A degenerate gambler and his two idiot friends come up with an elaborate plan to pay down their colossal gambling debts by marrying the dysfunctional daughter of an upstart billionaire.
A Florida con man uses the recent death of the long time Congressman from his district, who he just happens to share a last name with, to get elected to his version of paradise, the U.S. Congress, where the money flows from lobbyists.
In New York, Felix, a neurotic news writer who just broke up with his wife, is urged by his chaotic friend Oscar, a sports journalist, to move in with him, but their lifestyles are as different as night and day are, so Felix's ideas about housekeeping soon begin to irritate Oscar.
Aging pals Billy, Paddy, Archie, and Sam have been best friends since childhood. When Billy finally proposes to his much-younger girlfriend, all four friends go to Las Vegas to celebrate the end of Billy's longtime bachelorhood and relive their glory days. However, the four quickly realize that the intervening decades have changed Sin City and tested their friendship in ways they had not imagined.