Jonah Hill could still be buying hooker boots at an eBay store right now. A decade ago, with that one-minute scene in The 40-Year-Old Virgin, he launched a career in bro comedies that could have kept him fed like Henry VIII on chronic for years to come. Instead, the party-hearty star of Knocked Up and Superbad went from being confused with his friend Seth Rogen to being acclaimed as the toothiest aide-de-camp in Hollywood. With a set of fake choppers and a thing for quaaludes opposite Leonardo DiCaprio in last year's The Wolf of Wall Street, Hill made his sleazy stockbroker look almost glam. He didn't actually swallow that poor goldfish, but he earned an Oscar nod—and for SAG minimum wage, no less (that's how much he wanted to work with Martin Scorsese). As with his other nominated role, as a numbers-crunching baseball savant opposite Brad Pitt in 2011's Moneyball, Hill turned a sidekick part into a dramatic showcase, an escape from being typecast in dude comedies.

Now 30, Hill is getting wacky again in 22 Jump Street, the sequel to the 2012 action-comedy remake that shocked virtually everyone—save Hill and his producing partners—with its hilarious premium content. The original, also co-starring Channing Tatum, grossed more than $200 million around the world.

Born Jonah Hill Feldstein in Los Angeles on December 20, 1983, Hill never looked much like a movie star. (He's short, with weight that bounces from pudgy to off the charts.) His parents, both from Long Island, moved to L.A. to work on the outskirts of showbiz—his dad is a business manager; his mother did costume design. But it was Hill's big personality that made him popular with his well-heeled classmates at the elite Crossroads School, whose alums include Gwyneth Paltrow, Kate Hudson and Jack Black. In an office not far from there, Hill later joined Judd Apatow's troupe of brilliant misfit clowns for what was merely act one of the actor's career ascendancy. Movies such as Forgetting Sarah Marshall and Get Him to the Greek were fun, but a turnaround came when Hill played a malapropos mama's boy in Cyrus, proving he could really act. Since then it's been A-list all the way for the guy who once dressed as a hot dog and yelled, "Ask me about my wiener!" in a comedy called Accepted.

Contributing Editor David Hochman, who interviewed Zappos CEO Tony Hsieh last month, spent time with Hill in Beverly Hills. "Jonah sometimes comes across on-screen as a laid-back Winnie-the-Pooh type," says Hochman, "but make no mistake—he's intense, shrewd and unrelenting in getting exactly what he wants, and he wants a lot."

PLAYBOY: After the acclaim for The Wolf of Wall Street, why go back and do a goofy comedy sequel like 22 Jump Street?


HILL: I've never made a sequel before, and I didn't think I ever would. But I always say I should be scared of everything I'm doing. If things get too easy, that's a problem. The fear with 22 Jump Street was how to make a good sequel and make fun of ourselves for even attempting to make a sequel. Especially when that sequel is based on a remake of a cheesy 1980s show.

PLAYBOY: What was the solution?

HILL: The solution was to be self-aware from the get-go; 22 Jump Street is a sequel about how ridiculous sequels usually are. Nick Offerman's character says it outright: "Second missions are always bigger and worse than first missions." It's usually just Hollywood people making a cash grab and throwing money around to make it ballsier and louder than the first. By saying that out loud, we're letting people in on what we were thinking behind the scenes.


I spent five years working on the first Jump Street with the writer, Michael Bacall, and the directors, Phil Lord and Chris Miller, and then we had about eight months to start making the second one. It's like what happens with a lot of bands. They have their whole lives to put into that first album, the album's a hit, and then they have to make another one right away. But I think people are going to love this movie.

PLAYBOY: Schmidt and Jenko are now in college—at the age of 30.

HILL: Yeah, they go undercover as freshmen so they can bust up a drug ring at a fraternity. Frankly, a lot of the story is about what I've been going through lately. Many people want to see me as a 24-year-old guy, but I'm 30 and changing a lot. Also, the idea of being in a relationship when things change drastically—that's kind of the big theme of the film. For our characters, it's like they go to college with their hometown honey, and then Channing realizes it's a big wide world out there. Was he with me because we were in a small pond, or does he really dig me? It's a bit of the seven-year itch.


