After serving in the army, Brian Flanagan (Cruise) arrives in New York City with ambitious dreams, eager to make quick money after bagging a cushy job. However, dreams often shatter, and he has to make do with bartending by night while attending business school by day, with experienced bartender Doug Coughlin (Bryan Brown) teaching him how to flair and impress patrons. After experiencing the high of impressing women and being semi-popular due to his skills, Brian begins to dream bigger, dropping out of business school to eventually open a chain of bars — an impractical decision in favor of pursuing something with a mentor who constantly eggs him to throw caution to the wind while being emotionally insensitive to those around him.
An inevitable falling out occurs between the men, and Brian decides to go to Jamaica to make his dreams come true, where he meets Jordan (Elizabeth Shue), whom he treats rather horribly, but his actions are painted as flawed as opposed to being deliberate transgressions. This is where “Cocktail” feels the most grating, as Brian is intended as a protagonist worth rooting for, but only comes off as an obtuse jerk, incapable of treating women like human beings or introspecting about his innermost desires. This aspect would have worked if the narrative rooted Brian as an antagonistic figure who indulged in morally soulless escapades for the sake of making money — something which Cruise could have embodied perfectly, like that of his shrewd, unhinged character in “Collateral.”
The narrative intent of “Cocktail” only feels more questionable with time, along with its mixed messaging that both condones and chastises moral bankruptcy, peppered with a dozen misogynistic jokes and attitudes clogging up an already barebones holiday adventure.
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