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.

In early-1970s Las Vegas, low-level mobster Sam "Ace" Rothstein (Robert De Niro) gets tapped by his bosses to head the Tangiers Casino. At first, he's a great success in the job, but over the years, problems with his loose-cannon enforcer Nicky Santoro (Joe Pesci), his ex-hustler wife Ginger (Sharon Stone), her con-artist ex Lester Diamond (James Woods) and a handful of corrupt politicians put Sam in ever-increasing danger. Martin Scorsese directs this adaptation of Nicholas Pileggi's book.

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.

To take down South Boston's Irish Mafia, the police send in one of their own to infiltrate the underworld, not realizing the syndicate has done likewise. While an undercover cop curries favor with the mob kingpin, a career criminal rises through the police ranks. But both sides soon discover there's a mole among them.