Taking on the role of swindling, drug addict/broker Donnie Azoff was no easy feat, especially with Hollywood greats like Martin Scorsese and Leonardo DiCaprio watching from the sidelines. Much has been made of the debauchery, excessive partying, and outright greed portrayed in the flick, but Hill is taking it all in stride — and, he even has some pretty interesting things to say on the matter. Despite his on-camera persona, he's not as wild as he seems.
Your character has some pretty crazy scenes in this movie. Did you feel uncomfortable at all playing out some of that almost-X-rated stuff?
"The thing is, I would have done anything that Marty [Scorsese] asked of me, you know? You feel safe because you know he doesn't make ridiculous movies. His films are wonderful, and they're my favorite films ever. I, of course, felt an enormous sense of safety with working with him."
Did you ever want to geek out at the fact that you were working with one of your heroes?
"You can! And, that's the cool thing. He knows people really look up to him — not in an ego way at all, but he just knew that Goodfellas was my favorite film. We would sit around between takes, and he would start talking about Taxi Driver or something organically if something reminded him of it. And, then, once that door was open, I would just launch into my fan mode. He started it, so I just went for it. It was amazing, and also Rob Reiner was there a lot, which was great. One day, just by circumstance, I got to hang out with Robbie Robertson from The Band and Scorsese and Rob Reiner, and it was one of the greatest days ever. It was so surreal."
Did you read either of the books before you started filming? What was your initial impression of Jordan and Donnie and the Stratton Oakmont bankers?
"I'd read the books a few times when I learned that I was in contention for the part. I couldn't put the books down, and I just couldn't believe that this was actually how they behaved and interacted with people. That, to me, was why it was an interesting story — thinking that there's no way this actually happened. That's what makes the movie a story worth telling, because this is what people did and this is how they got punished for it. That to me is the most interesting part — that they got a slap on the wrist. You know what I mean? That's what's really shocking to me."
Did you find yourself liking or disliking the characters? For many people, Jordan can be very charming and has a way of making you want to believe him when he says he's going to change.
"Well, Donnie is pretty hard to sympathize with. I found him entertaining — if I was at a party with this person, it might be fun, but really more obnoxious than anything else. I had a harder time with that — I can't speak for anybody else, but I had a harder time with figuring out if I would actually be friends with these people. No, I wouldn't, but I find them entertaining to watch. I find lots of characters entertaining to watch that I wouldn't necessarily want to spend my time with."
What was the chemistry between you and Leo when you first met? Were you at all intimidated by his relationship with Martin Scorsese?
"Of course, I was intimidated. The first day of rehearsals I was terrified. The first month was just Scorsese, Leo, and myself in a room, and I was terrified. These guys know each other so well, but what's so great about Leo is that he understands — because he has the same reverence that we all have for Scorsese even though he's made five movies with him. So, he can understand that you would be intimidated and try to make it more comfortable."
Was there a moment where you felt like you could relax?
"Well, I'd say after about three or four weeks I figured I'm probably not gonna get fired, because we've shot enough where they wouldn't want to reshoot all of that with someone else."
After working with Judd Apatow, what's the difference in the improv you're doing on set with this movie?
"It's just that the process of making a comedy and a drama are completely different from one another. When you're in a comedy like 21 Jump Street, you have the responsibility to make the audience laugh every minute or you've failed. With a movie like Moneyball or Wolf of Wall Street, you just have a responsibility to be that character as intricately and authentically as you can. And, that, as an actor, is way more enjoyable. Because you're just getting to be this person, and that's your responsibility."
But, Wolf of Wall Street is hilarious at the same time.
"Well, that was completely different. We're never trying to make a joke. In 21 Jump Street, I'm trying to make a joke throughout the entire film. It's more about the idea of the joke, whereas in a drama you would never think, 'I'm gonna say this for this effect.' You just say this because it's natural in that moment.…But, what's funny is that Scorsese will laugh at things that aren't funny, but that he's just excited about. We'll be doing a heavy scene and he'll laugh — but he has a world-famous laugh, and it's the greatest sound in the entire world."
Both Wolf and True Story, a movie you just filmed, have real-life characters and victims. What was the transition like between those two?
"I think when you're telling a real story you have some responsibility. With Wolf, the names were changed and that was a great relief because these people have families, and they didn't write the books that the characters were based on. That kind of takes the pressure off of me, because I just do what I need to do to make the character pop. True Story was really dark, so doing Wolf and then True Story were two dark characters in a row. I had to do 22 Jump Street afterward just to not be bummed out for a year straight.
True Story is about young kids who got murdered, and it's really heavy stuff, but I find real life fascinating. I think movies should feel as much like documentaries as they can. Real life, and why people treat each other certain ways and why they do the things they do is something I'd like to keep exploring."