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| Martin Lawrence | Kevin Caffery |
| Danny DeVito | Max Fairbanks |
| John Leguizamo | Berger |
| Glenne Headly | Gloria |
| Carmen Ejogo | Amber Belhaven |
| Bernie Mac | Uncle Jack |
| Larry Miller | Earl Radburn |
| Nora Dunn | Lutetia Fairbanks |
| Richard Schiff | Walter Greenbaum |
| William Fichtner | Detective Alex Tardio |
| Ana Gasteyer | Ann Marie |
| Sascha Knopf | Tracey Kimberly |
| Siobhan Fallon | Edwina |
| GQ | Shelly Nix |
| Lenny Clarke | Windham |
| Robin Brown | Auctioneer |
| Mike Moyer | Large Man at Auction |
| Darra Herman | Auction Bidder |
| Julie Jirousek | Auction Bidder |
| Kevin Chapman | Bartender |
| Devon Jencks | Officer Keeble |
| Paul O'Brien | Officer Overkraut |
| James Baldwin | Older Tennis Player |
| Jay Carney | Gentleman at Club |
| Matt Seigel | Banquet Host |
| Michael Mulheren | Judge Callahan |
| Michael Jessel | Windham Boy |
| Ryan Hull | Windham Boy |
| Eddie McCabe | Windham Boy |
| Karen MacDonald | Washington Real Estate Agent |
Caffery is a professional thief with taste and style who is trying to rob billionaire tycoon Max Fairbanks' unoccupied beachfront mansion. But in the middle of the robbery, he finds himself face to face with Fairbanks. As Caffery is being arrested, Max sees a ring on Caffery's finger and claims it for himself. It's Caffery's engagement ring, and he's determined to get it back.
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