Why Jack Antonoff Is a Pop Star Even a Mother Could Love

Jack Antonoff, photographed by Christopher Anderson/Magnum Photos/New York Magazine Photo: Christopher Anderson/Magnum Photos/New York Magazine

“Sorry if I look weird. Am I bleeding from the side of my face?” Jack Antonoff asks, opening the door to his childhood home in suburban Woodcliff Lake, New Jersey. He’s just completed the second of three rounds of major dental work and has been injected with Novocain “everywhere,” he says. “The entire right side of my face is numb. I can’t feel anything.”

Antonoff’s eyes are pink and watery, and he keeps cocking his jaw and groaning, but that doesn’t stop the 30-year-old fun. guitarist from cheerily showing me the room he grew up in, ­every surface (including the ceiling) ­covered in posters and memorabilia—­Beatles dolls next to Anthrax stickers and Wayne’s World stills; windows covered in faded concert tickets for bands from Depeche Mode to the Max Weinberg 7; one wall just for Jimi Hendrix; another for skateboarding, ska, and Green Day (the band that got him started playing ­guitar); countless Broadway-cast albums and Playbills (Grease! Hairspray! Xanadu!); vinyl albums by the Stones and the Allman Brothers nailed to the wall; and a walk-in closet filled with the most impressive Star Wars memorabilia collection I’ve ever seen: figurines spilling out of three full bookcases and guarded by life-size cardboard cutouts of a Storm Trooper and Obi-Wan Kenobi. (Antonoff’s bar mitzvah was Star Wars–themed.) I nearly step on the envelope his good friend Taylor Swift gave him when she announced fun.’s Grammy nomination for 2012 Album of the Year. “I don’t know where to put this shit,” he says, pointing at a slew of gold and platinum records, mostly strewn on the floor. He thinks the “coolest” one is the platinum record for fun.’s 2012 Some Nights album. “Singles, whatever,” says Antonoff. “But selling a million albums feels like an impossible thing to do.”

He seems totally at home here, which isn’t surprising since he never technically moved out. He lived with his parents full-time (or as much as anyone who tours eight months a year lives anywhere) until only a year and a half ago—after fun.’s “set the world on fi-ire” rallying-cry single “We Are Young” went five times platinum and spent six weeks at the top of the Billboard Hot 100 chart, hit No. 1 everywhere from Australia to Mexico, won the Grammy for Song of the Year, got covered on Glee, and appeared in two Super Bowl commercials, for Chevy and Taco Bell. That’s when he got a place with his older sister, fashion designer Rachel Antonoff, on the Upper West Side and then, soon after, moved in with his girlfriend, Girls creator and star Lena Dunham, in Brooklyn Heights, both times leaving all his stuff behind in New Jersey. But this house is where he recorded the first fun. album, 2009’s Aim and Ignite; and where he dreamed up his deeply personal, ’80s-­nostalgia solo project, Bleachers, its first album out next month; and where he probably began plotting his one-man takeover of the pop-song ghostwriting industry—which happens to be going pretty well: He co-wrote Taylor Swift’s Golden Globe–nominated “Sweeter Than Fiction” and Sara Bareilles’s “Brave.”

“I never felt compelled to move out,” Antonoff says. “When the band wasn’t successful, all my neighbors thought, Oh, he’s probably in some shitty band, smoking pot. And then when things started going better, everyone was like, Oh, he must be mentally ill.

Coming home still seems like a pleasant regression for him. When he drives me to meet his mother, Shira, for a quick bite at a local bagel shop, Antonoff doesn’t even bring a wallet. “Don’t worry about it,” he says. “We can get my mom to pay.”

“He has this thing he does—‘I didn’t bring my wallet,’ ” says Rachel. “I think he just values things staying the same. He’s not cheap; he’s actually very generous. He’ll take you somewhere and fly you first class. But he’ll still never pay for the bagels.” Speaking of which, he insists on soldiering his way through an egg-and-cheese—with cries of “Ow!” about once a minute—against his dentist’s order that he stay off solid foods lest he bite his numb cheek and start bleeding.

