Leonardo DiCaprio as Frank Abagnale, Jr. in “Catch Me If You Can” (2002)

To be fair to Leonardo DiCaprio, he was playing a con artist and conned us all about his age in Steven Spielberg’s Catch Me If You Can. The true story followed Frank Abagnale, Jr. over multiple years as he committed identity fraud between the ages of 15 and 21. DiCaprio was 28 when he played the character and was nominated for a Golden Globe for Best Actor in a Motion Picture – Drama.