16. The Beach, “Richard” (2000)
Playing the role of a misguided traveler in search of serenity on a strange island, Leo’s work in The Beach has gone somewhat underappreciated. His character seems simple on the surface, but his mind is complex and rather immature. Critics panned the film on more than one occasion, but it’s another example of the wide range of emotional characters that DiCaprio would come to be known for playing.
Image Source: IMDb