PLAYBOY: You get smacked around quite a bit in this one.

HILL: It's interesting, because before the first Jump Street, I'd never made an action movie. It's such a wild process. You don't just do the scene. You have to wait for things to actually blow up. We were trying to expand this movie to make it bigger, and that's where Channing made a huge difference since he's done so much action before.

PLAYBOY: What was your toughest stunt?

HILL: Hanging from a helicopter or hanging off the side of a moving truck is physically challenging, but just the whole nature of those scenes is intense. When you're standing on a rooftop with a helicopter floating 10 feet above your head, it seems like a bad fucking idea. We were shooting in Puerto Rico that day and heard M16 gunshots, and they weren't coming from us. That's a day I won't forget.


PLAYBOY: You survived.

HILL: I never got hurt, thankfully. The only thing I was in pain from was Channing between scenes. He does this thing where he grabs part of your leg right above your knee. He's one of the strongest human beings on the face of the earth, and when he starts squeezing that pressure point, it's literally incapacitating. It's like being hit by a stun gun, and it gives him nothing but pure evil joy.

PLAYBOY: You've been called "the ultimate wingman." Is that a compliment or a curse?


HILL: I'm sure I could find a way to be offended by that, but it's like anything else. If it's not coming from a close friend or someone in my family, it doesn't mean much to me. If the question is whether it's an insult to be in movies with amazing actors like Leo and Channing and Brad and Michael Cera and all the rest, and supporting what they're doing, then it's a total compliment. I make these movies because I get to work with these people who have become my friends.

PLAYBOY: There's a fearlessness in your approach to acting. You don't hesitate to let it all hang out, whether it's the crack-smoking scene in The Wolf of Wall Street or getting smacked with an octopus in 22 Jump Street. Are you that fearless in real life?

HILL: I think about that all the time, and the answer is no. A lot of actors live their lives like they live their art. As a creative person, you can have no boundaries. I don't live like that. I use my work to get out any of the crazy things I want to do in real life so I can act like a normal person the rest of the time. I get to see what it's like to be a cokehead stockbroker or an undercover cop for six months. I'm lucky. You don't have to go there and ruin your life, but you can still see what someone wants from that sort of experience, what it leads to, what life lessons are to be learned.


PLAYBOY: The Wolf of Wall Street was up for five Academy Awards, including your nomination. Were you shocked when the movie got shut out?

HILL: Not really. Thelma Schoonmaker, who edits all of Scorsese's films and is one of my all-time heroes, wrote me an e-mail the day of the Oscars, saying we probably weren't going to win anything. But she also said the nicest thing, which was that, either way, my performance is going to stand the test of time. That meant so much to me, because this woman cut Raging Bull, Goodfellas and Casino. The Oscars aren't the most reliable measure, when you think about it. The year Goodfellas was nominated, it lost to Dances With Wolves. No disrespect to Dances With Wolves, but which movie do you remember most all these years later? Movies like Goodfellas were the ones that made me want to get into movies in the first place, so how could I be disappointed in any way with The Wolf of Wall Street? I had the best experience I've ever had in my life. I got to work with Leo, who's probably the finest actor of his generation. I know Martin Scorsese. He knows my name. We talk to each other, and he was happy with my performance. I'm an incredibly fortunate guy.

PLAYBOY: You earned $60,000 for the role, but somebody must have slipped you an envelope full of cash afterward, right?


HILL: Nope. Nothing. I just really wanted to do the movie. I said, "I'll take whatever you'll pay me if we can just sign the contract."

PLAYBOY: Did you get to keep the prosthetic schlong from the movie? That scene alone, of you whipping it out and masturbating at a Long Island pool party, makes it a Scorsese classic.

HILL: That was a super crazy scene and hilarious to watch. I had to give that baby back, but I do have my character's teeth in a safe. I usually keep one item from each movie. I have a baseball bat from Moneyball. From Superbad I have the Western shirt my character wore. From Jump Street I have the bike-cop uniform. They're relics of all the crazy good times in my life.


