Leonardo DiCaprio and Hollywood's Biggest Directors

What's Eating Gilbert Grape, 1993
Director Lasse Hallström gave DiCaprio the role of Arnie Grape, the mentally challenged younger brother of the title character, played by Johnny Depp. Hallström, acclaimed for his films, My life as a Dog, The Cider House Rules and Chocolat, helped guide 19-year-old DiCaprio to his first Oscar nomination for best supporting actor.

• Top 10 Actor-Director Pairings
• TIME's Movie Covers