real-world character of Puck from the show's third season.)

• Anna Paquin as Mackenzie "Mac" Siler: Zack's little sister and an amateur fashion expert, who is responsible for Laney's makeover. When Zack is at a loss at the beginning about what to do with Laney and the bet, she suggests to him to "make a little effort" in getting to know Laney better. She is an honest average teenage girl, shown to be a bit boy-crazy, and attends an all-girls school. At the end of the film, she befriends Laney's best friend Jesse because they have similar interests.
• Kieran Culkin as Simon Boggs: Laney's little brother, who admires Zack. He helps out his father's business part-time and works in the school cafeteria as a casual waiting staff. He is shown to wear hearing aids, love Sega, and used to be pushed around by bullies until Zack stands up for him. He also works to help advance Zack and Laney's relationship.
• Kevin Pollak as Wayne Boggs: Laney and Simon's dad, a widowed tradesman who runs his own pool-cleaning business "Dr. Pool". He is a keen fan of Jeopardy! although extremely bad at it. A man of humble background, he is proud of the fact that as a single parent he managed to raise two decent children all through his own hard work, and affectionately calls his daughter "Pumpkin-nose". He is well aware of Laney's relationship issues and encourages her to stop denying good things happening to her.
• Elden Henson as Jesse Jackson: Laney's best and only friend before Zack comes along. An honor student (as seen on his graduation regalia) and a stereotypical nerd with a craving for snacks, Jesse is often scorned by Laney to lose weight before graduation. It is implied that Laney previously beats him in a fight during 3rd Grade but they have become friends ever since. He cares about Laney a lot, and is the first person to assist Zack in approaching Laney by lending Zack his theater ticket for the Jester performance. He befriends Zack's younger sister Mac at the prom because they have similar musical tastes.
• Dulé Hill as Preston: Zack's the other best friend in school beside Dean. He is often the voice of reason in the group and has tried to stop the bet between Zack and Dean, as he believes Dean is taking advantage of Zack's vulnerable situation. Despite being the son of a wealthy owner of the local Ford dealership, he is friendly towards Laney from the very beginning. He seems to date Alex at first but then is later seen at the prom with Katie. Both of them appears to care passionately about Laney's relationship with Zack. After hearing Dean's intention towards Laney, he scorns Dean and predicts his plan a failure.
• Gabrielle Union as Katarina "Katie" Darlingson: Seen first as one of Taylor's best friends, she eventually becomes close to Laney after their first meeting at the beach. She is the only one out of Taylor's clique who is genuinely nice to everyone, speaks honestly, and doesn't always just say what Taylor wants to hear. She nominates Laney for Prom Queen, and is the first person from Taylor's camp to openly switch allegiance, standing behind Laney during their campaign walk. She is seen as Preston's date at the prom, implying they have started a relationship. Both of them are seen arguing over how to help out Laney and Zack, and are visibly disappointed when Taylor is ultimately crowned Prom Queen.
• Lil' Kim as Alex Chasen Sawyer: One of Taylor's friend. She seems to be on friendly terms with Laney even after Laney is nominated for Prom Queen (though she is seen walking with Taylor when the two opposing camps run into each other in the hall). She initially appears to be Preston's girlfriend, but later on attend the prom with someone else.
• Tamara Mello as Chandler: One of Taylor's friend, who does not like Laney. She is shown to be the most loyal towards Taylor, but most likely also grows distant from Taylor at the end as she appears rather apathetic when applauding Taylor's prom victory.
• Usher Raymond as Campus DJ: The cool, smooth PA announcer of the school who knows all the dirty and latest gossips at school.
• Tim Matheson as Harlan Siler: Zack and Mac's father. A Dartmouth alumnus, he wants Zack to go to Dartmouth just like he did, and once made Zack wear a Dartmouth sweatshirt at just five years of age — an emblematic memory that causes Zack great annoyance for not being in charge of his own future.
• Patricia Charbonneau as Lois Siler: Zack and Mac's mother.
• Debbi Morgan as Ms. Rousseau: Laney's art teacher, who values her talent greatly but tried unsuccessfully for four years to get Laney to open up and inject more personality into her work. After Laney paints a picture of her mother as the final project, Ms. Rousseau finds it extremely moving and makes highly positive reference for Laney to all her preferred art schools. At the prom, she tells Laney to hold onto whatever responsible for the transformation, unintentionally makes Laney realize that she should give Zack another chance.
• Clea DuVall as Misty: A gothic-looking student from Laney's art class. She comes from a rich family and has scholarship offer from her first-choice art schools. She and her friend Savannah are mean towards Laney, and once tell her to consider suicide because infamous artists only become appreciated after death. She gets drunk at Preston's party and still behaves condescendingly before passing out, and Laney paints her face into a clown as payback.
• Katharine Towne as Savannah: Misty's friend, who together with Misty are the bullies in art class. They once ask Laney to consider killing herself in order to achieve posthumous recognition of her talent.
• Alexis Arquette as Mitch: Laney's fellow art performer at Jester's theater, known to Zack as "the underwear guy".
• Dave Buzzotta as Jeffrey Munge Rylander: A school bully who wears a T-shirt that says "Kill All Artists". Together with his sidekick Rutley, he tries to humiliate Simon by forcing him to read a porn magazine while calling it Simon's mother, but is forced to share Rutley's pube-laced pizza when Zack intervenes. He is seen dancing with a blow-up doll at the prom.
• Chris Owen as Derek Funkhouser Rutley: A school bully who, together with his partner Rylander, tries to lace a pizza carried by Simon with pubic hair, but is forced to eat his own work after Zack intervenes. He is also shown to photobomb other people at the prom.
• Michael Milhoan as Principal Stickley: The headmaster at William Henry Harrison High School.
• Carlos Jacott as Prom Photographer
• Ashlee Levitch as Melissa
• Vanessa Lee Chester as Melissa's Friend
• Milo Ventimiglia as Soccer Player
• Brandon Mychal Smith as JV Cleaning Boy
• Takbir Bashir as Rapper #1
• Amon Bourne as Rapper #2
• Anthony Rivera as Rapper #3
• Wendy Fowler as Harmony
• Flex Alexander as Kadeem
• Charlie Dell as Man in Falafel Barn
• Sarah Michelle Gellar as Girl in Cafeteria (silent cameo)