PLAYBOY: Can you pinpoint the moment you became famous?

HILL: The day Superbad came out, Michael Cera and I bought a newspaper. I still have it because it was the day we couldn't walk around together anymore. One day before, we could walk near my apartment in the Fairfax area of Los Angeles and nobody would talk to us. Then all of a sudden it was insane, and it pretty much hasn't stopped.

PLAYBOY: Would you have done anything differently?

HILL: Well, no, but you have to understand that I was young. I was 23 when Superbad came out, and it was just a shock to the system. At this point I've had about seven years to acclimate, but then it was just crazy. Luckily I have the same friends I've had this whole time.


PLAYBOY: You ended up working with many of them repeatedly in Judd Apatow's movies. What was your first meeting with Judd like?

HILL: It was at the audition for The 40-Year-Old Virgin at Universal. It was only for a one-line part, but I was fucking intimidated. I remember I brought my lucky copy of Steve Martin's Cruel Shoes with me, and Judd was like, "Oh shit, that's my favorite book." Then we just started improvising. It was that scene where I'm a customer in an eBay store and just can't understand the concept of an eBay store.

PLAYBOY: For a while it looked as though you weren't going to make any movies without Apatow. Did you feel like a cheating husband when you finally left the Frat Pack?


HILL: If anything, I was fearful to leave and do other things, because that was basically all I knew—Virgin, Knocked Up, Superbad, Sarah Marshall, Funny People. Judd is obviously brilliant, and I owe my career to him, but I realized there are all sorts of other brilliant people out there.

PLAYBOY: Do you think that crew is envious of your success in genres beyond comedy? Is Seth Rogen going, "Hey, why isn't Scorsese calling me?"

HILL: I could not even answer that question. Seriously, everyone I started out with is doing great, and we're all good friends. I think Seth and Evan Goldberg have found what they're brilliant at as filmmakers. Jason Segel is playing David Foster Wallace in a film. Paul Rudd is playing Ant-Man for Marvel. And Michael Cera, that guy is phenomenal. If anything, his greatest achievement is still to come and it's going to be hall of fame. He's just not putting out as much work as the other guys. I think everyone creates his own path.


PLAYBOY: How much of your road to success was calculated effort versus luck?

HILL: It's probably a combination of a ton of factors. I am not the kind of actor who just wanted to do comedy, first of all. But I also didn't want to make just heavy movies. It happened that I had success in comedy early on in my career. Maybe the people watching those movies thought that's all I could do, but I certainly knew I wanted to do more, to try different things.

After Superbad came out, I didn't want to act in a bunch of movies that felt exactly the same, so I wrote some samples and got hired to write for Sacha Baron Cohen. He's a brilliant comedian, and I learned a tremendous amount. I was still getting offered parts similar to Superbad, so I waited, and then Cyrus came along, which changed the course of my career. I knew that was the kind of movie I wanted to do. I just didn't know if people were going to let me do it.


PLAYBOY: Your character in Cyrus is a 20-something kid who's inappropriately close to his hot single mom, played by Marisa Tomei. The movie gets both funny and creepy as Cyrus begins to sabotage her sex life. Is it true you turned down The Hangover to do Cyrus?

HILL: Transformers, The Hangover, yeah. Those films ended up doing incredible things for the people associated with them, but it wasn't where I was headed. Cyrus felt like it really challenged me.

PLAYBOY: Did it hurt turning down the big money?

HILL: I've never done anything for money. And luckily I was young enough and idealistic enough to not think about being a rich guy. I cared so much about the work I was putting out, and it did eventually pay off. Bennett Miller saw an early cut of Cyrus, which is why he cast me in Moneyball. He talks now about what a huge backlash he got for casting me opposite Brad Pitt, since I had done only comedies before. But to Bennett's credit, he stuck with what he believed in and was able to see what I was capable of.


PLAYBOY: Whenever someone gets to a certain level, people inevitably try to cut that person down. Last year you lost your cool during a Rolling Stone interview. Suddenly it was "Jonah Hill's a jerk" and worse. You bristled at inquiries about masturbation, farting and your workout routine, saying, "Being in a funny movie doesn't make me have to answer dumb questions. It has nothing to do with who I am."

