Oz Oseransky (Matthew Perry), a miserable suburban dentist, is terrified when he finds out a former mob hitman from Chicago, Jimmy "The Tulip" Tudeski (Bruce Willis), has moved next door to him. When Oz tells his greedy wife about their new neighbor, she forces him to go to Chicago to sell the hitman’s location to the mobsters he betrayed.
Harry Donovan (Jason Patric) is a talented art forger who accepts one last commission to paint a fake Rembrandt for a generous price. Museum experts can’t tell it’s a phony, nor can the clamoring collectors who are willing to pay a bundle for it. Harry hoped to share a hefty piece of that bundle but instead, he’s on the run across Europe, set up for a murder he did not commit.
The strength and convictions of an idealistic young woman, Valerie Alston (Joanne Whalley), are put to the test when she is selected to sit on a jury at the murder trial of a notorious New York mob boss.
In this passionate, hard-edged story, two unlikely lovers, Clarence Worley (Christian Slater) and Alabama (Patricia Arquette), double-cross the Detroit mob by unwittingly stealing a load of valuable contraband. The couple flees to Los Angeles, where their plan to sell the goods and vanish together forever sets them on a collision course with both gangsters and police.
Ray Dolezal (Willem Dafoe), a small-town sheriff, assumes the identity of a dead man in order to solve a murder. He quickly becomes involved in a complex scheme involving betrayal, international intrigue, and a half-million dollars in cash.
This sequel reunites the three surviving Regulators: Billy the Kid (Emilio Estevez), Josiah “Doc” Scurlock (Kiefer Sutherland), and Chavez y Chavez (Lou Diamond Phillips). Arkansas Dave Rudabaugh (Christian Slater) and two unlikely recruits, a fourteen-and-a-half-year-old orphan named Tom O’Folliard (Balthazar Getty) and a soft-spoken farmer, Hendry William French (Alan Ruck), have now joined the gang. But the West has changed since The Regulators last rode through. Cornered by the ruthless cattle kings and double-crossed by corrupt government officials, Billy the Kid leads the Regulators down a treacherous trail towards Old Mexico… and destiny.