Lt. Daniel Kaffee (Tom Cruise) is a military lawyer defending two U.S. Marines charged with killing a fellow Marine at the Guantanamo Bay Naval Base in Cuba. Although Kaffee is known for seeking plea bargains, a fellow lawyer, Lt. Cdr. JoAnne Galloway (Demi Moore), convinces him that the accused marines were most likely carrying out an order from a commanding officer. Kaffee takes a risk by calling Col. Nathan R. Jessep (Jack Nicholson) to the stand in an effort to uncover the conspiracy.
Hard-as-nails Lily Dillon (Anjelica Huston) works as a swindler for dangerous bookie Bobo (Pat Hingle), probably the only man she fears. Arriving in Los Angeles on “business,” Lily looks up her son, Roy (John Cusack), a small-time con artist content with paltry sleight-of-hand cheats. Roy’s girlfriend, Myra (Annette Bening), looks like an All-American type but is a grifter looking to pull off another big-time con. The convergence of the three hustlers inevitably means trouble for all of them.