“You have a little bit of lip droop,” his mother says soon after she walks in. “You know your nose is swollen out to here, right?” Then she apologizes; it’s probably her genes that made him so prone to cavities despite regular flossing and brushing. “I don’t eat Fun Dip at night or anything,” he says. He tells her he had “another close call with a root canal”; this visit, like the last one, ended with a horrifying, moment-of-truth drilling.

The real surprise, though, came when he went to check out. “They informed me that you’re no longer paying for it?” he says. “They were like, ‘All right, see you next time.’ I was like, ‘Send the bill to my house.’ And they were like, ‘We were told not to do that anymore.’ And I was like, ‘Really?’ ’’

“Um,” says his mother, “it’s something that Dad suggested, that perhaps you’re at a place in your life where you might want to pay for the dentist. We got the last bill. Your mouth is costing a ton of money. Are you supposed to be eating a bagel?”

“It’s wearing off,” says Antonoff. “Ow!” He’s so tired from holding his jaw open for hours, he says, that he can’t even get excited about fun.’s opening for Bruce Springsteen at a free concert in Dallas the following weekend, and he’s skipping a Miley Cyrus concert at the Meadowlands he really wanted to check out. “She’s a good performer,” says his mother. “I just … She takes it a little far for me.”

“You don’t need to have an opinion,” says Antonoff, kneading his face.

Shira playfully swats his hand away from his cheek—“Give it up,” she says—then walks over to the cashier. “This I can pay for,” she shouts back at him. “The ­dentist you can pay for!”

Photo: Christopher Anderson/Magnum Photos/New York Magazine Photo: Christopher Anderson/ Magnum Photos/New York Magazine

It turns out I’d seen Antonoff’s mother before, though we hadn’t been introduced. She’d been that lady enthusiastically cheering him on, alongside his father, Rick, in the row in front of me when Bleachers played their first single, “I Wanna Get Better,” during the fifth week of Late Night With Seth Meyers. “What was my mom like?” Antonoff wants to know when we first meet, immediately after that show. I tell him she asked Meyers a question about Bill Hader’s SNL character Stefon in an audience Q&A (“She did?!”) and seemed friendly. “Like really friendly,” he says, laughing. “Like talk-to-people-on-planes friendly. Which is like the final frontier of friendly.”

Antonoff is also a spill-your-guts-to-anyone-you-meet kind of guy. As soon as he sits down, I get a Cliffs Notes rundown of the tragedies that have shaped his life, the neuroses he carries with him from them, and the psychologists, anti-­anxiety meds, and other various coping mechanisms he uses to deal with them. The first thing he does when he walks onto any plane is sterilize the seat with anti-bacterial wipes, he says. “Everyone looks at me like I’m a fucking nut, but when was the last time you saw someone clean a plane? It’s just gross.” He always hugs hello and good-bye—that’s not just friendliness; he avoids shaking hands. He won’t sing into anyone else’s mike and doesn’t play brass instruments, because “talk about a cesspool for disease, a trumpet?” He’s an avid Uber user and jokes he hasn’t been on public transit since 2001, though that’s only partly because of germs; he also saw a dude pull his dick out on a train and it really freaked him out. It’s gotten worse since he caught “horrible pneumonia” three years ago after being “destroyed” by too many late nights in the studio finishing fun.’s Some Nights album. “I almost died,” he says. “I didn’t know you could get sick like that, short of, like, cancer or AIDS or having your leg chopped off.” He’d already been diagnosed with pneumonia when he got a 103-degree fever and went to a doctor “who I should’ve fucking sued,” who saw he was on anti-anxiety meds and told him he was just having a panic attack and he needed to go home and take a Valium. “And I was like, I’m not having a fucking panic attack. I know what that feels like. But I go home, I take a Valium, and then it feels like someone is stabbing me in my right lung.” He was having a septic reaction. His mother rushed him to the ER at two in the morning; his blood pressure dropped to 60 over 40. “It was like a movie. They threw me on a table, jamming things in me.” He stayed in the ICU overnight, was in the hospital for five days, was at home on an IV for a month, and “was out of my life for literally three months,” he says. He wound up with bronchiectasis, or scarring on his lung, which makes him prone to getting sick, which happened all the time when fun. was on tour last year and there was no time to get better. “You get to a point where everything is so important. One day you have Letterman and the next day you’re at the MTV Movie Awards and the next day you have a sold-out show for over 15,000 people. You can’t cancel anything, because it’s just too much to let everyone down, which is an interesting thing about being in a bigger band. It becomes such a monster in a good way, but you have a 30-person crew. They all have kids. You can’t just cancel a show.”

