goes by Laney's house and asks about her mother, who died when Laney was young, and talks about his father, who is pressuring him to go to Dartmouth for college. Zack leans in to kiss Laney but pulls back when she jokes that it is just to get her vote for prom king. The next day, Zack defends Laney's brother, Simon, from bullies in the cafeteria. After a falling out with Zack, Dean asks Laney to be his prom date. Taylor is humiliated when Brock dumps her, so she cozies up to Zack. When Zack turns her down, she tells him that Dean has already asked Laney to the prom. When Zack confronts him, Dean reveals the bet, forcing a public confession from Zack. A furious Laney rushes from the room, refusing to speak to Zack. Unable to reconcile with Laney, Zack takes his sister to the prom. After some persuading from her father, a disheartened Laney agrees to go with Dean. At the dance, Dean boasts of his plan to seduce Laney. Laney's friend Jesse overhears, and he and Mack rush to warn Zack, who has taken the stage with Taylor as Prom King and Queen. Zack rushes after Laney, who has already left with Dean. Laney returns home to find Zack is there. Laney explains how she avoided Dean's advances. Zack confesses his true feelings, and they share a dance and kiss by the pool. Laney asks Zack about the bet, and he says mysteriously he will honor the terms. On the day of graduation he appears onstage nude except for cap and a soccer ball, to applause from the crowd and smiles from Laney. Cast Production Casting The film had an ensemble cast of up-and-coming actors, including Kieran Culkin, Oscar winner Anna Paquin, Jodi Lyn O'Keefe, musician Usher Raymond, Gabrielle Union in her film debut, Dulé Hill, and Lil' Kim. Producer Richard N. Gladstein noted, "There were other films that you could've seen them in, but they weren't usually the leads in those films." According to director Robert Iscove, Miramax co-head Harvey Weinstein was very involved in script development and casting, and was able to get great actors in very small parts as a personal favor. Iscove said Josh Hartnett was considered for the role of Zack Siler, and many actresses were considered for the role of Laney Boggs, including Mena Suvari, Leelee Sobieski, and Jordana Brewster.