HILL: I'd say very clearly I was going through a really hardcore personal experience and I shouldn't have been doing an interview that day. It was combined, I felt, with the reporter not being nice or respectful and I in turn acted unkind and disrespectful, and I regret it. In the future, I probably would just stay home on a day like that.

PLAYBOY: How has fame changed you?

HILL: Every significant event or series of events has an impact on a person's evolution, but I don't view myself as any different from who I was before. The only thing that's embarrassing is if I'm out for one of my friends' or family members' birthday and the attention is on me. But I know how it goes. Growing up out here, whenever I would sit next to an actor I would always get a story out of it. I would need something to tell my friends.


PLAYBOY: What was your life like growing up?

HILL: We had a very inviting house here in L.A. My folks still live there. I would have friends over all the time. I also spent tons of time at my friends' houses. For someone who ends up being an actor, I think the advantage of growing up in Los Angeles is the industry is such a tangible thing. My dad always says that even if you're a dentist out here, you're the dentist to John Travolta or whoever.

PLAYBOY: Your father was the accountant and business manager for Guns N' Roses and other big names. You must have met a ton of celebrities as a kid.


HILL: Not really. I mean, he was the business manager for Cleavon Little, who I was blown away to meet because he was in Blazing Saddles, which I was obsessed with. He came to our house for dinner and I just sat there with my jaw hanging open. He was a really sweet, great guy who, sadly, passed away. But no, I never met Axl Rose as far as I remember. I don't think rock stars really want to hang out with their accountant's kids very much.

PLAYBOY: Your childhood best friend grew up to be a rock star. Did you and Adam Levine have lemonade stands together?

HILL: We did everything kids do. We'd watch movies, play basketball, skateboard around and stuff like that. Listen, Adam was like family, and he still is. His dad and my dad were best friends since junior high and college roommates, and our moms are best friends. We knew Adam had incredible talent. I mean, his voice sounded like it does now when he was 16. He also has a unique voice and clearly was meant to be on stage in front of 20,000 people. But I don't see him as a rock star. He's just a great person to me. It's hard to know what the public perception of someone is once they get famous, but I can tell you this: Adam has been there for me and my family, and his family has been there for my family more than anyone else and, in a deeper way, more than anyone I've ever met in my life. So that guy has all my love and respect forever.


PLAYBOY: Your brother, Jordan Feldstein, is the business manager for Maroon 5 and Robin Thicke, among others. He made news last year when he and Clint Eastwood's daughter Francesca married in Las Vegas and she had the marriage annulled a week later. Then Sharon Osbourne threw a glass of water in his face at an event this past winter. Is he okay?

HILL: I don't want to talk about that, respectfully. I love my family. They're all great. That's all I want to say.

PLAYBOY: Do you think the public and media go too far in prying into celebrities' private lives?


HILL: Here's what I think. You don't know what anyone's like. That's what I've learned the most. You can look from the outside all you want and think you're seeing some sort of truth, but you're never getting the full picture. Leo and I are developing a film from a Vanity Fair article about Richard Jewell that's really about the 24-hour news cycle and how the media killed this guy. It's a heartbreaking story. All Jewell did was save a bunch of people's lives during the Summer Olympic Games in Atlanta, and his life turned upside down. Everybody made him into a hero at first, but then just as fast he was public enemy number one. Watch Tom Brokaw's newscasts from that time or watch Jay Leno. People, without any knowledge, just turned this guy from a security guard doing his job into a terrorist. It was trial by media. And even though he was exonerated, he ended up dying too young from the stress of it all. When you don't know anything and you make judgments, you have the power to ruin somebody's life.

PLAYBOY: Do you ever think about your legacy?

HILL: As I get to the age when I'm thinking about having my own family, I realize I'm going to have to explain scenes from movies like The Wolf of Wall Street to kids, specifically. It's one thing when you're watching somebody else in a Martin Scorsese movie. I got to appreciate his work when I was nine or 10, when some kids were still watching Barney. Not that I'm looking to start a feud in a magazine with Barney. But when it's your own dad snorting cocaine off someone's breasts in a movie, that gets trickier.


