Best known as: Luke on Growing Pains, Jack in Titanic, Romeo in Romeo + Juliet
Golden era: Early ‘90s to present, with a few gaps in between
Then: Mike Seaver who? When Luke showed up on Growing Pains, our pre-pubescent hearts went thump-thump. And he taught us about the dangers of alcohol! Leo could’ve easily succumbed to the “whatever happened to...” syndrome, but he proved his acting chops with What’s Eating Gilbert Grape and Romeo + Juliet. A little flick called Titanic cemented his status as a bankable star.
Now: There was a while when Leo wasn’t bathing, let his fingernails grow to frightening lengths, and saved his urine in milk bottles. No, wait. That was Howard Hughes, whom DiCaprio portrayed in the 2004 film Aviator. In fact, Leo has worked pretty steadily since his heartthrob days and has dated a string of models and even Gossip Girl starlet Blake Lively. He got deeply involved in environmental issues and has also produced several films. He teamed back up with Romeo + Juliet director Baz Luhrmann for a big-screen version of The Great Gatsby, released last year, and is currently up for an Oscar for his critically-acclaimed performance as stockbroker Jordan Belfort in Martin Scorsese's The Wolf of Wall Street.