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Di Caprio's debut film role was in the comedic sci-fi horror film Critters 3, in which he played the stepson of an evil landlord, a role that Di Caprio described as "your average, no-depth, standard kid with blond hair." Di Caprio made his big screen breakthrough in 1992, when he 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.

In 1990, Di Caprio got a break on television when he was cast in the short-lived series based on the movie Parenthood.

After Parenthood, Di Caprio had bit parts on several shows, including The New Lassie and Roseanne, as well as a brief stint on the soap opera Santa Barbara, playing the young Mason Capwell.

His involvement in Parenthood and the daily soap earned him a nomination for the Young Artist Award for Best Young Actor in each.

Director Lasse Hallström admitted he was initially looking for a less good-looking actor but finally settled on Di Caprio as he had emerged as "the most observant actor" among all who auditioned.

the film became a critical success, resulting in various accolades for Di Caprio, who was awarded the National Board of Review Award and nominated for both an Academy Award and a Golden Globe for his portrayal.

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