PLAYBOY: There are tons of drugs in many of your movies. What's your drug policy behind the scenes?

HILL: If you're an adult over 18, your life is your own. You have to make the choices that are going to define you. No one can make them for you.

PLAYBOY: How much pot do you smoke?

HILL: I don't really smoke now. I have nothing against it; it just doesn't make me feel good. I don't like feeling bad the next day, whether it's from drinking or pot or anything. And I enjoy my days so much more now because of it. In my early 20s I felt like all my weekend days were spent nursing hangovers. Now I have a dog. I like to go to the dog park, get coffee, go to the gym. Channing set me up with his trainer, and I like working out. That takes a lot of stress out for me.


PLAYBOY: When you look at your photos from the past 10 years, your weight is all over the map. How's it going in that department?

HILL: [Laughs in annoyance] That is so ridiculous, man. Would you ever ask someone who wasn't in the public eye, who you just met for the first time, that question? I seriously doubt it. I'm happy with the way I am. I have a good time. I feel healthy. You can ask whatever you want, but my weight is an unimportant part of any discussion about me.

PLAYBOY: It's part of your image, though. At last year's Comedy Central Roast for James Franco, Sarah Silverman joked that you'd gained 50 pounds for your last movie because the producers wanted "a Jonah Hill type."


HILL: You know, you're in a vulnerable position on a night like that. Anything you're insecure about is probably going to be brought up. Some were jokes, some was exaggeration. But again, Sarah doesn't really know me. I mean, Seth Rogen was there and he obviously knows me well. Franco knows me well. Bill Hader knows me well. But even my Hollywood friends, for the most part, don't know me that deeply. So I just have to laugh about it, and it ended up being a really fun night.

PLAYBOY: Do you think Hollywood prefers you looking a certain way? Is a comedy somehow funnier if you're heavier?

HILL: It all depends on what the character is supposed to be like. I would alter myself in any way for a character I really wanted to play. I'm here to put out movies. I do the best I can. I try to stay in shape. That's it. That's all you can do. I don't mean to be difficult, but let's move on.


PLAYBOY: Agreed. What was your first role as an actor?

HILL: In sixth grade they needed an Elvis impersonator in a play, and I got the part. It didn't take a lot of effort, and it got an immediate positive response from a teacher—which was a first for me.

PLAYBOY: You weren't a good student?

HILL: I did okay, but I kind of couldn't handle the idea of following instructions in that way. I knew whatever I ended up doing in life would need to be under my own guidelines. I was a class clown. I just loved to make my friends laugh and to disrupt things. I guess all actors deep down just want attention, and I certainly did. So I figured out pretty early that I could control a room with a well-placed comment or barb. It took all the power away from the teacher. That felt completely thrilling to me.


PLAYBOY: When did you know you wanted to act for real?

HILL: I guess it was a slow progression. Weird shit happens. It dawns on you that real people do this job for a living. I remember my friend and I saw Charlie Sheen at the Avco movie theater in Westwood when we were in junior high or early high school. I loved Charlie's movie Cadence, in which he's on a chain gang in some kind of Army jail situation. Anyway, I don't know what gave me the courage to talk to him, but we just stood there in line talking about that movie and how Major League was one of my favorite films.

I had a few experiences like that that made me think, Okay, these are just people. At the mall in Century City one time, my mom was late picking me up because she'd forgotten about daylight savings time. Happy Gilmore had just come out and I was obsessed with Adam Sandler. Anyway, I'm sitting there waiting for my ride and there's Adam Sandler waiting for his girlfriend, who was also an hour late. He could tell I obviously worshipped him, and he was really cool about it. That's the way Adam is with anyone if you ever see him. He doesn't talk down to people as if he's a big deal and they're not. Those experiences took a lot of the mystery out of the business.


PLAYBOY: What's the story about you making crank phone calls with Dustin Hoffman?

