Robert Downey Jr. might be one of the most well-respected actors in the world now after turning himself into a major box-office attraction. Through roles in such films as Sherlock Holmes, Marvel’s Iron Man, and The Avengers, Downey has cemented his status as one of the biggest talents of his generation.

Yet his fortunes weren’t always so bright. Plenty of readers will likely remember the Downey Jr. of old, who was even sentenced to federal prison during the 1990s.