Which film marked Martin Scorsese's first collaboration with Leonardo DiCaprio?

Gangs of New York marked Martin Scorsese's first collaboration with Leonardo DiCaprio. The 2002 historical drama stars DiCaprio as Amsterdam Vallon, a young man seeking revenge in Civil War-era New York, opposite Daniel Day-Lewis as the gang leader Bill the Butcher.

The partnership became one of the most productive director-actor collaborations in modern American cinema. After Gangs of New York, DiCaprio and Scorsese worked together on The Aviator, The Departed, Shutter Island, and The Wolf of Wall Street. Their films have ranged from historical drama and biography to crime thriller and dark comedy.

A common mix-up is choosing The Departed, which won Scorsese his first Best Director Oscar, or The Aviator, which followed soon after and earned DiCaprio an Oscar nomination for playing Howard Hughes. Gangs of New York came first, although it was released after the two had already begun developing their working relationship.