From the sociopathic, hollowed-out scavenger of Nightcrawler to the desperate, bulked-up brawler in this month’s Southpaw, Jake Gyllenhaal has pushed his body and psyche to the brink, cementing his status as an Oscar front-runner and Hollywood’s most dangerous man.

“Do you actually want to know how many sit-ups I did?” Jake Gyllenhaal asks me. “Are you easing me into the question?”

We’re halfway through dinner at Gracias Madre, a vegan Mexican restaurant in Los Angeles—though neither of us is vegan—and there have been a few interruptions. A table of young women next to us has grown progressively louder throughout the evening, either because of successive margaritas or, more likely, because of proximity to the A-lister.

Gyllenhaal’s sister, Maggie, in town for just the day and also not a vegan, has stopped by unexpectedly, asking whether Jake got her text to meet her here. (He didn’t.) And an unapologetic fan has just arrived tableside asking for a photo, a request Gyllenhaal politely—and almost unsuccessfully—declines. (He: “I’m just doing an interview”; she: “Will you be long?”)

The lingering question—what he discovered about the world during the five months he spent training for Southpaw, a dark drama about a light-heavyweight champ undone by his own brutality and forced to rebuild his life—actually has more to do with Gyllenhaal’s head than with his abs. I’m not asking about sit-ups, at least in part because I already know the answer to that question. One thousand. That was in the morning. There were another 1,000 at night, a factoid repeated ad nauseam in the click-bait stories—jake gyllenhaal is ripped, inside jake gyllenhaal’s insane southpaw transformation, the surprising secret to jake gyllenhaal’s southpaw workout plan—that have accompanied the eye-grabbing film stills floating around online.

The training for Southpaw was savage and transformative. Gyllenhaal is almost unrecognizable as brawler Billy Hope, his body roped by sculpted muscle (itself covered in sweat and blood) and his face contorted in a grotesque, triumphant rictus. Right now, though, three lines crease Gyllenhaal’s forehead. Worry lines, unusually deep given his 34 years. He’s wary of talking about all this—the eight-mile runs that preceded the two-a-day workouts that pushed him so far past his limits on his way to adding 15 pounds of muscle that he sometimes vomited on the floor. He can already see the narrative of body transformation taking shape. Two years ago, he lost 30 pounds for Nightcrawler, to play Louis Bloom, a feral hustler who finds his calling selling accident footage to L.A. news stations. This new role, like that one, has ignited not only early Oscar buzz but also an infotainment-y obsession with Gyllenhaal’s physical makeover, as well as his newfound athletic endurance. A few days before we meet, a clip from The Ellen DeGeneres Show surfaces in which DeGeneres prompts Gyllenhaal to jump rope to raise money for charity. “You’re such a good actor! You jump rope so fast!” DeGeneres says jokingly.

It’s not the kind of ribbing you can imagine Christian Bale playing along with (“Now, exactly what did you binge on to gain that paunch for American Hustle?”), and it’s even harder to imagine Robert De Niro, jump rope in hand, recounting his Raging Bull regimen. Gyllenhaal has never shied away from rigorous training: The five months he spent learning to box for Southpaw are reminiscent of the five months in 2011 he spent immersed in the world of Los Angeles police work in preparation for the 22-day End of Watch shoot—from ride-alongs to shooting practice to fire training (“That’s where you run into a burning building,” he explains). The physical metamorphosis is really just an externalization of a process he goes through for every role.

“I believe that. I really do,” Gyllenhaal says. “But I think we all see what we want to see. If you want to see a guy who has gotten into shape, then that’s what you see. But if you want to see what I feel, I think you have to look a little deeper.”

