A small-scale imposter / con man, making the rounds in 1950s New York, gets caught up in something much greater than his usual scam and decides to let it ride, if just to see where he winds up. In this case the answer is Italy, gorgeous vestige of the old world with just a few hints of the modern one, where he's tasked with convincing a flippant trust funder to return from a perpetual, fortune-draining holiday. That mission quickly goes by the wayside, just as soon as he realizes how much easier life is in the lap of luxury, and he merely exacerbates said money-letting as the wealthy playboy's new wingman. When things take a turn for the messy, though, his welcome worn thin and nothing to show for it but bittersweet memories, a panicked string of responses sends the entire comfortable lifestyle into a tailspin.

At its root, Ripley is an example of how fear and rejection can press a normally smart, affable person over the brink into monstrosity, a surprise considering the playful tone of the first act. Matt Damon, still fresh from his breakout in 1997's Good Will Hunting, shows great versatility in the leading role (essential for such a complicated character), smoothly masking that twitch in his eye from all but the viewing audience. It's one of those films where you'll feel wrong about your rooting interest, knowing all along that the guy absolutely does not deserve a happy ending, with the final moments serving as your comeuppance.