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.