There’s a pause as Gyllenhaal considers what he’s saying, or maybe how he’s saying it, and then a slight course correction. The point may be better made with the easygoing, sly sense of humor that’s always close at hand. “People have a lot of other shit they have to do that’s more interesting and more important, so I don’t blame them for being like, ‘Oh, wait, how many sit-ups did you have to do?’ Or, ‘Oh, wow, what did you eat to lose that much weight?’ But you’re missing the point. Nightcrawler was ironically about the trouble with that question. It was about why people only look at how much weight you lost, as opposed to what’s at the heart of what you’re doing. In that world, where we just focus on those things, somebody like Lou Bloom thrives. In fact, he rules.”

In 2010, Gyllenhaal stared into the mirror, saw a leading man looking back, and blinked—or so the line on him goes. That was the year that he starred in Love & Other Drugs, the romantic comedy in which he played a frequently undressed pharmaceutical rep, and Prince of Persia, a big-budget sword-and-sandals epic adapted from a video-game series. Neither movie fared well critically or commercially, and since then he’s been making what are referred to in Hollywood as “interesting choices,” chasing drug cartels (End of Watch), kidnappers (the disturbing abduction drama Prisoners), car accidents (Nightcrawler), and—in Denis Villeneuve’s strange and dreamy Enemy—himself through films that offered little in the way of box-office glory and plenty of chances to map out darkness. And if that weren’t enough artistic cred, Gyllenhaal also explored theater, starring in two dramas by the British playwright Nick Payne, If There Is I Haven’t Found It Yet and Constellations, his Broadway debut. This account of his turn toward the bleak and unconventional is so much the accepted wisdom that before he collects me at my hotel for dinner, a friend in New York e-mails, “I hope he picks you up in a shitty Kia . . . just the latest in his bold, unexpected Hollywood choices.”

“People say, ‘You made all these changes in your life, and all your movies seem so different now. I really like the movies you’re making now,'” Gyllenhaal says. “Which implies that they didn’t . . .” There is a knowing smile and a low, mischievous chuckle. In truth, he’s been making dark, interesting movies for a long time, since Donnie Darko in 2001, and wrestling with masculine archetypes in many others: as a gay cowboy in Brokeback Mountain, a marine sniper in Jarhead, even the money-hungry ass man of Love & Other Drugs. It may be Gyllenhaal’s life, more than his movies, that has changed.

“I was trying to figure out a lot of stuff,” he says. He was in his twenties, unsure of his “place in things.” That’s the way he puts it now. He put it more bluntly to David Ayer, the director of End of Watch, as Ayer recounted in a 2012 interview with the entertainment-news website HitFix: “I’m sick of everything,” he recalled Gyllenhaal telling him. “I’m sick of my life and I want to change it.”

At a distance, it feels less like a sickness than a search. “We’re all told we’re going to get to a place where those things will come together, where we’ll somehow be whole or happy or whatever it is,” he says. “So I went searching.”

What he hoped to find was collaborative directors, stories that draw on the subconscious, and the chance to work out issues he himself was facing. In Enemy, he plays both a meek college professor and the man’s doppelgänger, a bearded, macho actor with the key to a sex club. The two characters offered him a chance to wrestle with the idea of reconciling intimacy and lust, and, more important, to stage a confrontation with the self at a time when that’s precisely what he was doing in real life.

“I was at a place in my life where I felt totally split,” he says. “I had just moved from Los Angeles to New York.” His sister and her husband, Peter Sarsgaard, live in Brooklyn with their two young daughters. His mother, the screenwriter and director Naomi Foner, also eventually settled in New York following her split from the director Stephen Gyllenhaal after three decades of marriage in 2008. “There’s a period of time in your life, in your twenties, when you’re listening to a lot of other people’s opinions,” Gyllenhaal says. “You’re not sure about what you believe in, and you’re moving in a direction that you feel like looks right to other people. And then you think, Wait, what do I feel? What do I want? What moves me? It’s not always so pure and clear. It’s not like I have my agent on one shoulder and my pure artist on the other.”