We’re the only customers in an exaggeratedly opulent, oak­-paneled, Victorian-themed midtown bar, Rarities, hidden behind a door on the mezzanine of the Palace Hotel. “These vibes! What is this place? Where are we?” asks Antonoff, somewhat delighted, though he really just wants some soup. There’s no food, alas, except for bar nuts. “God, as if I’m going to eat those. It’s like everybody’s hands—I just can’t imagine that they take the bowl off the counter, scrub it, and put fresh ones in. I feel like it’s this ongoing bowl of nuts.”

He asks for mint tea, but settles for sparkling water, which he orders from a red-haired waitress we nickname “Melisandre” after the character in Game of Thrones. He hasn’t given up drinking; he just doesn’t drink much: “I feel like reality is interesting enough.” Though “I was high from like 2000 to 2004,” I later hear him say, everything from pot to opium, until he stopped cold turkey after a really bad mushroom trip that messed him up for a week. He refers to it in “I Wanna Get Better,” a summer jam with a self-improvement chorus (“I wanna get better! Better! Better! Better!”) that he considers to be his “mission statement” because it “goes very specifically through every shitty thing that’s happened to me”: “I feel like I missed a whole period of my childhood because I had a bunch of stressful things happen to me when I was like 17, 18, when people usually feel the most free in life, like going to college and like anything is possible,” he says. “When I was 18, my sister died, and 9/11 happened. And then my cousin was killed in the war. It was like this whole balled-up moment, like before and after. Like, really, age of innocence over. All my friends were in college, they were super-loose, getting fucked up, in a very free place. And I was really weighted down by, like, life stuff.”

He still writes mostly about that time, especially for Bleachers, a sort of musical diary that is probably the rawest expression of self for a songwriter who’s flooded the pop-music landscape with raw expressions of self: The album, Strange Desire, is synth-heavy stadium rock like “Dancing in the Dark” crossed with Depeche Mode and the sonic weirdness of Yeezus. But there’s a certain amount of both humility and fear of failure in not launching his solo career under his own name. The name “Bleachers” is meant to evoke the “disconnected, darker side” of suburban youth, and Antonoff says he was inspired by John Hughes movies and how they were “tied to a time when big songs were great songs.” He’s been contemplating the project for a decade, slowly building samples he wanted to save for himself, like a looped bit of voice-mail from his sister or the recording of Dunham shouting the word “Go!” that appears on the bridge of “I Wanna Get Better.” He persuaded Grimes to loop some vocals, and got Yoko Ono to come to the studio: “She came in, she ate a bunch of Christmas cookies that were on the counter, which was weird for some reason, but I think Yoko Ono doing anything is fascinating,” says Antonoff. “She goes into the booth, and the first thing she does is scream at the top of her lungs and, like, blows the fucking compressors.” He wrote the songs alone on his laptop in hotel rooms from Malaysia to New Zealand on fun.’s world tour, then back home at his parents’, mostly in his younger sister Sarah’s frozen-in-time old room, which was strewn with recording equipment and guitars when I visited; Antonoff would often sleep on the floor.

Sarah lost her lifelong battle with brain cancer when she was 13 and Antonoff was a senior in high school, but his adolescence might have been marked even more profoundly by his family’s struggle than her dying, by those memories of hospitals and growing up in constant fear. “It’s not groundbreaking psychological stuff,” says Antonoff of his “germ issues.” “It’s coming from a very obvious place. You know, the scarring on the lung is not a big fucking deal. It’s just that in the context of my life, it just stresses me out. My real sickness is how I deal with it psychologically.” He’s seeing a psychopharmacologist and really needs to find a new therapist, but he gets stressed out thinking about starting over—not because he has a problem bringing up painful things but because of “the boredom of catching someone up.” He laughs. “Anyway, long answer to your question about why I drink tea. You realize that’s how this started, right?” We’ve been talking for only ten minutes.

