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He next starred in Agnieszka Holland' Total Eclipse, which he co-lead with David Thewlis.The feature is a fictionalized account of the homosexual relationship between Arthur Rimbaud (Di Caprio) and Paul Verlaine (Thewlis).It is a biographical film, in which Di Caprio plays Jim Carroll in his teenage years as a promising high school basketball player and writer who developed an addiction to heroin with his misguided friends.

In 1993, Di Caprio co-starred as the mentally handicapped brother of Johnny Depp's character in What's Eating Gilbert Grape, a comic-tragic odyssey of a dysfunctional Iowa family.

In 1992, Di Caprio was handpicked by Robert De Niro out of 400 young actors to play the lead role in This Boy's Life adapted from Tobias Wolff's memoir of the same name.

He played opposite De Niro, who was acting as his stepfather, and Ellen Barkin as his mother.

That same year, Di Caprio got a break on television when he was cast in Parenthood, a series based on a successful comedy film by the same name.

His works that year earned him two nomination at the Young Artist Award in Best Young Actor in a Daytime Series (Santa Barbara) and Best Young Actor Starring in a New Television Series (Parenthood).