If it’s the pure artist who picks me up, he’s driving a very Hollywood car: a white BMW SUV. (“You can write about the car,” he says jokingly, “but it doesn’t belong to me—it’s a friend’s.”) He wears the off-duty actor’s uniform: blue T-shirt, Levi’s, and Nikes, with a blue baseball cap and tortoiseshell shades. During the short ride to Gracias Madre, we discover we are both grandchildren of doctors—his grandmother and grandfather on his mother’s side were physicians—and that both of our grandfathers occasionally wondered when we might get a real job. Neither was exactly kidding.

Gyllenhaal’s maternal grandmother, Ruth Achs, was a pioneering pediatrician who taught at the Downstate Medical Center in Brooklyn. She died at 48, in 1968, 12 years before he was born. But he knew his maternal grandfather, Sam Achs, well. Sam was a surgeon who lived to 94, passing away in January 2014. He was an intensely disciplined man—forever on time, if not early, planning things out months in advance—who awoke at 4 a.m. every day. “My grandfather always wore a bow tie, particularly when he was working,” Gyllenhaal says. “He was really slow in how he would speak, very careful. He saved a lot of lives that way, in that he never would overreact. I didn’t inherit that quality, but I did inherit the discipline.”

Gyllenhaal traces his disciplined work ethic to his father, Stephen, as well. When he was 8 or 9, growing up in Los Angeles, Gyllenhaal would wake up early in the morning and go running with him before school. Stephen was athletic, a top-ranked wrestler in high school in Pennsylvania, but also had an artistic side. “My dad played viola and was also on the football team,” Gyllenhaal says. “He grew up in a small town, very religious, Christian. When he brought a Jewish girl home, it was a very particular thing. But he was Swedish, and so always an adventurer. He’s the guy that says if you’re anywhere near an ocean and you don’t get in, you’re doing yourself a big disservice. And I always feel him. If a storm is about to come, he’s the guy who’s like, ‘Look how big the waves are—let’s get in them for a little bit.'”

That’s the side of Gyllenhaal that has led him to challenging parts requiring intense physical and emotional commitments, including playing the mountaineer Scott Fischer in Baltasar Kormákur’s Everest, opening in September, based on the ill-fated 1996 expedition that claimed the lives of eight climbers. “Balt wanted to make the movie in the real environments,” he says. “I didn’t want to be sitting on a soundstage making some fake movie about Mount Everest, and he didn’t do that.”

That’s putting it mildly. Kormákur shot in IMAX 3D, in Nepal as well as in the Dolomites of northeastern Italy. That’s where Gyllenhaal joined the production in February 2014. “It hadn’t snowed that much in 60 years,” Kormákur says. “There was an avalanche warning every day on the call sheet. It was grueling.” They were filming at elevations of 9,000 to 12,000 feet, in temperatures reaching negative 30 degrees Celsius. “Jake was tough. He went to the limit. It’s all real. His nose was frozen, his beard was frozen, and we were blowing more snow over him, but he wouldn’t give up. And then he wanted to improvise—improvise in minus 30!”

Southpaw’s director, Antoine Fuqua—himself a boxer since 14—saw this fearlessness in Gyllenhaal as well. “He had the will to be in pain and go every day and get punched and train and spar,” he says. For Billy Hope, who spends much of the film “learning that you can’t be a part-time father,” Fuqua knew he had to find a young actor who was in the process of becoming a man. “I thought, Shit, he’s Jake. And nobody else believed me.”

If others couldn’t see what Fuqua saw, it might be because they were looking at the Gyllenhaal of Nightcrawler. “Skinny dude, 147 pounds,” Fuqua says of their first meeting. “I was shocked when I saw him.” (Kormákur concurs: “When he came to rehearsals, he was only half the guy I had hired.”) Fuqua had to find out whether Gyllenhaal could portray a boxer, so he sent him to meet his own trainer, Terry Claybon, at the LB4LB gym in Los Angeles. “Terry called me up and said, ‘Hell no, man. Are you sure you got the right guy?'” Fuqua recalls. “I said, ‘I’m a hundred percent sure. This guy is special.’ When I told Jake to go train, it wasn’t that he was an amazing boxer. He just has desire to do it. He got gutted out. I said, ‘This guy’s got fire in him.’ People just didn’t see it. They’re starting to see it now. Jake is coming out of his shell as a man.”

