Great Sports Betting Movies: She’s All That (1999)

Just before the turn of the century, movie screens were littered with films that starred a fleet of youthful fresh faces, many of whom were known from series on the WB, CW, UPN, and other mid-tier cable networks of the era.

This phenomenon was jump-started by the 1996 slasher film Scream, which starred Courtney Cox (Friends), Neve Campbell (Party of Five), and Matthew Lillard. Scream inspired similar films like I Know What You Did Last Summer (1997), starring Jennifer Love Hewitt, Sarah Michelle Gellar (Buffy the Vampire Slayer), and Freddie Prinze, Jr.

In 1999, a consortium of these fresh faces was called together for a romantic teen comedy titled She’s All That. The cast includes Freddie Prinze Jr., Matthew Lillard, the late Paul Walker, Anna Paquin, Gabrielle Union, former Super Bowl Halftime Show performer Usher, Clea DuVall, and recent Academy Award winner Kieran Culkin.

The film was directed by Robert Iscove, who went on to direct the American Idol movie, From Justin to Kelly, in 2003.

Brief Synopsis

High school hotshot Zack Siler, played by Freddie Prinze Jr., is the local big man on campus. Trouble arises for Zack when his girlfriend Taylor, played by Jodi Lyn O’Keefe, dumps him for a reality-television star played by Matthew Lillard.

In an attempt to revive his popularity, Zack agrees to a bet to gain the trust of Laney Boggs, played by Rachael Leigh Cook. Laney is a nerdy outcast that Zack intends to convert into the school’s next prom queen.

Zack claims that any girl at their high school could be turned into the next prom queen with the right transformation and popularity boost. His friend Dean Sampson, played by Paul Walker, disagrees and accepts the wager.

Betting Elements Of She’s All That

Who Makes The Bet? The central bet is made by Zack and his friend Dean. Zack must successfully turn Laney into the prom queen within six weeks.

What Are The Terms Of The Bet? If Zack can get Dean’s chosen girl (Laney) elected prom queen, he wins. If Zack fails, Dean wins. If Zack loses the bet, his agreed-upon punishment is to graduate nude at the school ceremony. This is a winner-take-all bet, similar to how moneyline odds work, but there is no monetary payout.

Who Wins The Bet? The winner of the bet is ultimately Dean. Laney is nominated for prom queen but does not win. That element of the story was usurped by Laney’s discovery of the wager at a party, leading to a major falling out between her and Zack.
Zack honors the loss of the bet and comedically plays it out at the graduation ceremony at the end of the film.

Sources: She’s All That IMDB Page