After going through the entire Batman retrospective, the boys were looking for a different kind of retro for a follow-up. With no Scorsese and only a few DiCaprio films in their resume from the Aftertaste years, it was decided that their next venture would be the film team-ups of Leonardo DiCaprio and Martin Scorsese.

Much like the boys were at the end of last year, the careers of Scorsese and DiCaprio were at a crossroads in the early 2000s. The veteran director was in dire need of a hit, and the superstar actor was trying hard to shed the sheen of Titanic and move on with his career. So, Scorsese dusted off a script he had been working on called Gangs of New York, and the Weinsteins were happy to finance it, as long as DiCaprio and Cameron Diaz were cast. But were those the only compromises the director needed to make?

Join Garrett, Matt, and the returning (Jeopardy contestant) Michael Guarnieri as they start their look at the five films in this retrospective, and answer the question of whether Gangs of New York was worth Scorsese’s nearly 30 year wait to get it made.