Part man, part monster. Fuqua would climb into the ring with Gyllenhaal and challenge him toe-to-toe, and unlike World Boxing Association title bouts, their fight sequences didn’t end after 12 rounds. “He was fighting more than a champion boxer would,” Gyllenhaal’s costar Rachel McAdams says. “He was going hundreds of rounds a day to get the shot, day after day.” When Gyllenhaal’s lungs were burning and his arms heavy, Fuqua would ask, “Are you the guy that gives up and sits on the stool and throws in the towel, or are you the one that gets out there and is a fucking beast?”

“Antoine asked me to bring out my animal,” Gyllenhaal says. But Southpaw also offered Gyllenhaal a chance to weigh questions from his life. “[Billy Hope] is me in a lot of ways,” he says. “There are things that I wanted to explore: the idea of what anger is, what it does, if it can be productive. It’s obviously destructive, but is there a way in which you can harness it without rage, so it can actually teach you?”

One thing he learned is how it felt to be hit, how to take a punch and keep going. “They were always playing hardball—there was never any letting up,” says McAdams, who watched Gyllenhaal get pummeled during filming. “I was very worried for him, but I knew he had it under control.”

“I got hit pretty hard in the face,” Gyllenhaal confirms. “All the producers ran [over]. I don’t think out of real worry for me, but just the fact that we were only two weeks into shooting.” He laughs, then continues: “There is something jarring about being hit in the face. I don’t know how to explain it. It wakes me up.” These are lessons most people spend their lives avoiding, but ones that Gyllenhaal sought out. “Your initial instinct is to lean out,” he says. “It’s the instinct to lean in that took me five months. Hitting someone—I don’t have as much of a problem with that.” There’s another low chuckle. “But I don’t like to get hit.”

Near the end of dinner, vegan ice cream ordered, our conversation shifts to an earlier stop on Gyllenhaal’s path to manhood, one with presumably less punching: his bar mitzvah. Though he was raised in a secular household and studied Eastern religions at Columbia University, he celebrated the Jewish rite of passage at 13, albeit in an atypical way. Bar mitzvahs are often lavish affairs; his was not. His family invited his classmates and friends to volunteer at a homeless shelter. The idea, his mother explained, was that “being a good man, if you were going to become a man, was the most important part of it.”

When I bring up this well-circulated bit of Gyllenhaal family history, he deflects. “What does she know?” he says jokingly, then flashes a conspiratorial grin. The serious answer follows. “What else is there but the journey of trying to be a good person, or a good man?” Gyllenhaal asks. “In this incarnation, that seems to be my goal. It’s a complicated thing, because I think the idea of good doesn’t subtract complexities, doesn’t subtract darkness.”

On our way out, we briefly join his sister at her table. The paparazzi have shown up to document the reunion, and with the help of the waitstaff, a departure reminiscent of the Goodfellas Copacabana tracking shot in reverse unfolds: We exit through the kitchen in hopes of leaving privately, to no avail. A cluster of Louis Bloom nightcrawlers await. As Maggie gets into her car and then, moments later, Jake and I climb into the borrowed BMW SUV, the air lights up with camera bursts, and one photographer sidles up to the driver’s side to ask what turns out to be the night’s last question.

“Jake . . . do the ladies like the scruff, or do they prefer clean-shaven?”

Gyllenhaal turns to me, flashes a darker version of that conspiratorial grin, and steps on the gas.

From the August 2015 issue

Gallery Links:
Photoshoots From 2015 > Session 003 [Details Magazine]