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Also in 2002, DiCaprio appeared in Martin Scorsese's Gangs of New York, a historical film set in the mid-19th century in the Five Points district of New York City.

Director Scorsese initially struggled selling his idea of realizing the film until DiCaprio became interested in playing protagonist Amsterdam Vallon, a young leader of the Irish faction, and thus, Miramax Films got involved with financing the project.

Nonetheless production on the film was plagued by blown-out budgets and producer-director squabbles, resulting in a marathon eight-month shoot and, at US $ 103 million, the most expensive film Scorsese had ever made.

Upon its release, Gangs of New York became a financial and critical success however.

DiCaprio's acting was well-received but remained overshadowed by Daniel Day-Lewis ' performance among most critics.