Michael Felgate is an English auctioneer living in New York City where he manages the Cromwell auction house. He proposes marriage to his girlfriend Gina Vitale, but is disheartened to be turned down. Gina tearfully explains that her father Frank and most of her cousins and uncles are gangsters deeply involved in a Mafia crime family, and she is concerned that Michael will be forced into their world. Michael assures her that he will not let this happen, but barely is their engagement party over before he is unwittingly involved in a money laundering scam, and soon the FBI takes an interest in him.
When one of the money laundering scams at Michael's auction house goes wrong, Gina's cousin Johnny confronts and attacks Michael. Gina takes his gun and fires a warning shot into the ceiling, which ricochets and accidentally kills Johnny. Johnny's father Vito finds out, and he tells Frank he will kill Gina unless Frank kills Michael during his wedding speech. Having grown fond of Michael, Frank confesses what Vito has ordered him to do to Michael and the two of them turn to the FBI in return for protection. The FBI set up an elaborate operation in which Michael's execution will be faked at the wedding reception. Michael is given a hidden recording device and is tasked with trying to record Vito into admitting his criminal activity on tape before he is "executed".
Michael's plan fails, and when Vito realises that his execution is a set-up, he orders Vinnie to kill Michael. Vinnie shoots Gina in what appears to be an accident. Vito is arrested for ordering Michael's execution. As Frank and Michael mourn Gina's apparent death in the back of her ambulance, it is revealed that her death was faked as well, and that Vinnie and Gina were also involved with the FBI as a back-up plan.
Hugh Grant as Michael Felgate
James Caan as Frank Vitale
Jeanne Tripplehorn as Gina Vitale
Burt Young as Vito Graziosi
James Fox as Philip Cromwell
Joe Viterelli as Vinnie D'Agostino
Gerry Becker as FBI Agent Bob Connell
Maddie Corman as Carol
Tony Darrow as Angelo
Paul Lazar as Ritchie Vitale
Tony Sirico as First Risolli Man
Vincent Pastore as Al
Frank Pellegrino as Sante
Scott Thompson as FBI Agent Lewis
John Ventimiglia as Johnny Graziosi
Margaret Devine as Helen
Beatrice Winde as Mrs. Horton
Aida Turturro as Italian Waitress
Joseph R. Gannascoli as Jimmy, Gina's Doorman