Daniel Day-Lewis as Bill in Gangs of New York

Martin Scorsese sent Leonardo DiCaprio to persuade Day-Lewis to play the unforgettable Bill the Butcher. DiCaprio picked him up at Day-Lewis’s house and they walked around for 10 minutes before Leo worked up the courage to finally speak. It wasn’t until later, at a dinner with Leo’s Hollywood pal Tobey Maguire, that Day-Lewis was finally convinced.