Antonoff with Dunham, in an Instagram post from December: “The best day,” she wrote.

Antonoff doesn’t look much like the type of rock star who would incite teenage riots (though he almost did once, last year, when he accepted the key to his hometown at a senior center and fans swarmed). He wears black horn-rimmed glasses. His head is shaved but for a thick stripe of curls on the top. “I like to look like a big kid, and I feel like I can pull off, like, vaguely Nazi looks because my face is so Jewish,” he says of his style, which his sister says draws on the postapocalyptic comic-strip-inspired movie Tank Girl: a baseball cap perched high and askew, a sweater striped with every neon color, faded rock T-shirts with Army-green button-downs, his mother’s oversize wool coat from the 1970s, tight jeans, combat boots, an EMBRACE GRACE button from Dunham’s sister’s middle-school class-president campaign, and his favorite black-and-yellow-striped socks, pulled halfway up his calves. I see him wear the same sweater onstage two days in a row and the same striped socks—the same pair—for three.

But his music (both as fun.’s co-songwriter, alongside front man Nate Ruess and keyboardist Andrew Dost, and now with Bleachers) seems to tap into an epicness that’s been missing from pop radio of late: unironic, Queen-style, sing-along catharsis, with beats that feel like battle drums and choruses that demand to be screamed out a car window racing down a highway by angsty youth, many of whom, particularly from the LGBTQ community, gather outside his concerts 12 hours before curtain. It’s the kind of music that got him through his ’90s adolescence, which is when he started, playing firehouses, Legion halls, and Elks lodges with his first, straight-edge punk band, Outline, at 14. When he was 15, he and his best friend (who had his own band) set up their own tour though Texas, Florida, Tennessee, and North Carolina. It was early internet days, so they used a paper directory of club promoters called Book Your Own Fucking Life, got gigs everywhere from actual venues to anarchist bookstores, borrowed Antonoff’s parents’ minivan, and hit the road, unsupervised. The oldest guy in the band was 18, so he drove. “Half the time no one would show up or the equipment would be too fucked up to play,” says Antonoff, “but that’s when I fell in love with touring.” Written on the paint of his childhood room’s closet door is a meticulous log of every gig Outline played from 1998 to 2002, along with how much they got paid. Most of the time it’s “$0.”

That he got to go on that tour at all owes something to Sarah’s illness, which meant that, as children, Jack and Rachel had their freedom to a rather abnormal degree. One time in high school, for example, Rachel says, Jack borrowed the family minivan and called from the road to say he was on his way to Disney World. “I think my dad covered for him at school,” she says. His second, pop-punk band, Steel Train, got a record deal in Jack’s senior year, after Sarah’s death, and his parents gave him their blessing to skip college and hit the road. He basically didn’t stop touring for 11 years.

When Antonoff joined fun. in 2008, while still fronting Steel Train, the new band was kind of a second job. Along with Ruess and Dost, whose bands had just broken up, Antonoff had watched all his other friends drop out of music to get married or have kids or—horrors!—get jobs. “It was like Nate, Andrew, and I were always the ones still standing.” Antonoff, Rachel, Ruess (who was dating Rachel at the time), Dost, and another friend all moved into Jack’s parents’ house in New Jersey for a year and recorded much of fun.’s first album in the living room. “Jack used to call it Full House meets Grey Gardens,” says Rachel, who’s often sung backup on Jack’s songs. “We’d go to the mall and go to the Cheesecake Factory and Houston’s and then see a movie. We hung hard in New Jersey.”

In 2009, Antonoff went on tour with Steel Train, opening for Tegan and Sara, an indie-pop duo of twin lesbian sisters from Calgary who drew upwards of 2,000 people per show. By the summer of 2013, Steel Train had broken up and Tegan and Sara were opening for fun. to crowds of 15,000 to 20,000 people a night.

But instead of soaking that in, Antonoff has doubled down on work by branching away from fun., dipping into folders of music on his laptop filled with ideas that never made sense for his other bands. “I need a hobby, and I don’t want it to be ­basketball,” he says. “I want it to be music. So to get away from music, I do other music. If I’m producing someone’s song or writing with someone else, then doing a Bleachers song or a fun. song is an escape and it keeps me creative and it keeps me locked into what I want to do. If something’s making me crazy, I need to go somewhere else and I don’t want that thing to be yoga.” (He actually does run every day, but only because his pulmonologist told him to. “I hate it more than anything. It’s one of the most truly boring experiences on Earth.”)

