Stacy Hamilton (Jennifer Jason Leigh) is a pretty, but inexperienced, teen interested in dating. Given advice by her uninhibited friend, Linda Barrett (Phoebe Cates), Stacy gets trapped in a love triangle with nice guy Mark Ratner (Brian Backer) and his more assured buddy Mike Damone (Robert Romanus). Meanwhile, Stacy’s classmate Jeff Spicoli (Sean Penn), who lives for surfing and being stoned, faces off against Mr. Hand (Ray Walston), a strict teacher who has no time for the slacker’s antics.
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Lane Meyer (John Cusack) is a teen with a peculiar family and a bizarre fixation with his girlfriend, Beth (Amanda Wyss). When Beth dumps Lane, he decides to kill himself, making bumbling attempts at suicide. Outside of his morbid endeavors, Lane spends time with his oddball buddy, Charles (Curtis Armstrong), and befriends Monique (Diane Franklin), a visiting French student. Eventually, Lane resolves to race Beth’s obnoxious new beau on the ski slopes, with unexpected results.
Once a first-rate Secret Service agent, Joe Hallenbeck (Bruce Willis) is now a gruff private investigator whose latest gig is protecting a pole dancer (Halle Berry). When she’s murdered, he grudgingly teams up with her boyfriend, Jimmy Dix (Damon Wayans), an ex-quarterback with a gambling problem, and the two go after her killers. Before long, they stumble onto a plot by a well-known football magnate (Noble Willingham) to bribe federal legislators into legalizing sports gambling.