8. ‘The Departed’ With Bill Simmons and Chris Ryan

HBO and The Ringer’s Bill Simmons is joined by Chris Ryan to revisit and examine the Oscar-winning ‘The Departed,’ directed by Martin Scorsese and starring Matt Damon and Leonardo DiCaprio. They break down everything from who was in the original intended cast to the film's most memorable moments, as well as what the movie is trying to say about society through DiCaprio’s and Damon’s characters. And, of course, they unpack Jack Nicholson’s memorable Boston accent.