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The Dream Machine --- The Imagination of the World Wide Web
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Damon, as Tom Ripley, impersonates several other characters besides Dickie Greenleaf - so he ends up playing numerous roles.
Tom Ripley is a highly talented forger and con man. While borrowing a musician's jacket, Tom is hired to go to Europe by Herbert Greenleaf and retrieve his son, Dickie Greenleaf (Jude Law) a rich adult who has no intention of returning to the states. It's an attractive arrangement for Tom Ripley - a trip to Italy, plus a thousand dollars for the errand.
But Dickie has no intention of leaving Italy - or his fiance Marge (Gwyneth Paltrow), so Tom is forced to admit failure and return to New York - Dickie's dad won't send any more money. Unwilling to leave the good life in Europe, Tom kills Dickie and assumes his life. That is, he tells people who have never met Dickie that he is Dickie Greenleaf; meanwhile, he is still Tom to the people who knew Dickie, including Marge. He arranges a suicide note from Dickie, hinting that Tom should get Dickie's inheritance - or at least a good portion of it.
The Talented Mr. Ripley is a clever, intriguing film about a fabulous deceiver, imposter and fraud - which is played by fabulous actor, Matt Damon. The rest of the cast is excellent, also.
I also enjoy movies where the bad guy gets away with everything through quick thinking and brilliant scheming. This type of plot is much more original than the standard bad-guy-gets-caught-and-goes-to-jail story.