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5. Catch Me If You Can

Leo starred alongside Academy Award winner Tom Hanks in Steven Spielberg’s 2002 crime drama. Based on a true story, the film followed 18-year old con-artist, Frank Abagnale Jr.(DiCaprio), who forged millions of dollars of fake checks as a pilot, lawyer and doctor. The film was nominated for two Oscars and one Golden Globe in 2003.

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