He studies self-help books and believes that he'll be rich someday, if only he gets that big break. The movie is supposed to be about how he outgrows his materialism, although the closing scenes leave room for enormous doubts about his redemption.
The first part of the movie works the best. That's when Cruise drops out of school, becomes a full-time bartender, makes Brown his best friend and learns to juggle those bottles. In the real world, Cruise and Brown would be fired for their time-wasting grandstanding behind the bar, but in this movie they get hired to work in a fancy disco where they have a fight over a girl and Cruise heads for Jamaica.
There, as elsewhere, his twinkling eyes and friendly smile seem irresistible to the women on the other side of the bar, and he lives in a world of one-night stands. That's made possible by the fact that no one in this movie has ever heard of AIDS, not even the rich female fashion executive (Lisa Banes) who picks Cruise up and takes him back to Manhattan with her.
What do you think? Do you believe a millionaire Manhattan woman executive in her 30s would sleep with a wildly promiscuous bartender she picks up on the beach? Not unless she was seriously drunk. And that's another area this movie knows little about: the actual effects of drinking. Sure, Cruise gets tanked a couple of times and staggers around a little and throws a few punches. But given the premise that he and Brown drink all of the time, shouldn't they be drunk, or hung over, at least most of the time? Not in this fantasy world.
If the film had stuck to the relationship between Cruise and Brown, it might have had a chance. It makes a crucial error when it introduces a love story, involving Cruise and Elisabeth Shue, as a vacationing waitress from New York. They find true love, which is shattered when Shue sees Cruise with the rich Manhattan executive.
After the executive takes Cruise back to New York and tries to turn him into a pampered stud, he realizes his mistake and apologizes to Shue, only to discover, of course, that she is pregnant - and rich.
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