Leonardo DiCaprio is still probably best known for his turn as heartthrob Jack Dawson in Titanic, but the role that put him back on the map as an actor after he struggled to find the right projects in the years after that movie's phenomenal success was Gangs of New York, which would be the first of many successful team-ups with director Martin Scorsese. Playing Amsterdam Vallan in the period movie (which co-starred Daniel Day Lewis and Cameron Diaz), Gangs showed Leo in a new light and poised him as the toughest character of his entire career. But Scorsese, who has worked with DiCaprio five times in all (their most recent and arguably best collaboration was The Wolf of Wall Street), never originally sought about the actor for a part in the movie - DiCaprio had to pretty much beg the director to be involved. As he recalls, "As soon as I got the opportunity to finance a movie based on my own name, the only person on that list to be able to work with was Martin Scorsese. So I tracked down the only screenplay I knew had a character for me in it, and that was Gangs of New York.'" Thank God you did, Leo.
