Starring Tom Cruise,
Bryan Brown, and Elizabeth Shue, Cocktail was released
in 1988. Probably better categorized as a romantic
comedy, we went ahead and included it here. After
leaving the army, Brian Flanagan (Cruise) moves to NYC,
starts going to college, and works as a bartender (under
the tutelage of Doug Coughlin, played by Brown).
Brown advises Brian to try and find himself a sugar
mama, which he does, bouncing around between the ladies
and eventually settling on Shue.