HILL: I knew his kids. I would go over to their house and he'd somehow get me to do it. I did this thing where I called this really seedy hotel during Oscars season, pretending to be Tobey Maguire's assistant. I'd try to convince the owner to do these outlandish things like install a water tank for Tobey's pet seal and shit like that. I can't imagine anything better for your improv-comedy skills.

PLAYBOY: That performance helped you get your first movie role, right?

HILL: Yeah, it's crazy. First of all, Dustin Hoffman is my favorite actor of all time. He represents the ultimate goal of what I would ever try to do, which is be able to succeed in any genre so beautifully. There's no one you can compare to him. It's not like I'm saying I want to be like him. I'll never be as good as he is, but I can try. What was so incredible was Dustin taking a chance on me. I don't know why he did it, but he got me a part in I Heart Huckabees, and that pretty much set me on my way.


PLAYBOY: Knowing what you know now, what advice would you give that 20-year-old version of yourself?

HILL: I spent so much of my time being anxious, so I'd probably say, "Don't stress so much." All through my 20s, I worried too much about things, both having to do with work and not, that ultimately turned out to be unimportant. Am I going to get this job? Is this girl going to text me back? Is my friend mad at me? I used to think everyone was mad at me. That's a big thing I've had to work on in my life.

PLAYBOY: You've spent a lot of time playing college kids. What was college like for you?


HILL: I had two polar opposite experiences before I dropped out. First I went to the University of Colorado Boulder for a semester, which was like a movie cliché of what college is like—football, parties, girls, huge drinking culture. Then I went to the New School in New York, which is your typical artsy school. I know everybody says you can't regret stuff, and I don't. But on reflection, even though I was working during my college years, making Superbad and all those movies, I probably didn't learn as much about myself as I could have. You realize later that the lessons you learn in college are only partly about what you get out of class. High school was about not feeling horrible about myself. How do I cope with my insecurities? It's so awkward. College is about discovering who you are and starting to reinvent yourself. I think if I had continued, I would have known things that took me a few extra years to learn. But again, I was so anxious about so many things at that time, I just thought, Shit, I need to be working.

PLAYBOY: How do you calm down when you're stressed?

HILL: I hang with friends, watch South Park—oh, and definitely listen to Howard Stern every day. I love his perspective on the world, how well he knows himself and also how he's evolved. If you listen to old tapes from the 1990s or 1980s, he's a different man now. His level of thoughtfulness toward who he's interviewing, what he's curious about now versus what he was curious about then. I gave him a compliment last time I was on that I truly meant, which was: Imagine a show being on for 25 years or whatever that only gets better and better as time goes on. That doesn't happen in any other facet of entertainment, but it happened with Howard's show. So listening to Howard helped. [laughs] And therapy.


PLAYBOY: How much therapy have you done?

HILL: A lot. It has probably been one of the most grounding and positive aspects of my entire life. I mean, there's a certain value in having neuroses as an actor, I guess. I work better from a place of thinking I don't deserve to be there, but that helps only to a degree. Therapy gets me recalibrated. It has taught me that every good and bad thing that comes my way is an opportunity to learn. It's gotten me over this idea that I'm responsible for other people's happiness. That mind-set can be crippling in a lot of ways. The best way to take care of people is to be in the best mental and emotional condition you can be in yourself. Honestly, besides family members and a few friends, my relationship with my therapist is the longest relationship I've ever had.

PLAYBOY: Are you a commitment-phobe?

HILL: When I was younger, I always cared more about my friends and having fun than being in a relationship with a woman. Then it's kind of weird when you first become well-known. Certain women become interested in you because of that, though it's easy to discern who wants what. As I matured, my relationships matured. I've always had girlfriends, and I have one now. As I get older I'm more open to the idea of having a family and kids and all that, though I don't think I need to make that decision in the next day or two.


PLAYBOY: By the way, people talk about Leonardo DiCaprio's "pussy posse." Do you have a membership card now?

HILL: [Laughs] Oh, please. That's absurd. Leo's just a great guy. The posse doesn't exist. That's not to say he doesn't get a lot of attention from women. Most women who see him are attracted to him and interested in him, but he handles it beautifully.

PLAYBOY: Have you recovered from the airplane orgy scene you did together in The Wolf of Wall Street?


