Gangs of New York

Plot by Flixster: Plot: In 1860's lower Manhattan, the Five Points section is a dark, teeming corner of the city known for vice and chaos. Into this frontier of lawlessness arrives the young Irish American, Amsterdam Vallon. Amsterdam is the orphaned son of the slain Priest Vallon--once chief warrior of the Dead Rabbits gang that rallied the Irish immigrants of the Five Points. After 16 years in a "House of Refuge," Amsterdam has returned to the Five Points to hunt down his father's killer. His target is William Cutting (aka "Bill the Butcher") who has since become the merciless new leader of the neighborhood and detests the newly arrived immigrants. Each year, on the anniversary of Priest Vallon's death, the victory is commemorated with a celebration--with invitations handed out by way of the Butcher himself. Amsterdam's plan is clear: to lie in wait and slay his father's killer. While waiting for that night, Amsterdam works his way deep into the Butcher's inner circle, a world of alternating honor and cruelty from which he can only hope to escape. But the closer he gets to Bill, the more he falls under his spell and becomes conflicted--playing the role of the man's surrogate son while keeping the true secret of his past in the shadows. At the same time, Amsterdam meets Jenny Everdeane, an enigmatic pickpocket whose fierce independence fascinates him. When details of her closely linked past with Bill the Butcher emerge, the relationship between the three intensifies. Amsterdam's fight for family honor, freedom and the woman he loves ultimately collides with a pivotal moment in New York and American history: the 1863 Civil War Draft Riots. This uprising, fueled by new Americans like Amsterdam, will have repercussions that will spread through the Five Points to the halls of Government and beyond, and reveal a tenacious spirit in the city that endures.

My take:
One of the scariest and most enigmatic villains I've ever seen: William Cutting aka Bill the Butcher played so convincingly by Daniel Day-Lewis. He killed the priest (Liam Neeson) who started an Irish uprising on his turf, and sixteen years later faces his son (Leonardo DiCaprio), who has conned his way into the Butcher's confidence, much like in The Departed. Still this is watchable mainly for the cruelty and unpredictability of the Butcher.