14. 'What's Eating Gilbert Grape?' (1993)
In this sharply observed but gently told coming-of-age tale, DiCaprio plays Arnie, the mentally handicapped younger brother of Johnny Depp's titular small-town slacker. The film, based on Peter Hedges' novel, is an offbeat mix of typically quirky elements, and it could have easily been hard to stomach. But the author and director Lasse Hallstrom's affection for these characters shines through. Their greatest asset is the young Leo himself, in his first Oscar-nominated role, bringing great sensitivity and complexity to a part that might have come off as cloying or cynical.