HILL: The only word I can use to describe it is unhygienic. The women were obviously attractive, but it's an unsexy environment. It doesn't feel like you're hooking up with somebody. It feels like you're at work. The woman who was simulating oral sex on me was talking between takes about picking up her kids from school. And some guy's genitals are in my face in this hot, cramped, sweaty space. Then, months and months later, your mom gets to watch it with you.

PLAYBOY: Did she enjoy being your date at the Oscars?

HILL: She's a Jewish mom at her core, so she had snacks in her purse and was giving them to Sandra Bullock, Julia Roberts and everybody. I think she likes to be the mom in every situation. Leo's mom hung with my mom, and Bradley Cooper's mom was there too. So they had a cool little mom crew going on. If seeing your mom in a situation like that ever seems normal to you, you know you're jaded. To me, it's still totally surreal.


I got to hang out with a lot of cool people that night, like Alfonso CuarĂłn and his director of photography from Gravity. But maybe the greatest moment was when Leo and I got to spend time with Don Rickles. We were at the Paramount pre-Oscars party, and Don was there with the head of Paramount. We basically bum-rushed him because we're both huge fans. The man did not disappoint.

PLAYBOY: Did he call you "hockey puck"?

HILL: Of course! The guy is almost 90 years old and he's still got his game. He laid into Leo really hard because he was wearing a newsboy hat. Don was like, "Hey, yeah, just keep the cab running outside, kid. I'll be out in a minute." Love that guy.


PLAYBOY: What's next for you?

HILL: James Franco and I made a really heavy film together called True Story. It's a true story about this New York Times writer, Michael Finkel, who I play. He was a wunderkind who wrote something like 11 cover stories for The New York Times Magazine by the time he was in his early 30s. Then he got fired for making up a bunch of stuff. A day or two later, he gets a call from someone saying, "What do you think about the murders?" Mike's baffled. Apparently a guy who was accused of killing his wife and kids in Oregon fled to Mexico and was posing as Mike Finkel, and the only person he'll talk to is Mike Finkel. That's James Franco's character, and it's kind of a cat-and-mouse game where you don't know who's using who and who's lying or telling the truth. Mike's trying to get his career back, but it's a tough situation. Mike is not a bad person. I got to know him. What he was doing at that time might not have been the coolest thing—using a family getting murdered in order to write a book to get his career back. But it's a pretty amazing story.

PLAYBOY: Franco is an interesting character. He's turned his life into a kind of performance art.


HILL: I love James. He's so interesting about playing with the perception of who he is. It's like what you see with Shia LaBeouf or Joaquin Phoenix. They go through periods when they put things out there for the public that are open to everyone's interpretation. Actors and directors are idiosyncratic people, but that's why I love the profession so much.

PLAYBOY: Is there anyone you're dying to work with?

HILL: Of course. Todd Field is a director I really love. I'd do just about anything with Paul Thomas Anderson or Spike Jonze. Bennett Miller and I are constantly figuring out what we should be doing together. He's the greatest. I mean, obviously Scorsese is the greatest, but the experience I had with Bennett on Moneyball, the friendship we had, the understanding of what we care about in filmmaking—he's an actual genius. He has a movie coming out this year called Foxcatcher, which is going to change the game. The only other films he's made are Capote and Moneyball, which were incredible films. He's a volcano of talent.


PLAYBOY: Is there any truth to the rumors that you're doing a remake of Bright Lights, Big City?

HILL: None whatsoever. People also tell me I'm going to be in a new version of Ghostbusters, which isn't happening either. It's so easy to spread misinformation.

PLAYBOY: Will there be a 23, 24 and 25 Jump Street?

HILL: I don't know. It might be nice to have a break. The last time I had an actual vacation that lasted longer than a couple of weeks was before the Get Him to the Greek press tour. I mean, thank God, right? I'm the luckiest person to have been working so steadily for so long. But doing another Jump Street sequel would come down to whether it makes sense from a story point of view. The first one felt like it needed a sequel. We barely ended the movie and we were talking about doing a second. College seemed funnier than high school as a setting. There are so many obvious jokes about what we could do in a third one, but whatever we did, it would not be about us going undercover. These characters are great on their own, and we'd want to explore that in any other sequel.