One of those folders was what would become Bleachers. Another was beats and samples he wanted to use in pursuit of becoming the next in-demand songwriter for pop megastars—in the vein of Dr. Luke, Max Martin, or Benny Blanco. Both are moves that seem organic for a member of a Pro Tools generation less and less interested in snobbery and genre distinctions: starting a new band while already in one of the biggest bands in the world, and stepping out of the spotlight to ghostwrite ballads for other singers. Plus, his sister says, Antonoff’s major obsession growing up was listening to Z100, and he sees pop through brightly colored John Lennon sunglasses. Music “really does have the power to make the world a better place,” he says. “Like, we’re living in a better culture when we’re all walking around on the street and everybody’s listening to Nirvana and Pearl Jam than we are when everybody’s listening to Katy Perry or whatever.” (And don’t expect him to spend time with Justin Bieber. “You couldn’t pay me.”)

Breaking into co-writing, though, took immense hustle, since Antonoff had not proven that he could do it. So two years ago, he hired a manager, Tyler Childs, who started knocking on doors on his behalf. The first year was a lot of “outgoing calls,” Childs says. “I think early on it was a learning curve for people about who Jack Antonoff is. We encountered some people thinking he’s Nate or thinking he’s Andrew or like, Oh, let’s get all the fun. guys and write songs! I don’t think a lot of the A&R folks could differentiate them.”

Antonoff took what he could get, which included a “camp” for writing songs for Rihanna with other songwriters. “It was one of those experiences kind of when you walk into a party and you’re like, I know I’m not talking to anyone at this party. I’m gonna have some snacks and leave,” says Antonoff. “I really hated it, and I called up my manager after and I was like, ‘That’s not why I do this. I’m not here to get a hit song and get rich. I’m here to do things that make me want to enjoy my career and my life.’ ” He figured out he liked working directly with artists better, though even that can be a crapshoot. “Co-­writing is a weird thing because it’s either the most beautiful, amazing promise of what collaborative art should be, like two people creating something that is so much bigger than themselves—or it’s the most disgusting, awkward, shitty date you’ve ever been on. But it’s really worth it for when it’s great,” he says. And he kept an open mind: One of his first co-writing gigs was with Carly Rae Jepsen. “We got in the room, we talked about Robyn for a while, and we wrote this great song called ‘Sweetie,’ which I’m still really proud of,” he says. “I had, like, the best time.”

What “put him on the map,” according to Childs, was co-writing Bareilles’s “Brave,” which came out last year and is still playing in the background of Microsoft Windows commercials. They met through Sara Quin of Tegan and Sara, got breakfast, and decided to go into a studio. By the end of the second day, they were done. “It was like, That just happened, holy shit!” says Antonoff. “What I love about working with Jack is I feel like he’s got his arms stretched really wide,” says Bareilles. “He’ll take on big concepts and big sounds.” “What I love about Jack is that he’s not subtle,” Quin says.

Antonoff’s best letter of recommendation, though, is his ongoing collaboration with Taylor Swift. They met at the 2012 Europe Music Awards and became friends through the award-show-and-festival circuit. The “mainstream sector” of musicians isn’t very big, Antonoff says. “You start seeing people around. And, you know, it’s music. It’s not like everyone’s awesome. It’s not like a group of teachers. So it’s pretty easy to tell who’s garbage and who’s not right away, and most people suck, to be honest, or they’re just really wrapped up in what’s going on with themselves. And Taylor’s truly the nicest, most interesting person that I’ve met in that circle.” While hanging out at Swift’s house in Rhode Island, they bonded over their mutual love of a particular snare drum from a Fine Young Cannibals song. That became the inspiration for “Sweeter Than Fiction,” which they wrote by emailing ideas back and forth. “I think she’s a modern Joni Mitchell, I really do,” he says.

