On his biggest career regret:
I’ll say it even though you’re here: My biggest regret is not doing Boogie Nights. It was a profound movie of my generation. I can’t imagine anyone but Mark [Wahlberg] in it. When I finally got to see that movie, I just thought it was a masterpiece. It’s ironic that you’re the person asking that question, but it’s true.
On his film he rewatches most often:
Leo said, “I rarely watch any of my films, but if I’m being honest, there’s one that I have watched more than others. It’s The Aviator. That’s simply because it was such a special moment to me. I had worked with Marty [Scorsese] on Gangs of New York, and I’d been toting around a book on Howard Hughes for ten years. I almost did it with Michael Mann, but there was a conflict and I ended up bringing it to Marty. I was thirty. It was the first time as an actor I got to feel implicitly part of the production, rather than just an actor hired to play a role. I felt responsible in a whole new way. I’ve always felt proud and connected to that film as such a key part of my growing up in this industry and taking on a role of a real collaborator for the first time.”