Entertainment Movies Leonardo DiCaprio's Unconventional Younger Years in Photos How this "overly ambitious, slightly annoying 13-year-old kid" grew up to be the Oscar winner he is today By Diana Pearl Published on November 11, 2019 11:45 AM Share Tweet Pin Email Trending Videos 01 of 09 Late 1970s Gianfranco Gasparro/Liaison/Getty Leo's baby face doesn't get much more adorable than this! Here, he poses with stepbrother Adam Ferrer in Los Angeles back in his single-digit days. 02 of 09 1990 Theo Westenberger/NBCU Photo Bank/Getty Now, he's best known as a film actor, but the world first got to know DiCaprio on the small screen, starting with the short-lived sitcom Parenthood. 03 of 09 1991 ABC Photo Archives/ABC/Getty When he was 17 years old, DiCaprio guest-starred on Growing Pains as Luke Brower, a homeless teen taken in by the Seaver family. 04 of 09 1993 Moviestore/REX/Shutterstock Leo's first big-time, big-screen role came in 1993, when he played a teenager with an abusive father (Robert DeNiro) in This Boy's Life. 05 of 09 1993 SNAP/REX/Shutterstock It was DiCaprio's next film, What's Eating Gilbert Grape, that gave him a taste of awards show glory: He received his first Oscar nomination for the movie. 06 of 09 1994 BEI/BEI/Shutterstock What's Eating Gilbert Grape also earned Leo his first Golden Globe nomination in 1994 and kickstarted a long-standing DiCaprio award show tradition: bringing his mom, Irmelin, as a date. 07 of 09 1993 Yoshi O'Hara/Shooting Star DiCaprio's big break into show biz gave the world priceless, brooding young Leo headshots like these. 08 of 09 1998 Barry Roberts/BEImages He may have already had an Oscar nomination under his belt, but it took until 1997 for Leo to hit superstardom with the ultra-successful Titanic. He attended the Golden Globes with costar Kate Winslet in 1998. 09 of 09 2000 Scott Myers/REX/Shutterstock Leo's bond with his parents, George and Irmelin, held strong as his star rose: here, they share a toast at the London premiere of his film The Beach.