PLAYBOY: What are your all-time favorite sequels?

HILL: I'm not comparing it to our film, obviously, but I think The Godfather: Part II is better than The Godfather. I actually think Back to the Future Part II—and I get so much shit for this—is better than the original. The first one is a masterpiece, but you know what the past was like, and they're just going back to that, which already existed. In the second one, they actually have to create the future. If you look at what it is in the film and then look at Kanye West and all his stuff, you see they literally created an aesthetic for what the future ultimately became. People today dress like Marty McFly in the future—you know, the shoes and the jackets and everything. We're all McFly now. I think the second Austin Powers with Mini-Me stepped things up. Another one everyone gives me shit about, but I don't care, I'll say it: I think Wayne's World 2 with Waynestock is great and better than the original. I just love the Doors references and the self-awareness about the music festival. I could watch that movie over and over.

PLAYBOY: Okay, lightning round. What's the most fun you've had at a party?

HILL: Well, the weirdest party I've ever been to was in Sweden. I went traveling by myself a few years ago, and I was in Stockholm and met some random people who took me to a house party where everyone was dressed up as crazy Vikings and Viking wenches. I was the only one who wasn't dressed up. Everybody ended up singing Viking songs and getting really drunk.


PLAYBOY: Confess your greatest indulgence.

HILL: I spend too much money on watches. They're important to me. You look at them all day, and for me, every time I look at what time it is, I remind myself how hard I've worked to get one of these crazy timepieces. [raises wrist to show a black-and-white watch] This is one I had made for the Oscars by Bamford, a really great company in England that customizes watches. This one has my initials in green, which is my favorite color.

PLAYBOY: Nice. How about your pop culture guilty pleasures?

HILL: Oh gosh. With movies, it has always been Casino, Goodfellas, The Big Lebowski, Rushmore, Three Kings. Whenever those are on, I'll watch them. I'm not sure how guilty it is, but I just watched this incredible documentary series called Brody Stevens: Enjoy It! Comedy Central billed it as its first drama, but it's really kind of a bipolar experience that's quite remarkable. I love any kind of documentary. I loved 12 O'Clock Boys, about this group of inner-city dirt bikers who do crazy shit in Baltimore. I'm watching Narco Cultura tonight because I'm obsessed with the narcoculture scene that's becoming popular around Mexico border towns. Basically, all these young people who aren't drug traffickers dress and act like they are. They have dance clubs where people celebrate narcotics and the cartel culture, the guns, the fashion. I find it disturbing that anyone would want to popularize and glorify any of it, but it's fascinating.


PLAYBOY: One more. Most surreal Hollywood experience?

HILL: Steven Spielberg came to the set of The Wolf of Wall Street and spent the whole day. Spielberg and Scorsese would stand together at the monitor, watching the scene I just acted in. I'd get notes from both of them and go, How the hell did I get here, again? That's something I'll remember when I'm 90 years old.

PLAYBOY: What kind of old guy do you want to be?

HILL: Surrounded by kids and grandkids. But I'm not there yet, you know? I'm happy and just enjoying my life. I'm a few months into my 30s. I'm not going to act like I'm some sage or anything, but for everyone I talk to, their 20s were confusing, and my 20s were very nontraditional. I feel a lot more comfortable with who I am now, and I'm doing only films that I care about. I'll never do another film, knock on wood, that I'm not dying to do and crazy passionate about. I've never had that openness in my career or my life or felt comfortable enough to not just take a job. Honestly, I've never felt so comfortable in my own skin. For me, it's really about doing great and engaging work right now. It comes down to making movies I'd want to watch. So even though Jump Street and, say, Superbad are goofy comedies, I'm as proud of them as I am of Moneyball, The Wolf of Wall Street or Cyrus. Honestly, I just want a stack of DVDs one day that says this is what I spent my 20s and 30s and beyond doing, and these are still the movies I would go see with my friends.


This article was originally published in the June 2014 Issue of Playboy.

Photography by Michael Muller