Release Date: December 20, 2002

After the underrated Paul Schrader collaboration Bringing Out the Dead, Scorsese tackled a long-gestating dream project: Gangs of New York. Loosely based upon Herbert Asbury's 1928 true crime book of the same name, Gangs was an attempt by one of cinema's poets of organized crime to explore the roots of American gangsterism -- and its inextricable ties with society and government. Set in Civil War-era Manhattan, the movie depicts a city teeming with hatred and violence -- Gangs' Five Points setting is worlds away from the genteel folks living across town in The Age of Innocence. Costing more than $100 million and clocking in at nearly three hours, Gangs of New York can feel overstuffed, and it sometimes lacks historical context, but it's always watchable, thanks to the impeccable production design and a gonzo performance from Daniel Day Lewis.

Leonardo DiCaprio (in his first performance for Scorsese) stars as Amsterdam, the son of Priest Vallon (Liam Neeson), an Irish immigrant gang leader. Vallon is killed in a gang war by Bill "The Butcher" Cutting (Lewis), who leads the virulently anti-immigrant Natives gang. Amsterdam is raised in a home for orphans, but upon his release as a young man, he returns to the Five Points section of New York, where Cutting rules with an iron fist. Amsterdam becomes Cutting's right-hand man, while secretly planning to kill him. Meanwhile in the mayor's office, Boss Tweed schemes to employ the gangs' mutual antipathy to his political advantage. However, forced conscription of Irish immigrants into the Union army threatens to bring New York to a boil. Given that Scorsese had wanted to make this film for decades, his insistence on packing in as many events as possible is understandable, but it can make for a grueling experience. Still, Lewis is mesmerizing to watch, and rarely has a period piece captured an era with such acute attention to detail.

Gangs won Scorsese his first Golden Globe for Best Director, but he couldn't repeat at the Oscars, losing Best Director and Best Picture to The Pianist and Chicago, respectively.