After dropping out of high school (SAMOHI) in 1982 to build his acting chops in New York plays, Robert Downey Jr. made his way back to Hollywood and roomed with Kiefer Sutherland while joining the cast of Saturday Night Live along with Anthony Michael Hall. The season was a failure, and almost everyone was fired.

Luckily, within a couple of months, he was cast as James Spader’s sidekick in Tuff Turf and the bully Ian in Weird Science. But his real breakout roles would come 2 years later in The Pick-up Artist & Less Than Zero.