Charlie Sheen – Ferris Bueller’s Day Off (1986)

Dressed in a leather jacket with hair askew and oozing a "too cool for school" attitude, Charlie Sheen's "Boy in the Police Station" cameo in Ferris Bueller's Day Off epitomizes the bad boy fantasy so many of us have. To achieve his stoner juvenile delinquent demeanor, Charlie reportedly stayed awake for 48 hours. Whatever he did, it worked.