If Antonoff has a fourth job, it’s navigating the tricky waters of being in “a relationship that people are interested in,” as he puts it. He and Dunham met in April 2012, just after Girls had premiered and “We Are Young” was blowing up, when they were set up by Jack and Rachel’s good friend, the comedian Mike Birbiglia. “It was a blind date by modern standards,” says Antonoff. “I mean, I used the internet.” Dunham has said that she remembers Antonoff telling her that he thought all the articles about nudity on her show were “bullshit.” And that he still talks her through it whenever she gets upset about something she reads about herself.

That first date, Antonoff says, “I told Lena everything about my whole life, because when you really like someone, you want them to know everything about you.” That included his high-school sweetheart, Scarlett Johansson, who at the time they met in the Professional Children’s School was already acting in movies. “As abnormal as it sounds, it was as normal as anyone’s high-school relationship,” says Antonoff. (It might also be worth noting that he has said he was one of three straight people in his class.)

Both Antonoff and Dunham are productive creative people who’ve suffered from hypochondria and anxiety, and neither likes to party much. “We’re a good match in that department,” he says, telling the story of how they went to a spa retreat the weekend before his 30th birthday in April where they were the only people even remotely in their own age group. “Everyone else was 56 and, like, either coming off a divorce or trying to dry out. We were like, This is great! We love being here!” He has another one. “Here’s a perfect story for what we’re like: One time we were at a dinner party where everyone was over 60 and, before we knew it, we realized that everyone at the table had gone outside to smoke pot and they didn’t invite us. That basically says it all.”

In the two years since Antonoff and Dunham got together, both of them have gone from being relative unknowns to fairly famous. They just moved into a new apartment they bought together, and he’s become father to her rescue dog, Lamby, of whom they post so many photos on Instagram the pet gets recognized on the street with them. They are the most personable and accessible of all celebrity couples, opening a wide window onto their lives, filled with unflattering photos of each other sleeping or having just woken up—two very culturally relevant representatives of a generation that’s naturally inclined toward sharing, or oversharing. Still, Antonoff’s tolerance for exposing his relationship does seem to have limits: When I asked him about Dunham over brunch one day, he kept answering but stopped making eye contact and started very slowly mutilating a single raspberry in his yogurt.

Recently, they’ve had to deal with rumors that they’d broken up, after Star reported that they’d been witnessed having a screaming match outside Bowery Diner. Dunham defused the rumor with a two-part tweet, and Antonoff says he has no idea where that story comes from. “I feel like I always thought that everything I read was true, but my experience over the past year or so really blows my mind how not true certain things are. Like the flat-out lies I read in that story were like: ‘And Jack stormed back inside and paid the check.’ We didn’t eat there!” They’d actually gone to see Dunham’s mother’s art exhibit on the same street and then Antonoff had to go to the studio. “We got out of the car, went to the exhibit, went to the studio, and then the next day I got a call from my mom asking if I’d broken up with my girlfriend.”

In one video Antonoff posted on Instagram, Dunham waves her ring finger around and says, in an old-Jewish-lady voice, “I’m waiting! Hello!” Which of course made the news. Marriage is not happening anytime soon, Antonoff says, but they have talked about it. “I think all people in relationships that last longer than a year start talking about that stuff. It’s hard to imagine when the right time is because things are so crazy at the moment.” We’ve hit upon this subject matter as Antonoff is giving me a ride back to the city from New Jersey in Rachel’s beat-up Jetta, tracing the same highways he used to take to get to high school in Manhattan, past the spot on Route 4 where he totaled his car the third day of being a licensed driver and over the George Washington Bridge, where the first thing he thinks about, every time he crosses it, is how the towers fell just before his sister died, and “it just felt like everything was horribly evil,” he says.

And yet he’s “desperate” for kids. “It just seems like the most fun thing in the world. I’ve never met people who have kids who haven’t looked me in the eye and been like, ‘It’s the greatest thing that’s ever happened.’ ” He adds, “I think it’s biological. I’m 30. I’m not that young, right? I’m not, like, 24 or 22. I’m no longer in the phase of my life where I talk about everything as in the future. Like, I’m in the future.”

*This article appears in the June 16, 2014 issue of New York Magazine.

Jack Antonoff, a Pop Star a Mother Could Love