Kathryn and Sebastian, two wealthy, manipulative teenage step-siblings from Manhattan's upper-crust, conspire in Cruel Intentions, a wickedly entertaining tale of seduction and betrayal. The stakes are high when the duo agrees upon a deliciously diabolical wager of sexual conquest without consequences. The pawns? The naive Celcile Caldwell and the virginal Annette Hargrove. Its summer break, and Kathryn has been dumped by her beau, Court Reynolds, for the innocent Cecile. Desperate to get even, Kathryn challenges Sebastian to ruin Celcile by deflowering her and turning her into a tramp-thus humiliating Court by delivering Cecile to him as damaged goods. Sebastian has pretty much 'had' all of the girls in New York City up to this point, and he's gotten a bit bored of it all. Though this is too easy a conquest for him, he obliges. He sets his sights on a greater challenge-the new headmaster's daughter, Annette, who recently wrote an article in Seventeen Magazine about how she intends to stay pure until she marries her boyfriend. Sebastian bets Kathryn that he can seduce the chaste and pristine Annette before school begins in the fall. Kathryn thinks this feat impossible and quickly agrees to the wager. The stakes: if Sebastian succeeds, Kathryn must give him a night of unbridled pleasure, something's he's wanted since their parents got married. If he fails, he must forfeit his priceless 1956 Jaguar to Kathryn and suffer the shame of defeat.

Jerry Maguire (Tom Cruise) is a glossy 35-year-old sports agent working for Sports Management International (SMI). He writes a mission statement about perceived dishonesty in the sports management business, "The Things We Think and Do Not Say: The Future of Our Business." Management sends Bob Sugar (Jay Mohr), Jerry's protégé, to fire him. Jerry and Sugar call all of Jerry's clients to try convincing them not to hire the services of the other. Sugar secures most of Jerry's previous clients. Jerry speaks to Arizona Cardinals wide receiver Rod Tidwell (Cuba Gooding, Jr.), one of his clients who is disgruntled with his contract. Rod tests Jerry's resolve through a very long telephone conversation, culminating in the famed "Show me the money!" scene. Meanwhile, . Frank "Cush" Cushman (Jerry O'Connell), a superstar quarterback prospect from Southern Methodist University expected to be number one in the NFL Draft, also stays with Jerry after he makes a visit to the Cushman home. Leaving the office, Jerry announces that he will start his own agency and asks if anyone is willing to join him, to which only 26-year-old single mother Dorothy Boyd (Renée Zellweger) agrees. Jerry is dropped by Cushman and breaks up with his disgruntled fiancée. He then turns to Dorothy, becoming closer to her young son, Ray (Jonathan Lipnicki), and eventually starts a relationship with her. However, Dorothy contemplates moving to San Diego as she has a secure job offer there. Jerry concentrates all his efforts on Rod, now his only client, who turns out to be very difficult to satisfy. Over the next several months, the two direct harsh criticism towards each other with Rod claiming that Jerry is not trying hard enough to get him a contract while Jerry claims that Rod is not proving himself worthy of the money for which he asks. Jerry marries Dorothy to help them both stay afloat financially and to keep her from moving away. He is emotionally and physically distant during the marriage but is clearly invested in becoming a father to Ray. Although Dorothy loves Jerry, she breaks up with him because she believes that he does not love her. Before the start of a Monday Night Football game between the Cardinals and the Dallas Cowboys, Sugar tries stealing Rod, but Rod and Jerry rebuke him. The two reconcile soon after. Rod plays well but appears to receive a serious injury when catching a touchdown. He recovers, however, and dances for the wildly cheering crowd. Afterwards, Jerry and Rod embrace in front of other athletes and sports agents and show how their relationship has progressed from a strictly business one to a close personal one, which was one of the points Jerry made in his mission statement. Jerry then flies back home to meet Dorothy. He walks in and, in front of her friends, says "Hello." He then speaks for several minutes, telling her that he loves her and wants her in his life, ending with the statement, "You complete me." Dorothy's reply to Jerry is, "You had me at 'hello.'" Rod later appears on Roy Firestone's sports show. Unbeknownst to him, Jerry has secured him an $11.2 million contract with the Cardinals allowing him to finish his pro football career in Arizona. The visibly emotional Rod proceeds to thank everyone and extends warm gratitude to Jerry. Jerry speaks with several other pro athletes, some of whom have read his earlier mission statement and respect his work with Rod. The film ends with Jerry, Dorothy, and Ray walking in the park and stumbling across a Little League Baseball game. When the ball lands near them, Ray throws it back. A surprised Jerry then comments on his natural throwing ability (and possible future in sports), much to Dorothy's dismay.