In a Manhattan cafe, word processor Paul Hackett (Griffin Dunne) meets and talks literature with Marcy (Rosanna Arquette). Later that night, Paul takes a cab to Marcy's downtown apartment. His $20 bill flying out the window during the ride portends the unexpected night he has. He cannot pay for the ride and finds himself in a series of awkward, surreal and life-threatening situations with a colorful cast of characters. He spends the rest of the night trying to return uptown.

Wealthy lawyer Newland Archer (Daniel Day-Lewis) is engaged to sweet socialite May Welland (Winona Ryder) in 1870s New York. On the surface, it is a perfect match. But when May's beautiful cousin Countess Ellen Olenska (Michelle Pfeiffer), who is estranged from her brutish husband, arrives in town, Newland begins to question the meaning of passion and love as he desperately pursues a relationship with Ellen, even though she has been made a social outcast by Archer's peers.

After her husband dies, Alice (Ellen Burstyn) and her son, Tommy, leave their small New Mexico town for California, where Alice hopes to make it as a singer. Money problems force them to settle in Arizona instead, where Alice takes a job as waitress in a small diner. She intends to stay in Arizona just long enough to make the money needed to head back out on the road, but her plans change when she begins to fall for a rancher named David (Kris Kristofferson).

Former pool hustler "Fast Eddie" Felson (Paul Newman) decides he wants to return to the game by taking a pupil. He meets talented but green Vincent Lauria (Tom Cruise) and proposes a partnership. As they tour pool halls, Eddie teaches Vincent the tricks of scamming, but he eventually grows frustrated with Vincent's showboat antics, leading to an argument and a falling-out. Eddie takes up playing again and soon crosses paths with Vincent as an opponent.