I love asking people who are really passionate about something to talk about the person or thing they hold up as best. Ask a guitarist, for instance, who the best guitarist of all time was and you’ll get a thoughtful (and probably surprising) explanation and insight into what one artist looks for in another.
Anyway, it was a pleasure to read Roger Ebert explain his 10 greatest films of all time. This is someone who has spent his whole life thinking about a topic and his reasoning behind each choice is deep (outside his odd pick of Tree of Life at the end). I like his explanation of Raging Bull over Taxi Driver for Scorsese:
“Citizen Kane” speaks for itself. “2001: A Space Odyssey” is likewise a stand-along monument, a great visionary leap, unsurpassed in its vision of man and the universe. It was a statement that came at a time which now looks something like the peak of humanity’s technological optimism. Many would choose “Taxi Driver” as Scorsese’s greatest film, but I believe “Raging Bull” is his best and most personal, a film he says in some ways saved his life. It is the greatest cinematic expression of the torture of jealousy–his “Othello.”