Cocktail (1988)

Brian Flanagan (Tom Cruise) wants a high-paying marketing job, but needs a business degree first. Working as a bartender to pay for college, Flanagan is mentored by his veteran boss, Doug Coughlin (Bryan Brown). Together, their showy tricks and charisma command large crowds and tip payments -- until Flanagan and the cynical Coughlin have a falling out. Flanagan moves to Jamaica to raise enough money to open his own bar, where he falls in love with artist Jordan Mooney (Elisabeth Shue).