A snobbish investor and a wily street con-artist find their positions reversed as part of a bet by two callous millionaires.

After being discharged from the Army, Brian Flanagan moves back to Queens and takes a job in a bar run by Doug Coughlin, who teaches Brian the fine art of bar-tending. Brian quickly becomes a patron favorite with his flashy drink-mixing style. Brian adopts his mentor’s cynical philosophy on life and goes for the money. He leaves his artist girlfriend Jordan Mooney for Bonnie, a wealthy, high-powered executive. Brian soon must chose between the two, as he evaluates his options.

Terry Noonan returns home to New York’s Hells Kitchen after a ten year absence. He soon hooks up with childhood pal Jackie who is involved in the Irish mob run by his brother Frankie. Terry also rekindles an old flame with Jackie’s sister Kathleen. Soon, however, Terry is torn between his loyalty to his friends and his loyalties to others.

When struggling, out of work actor Michael Dorsey secretly adopts a female alter ego — Dorothy Michaels — in order to land a part in a daytime drama, he unwittingly becomes a feminist icon and ends up in a romantic pickle.