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Musician Jack Antonoff of Bleachers attends the 2014 Billboard Music Awards at the MGM Grand Garden Arena on May 18, 2014 in Las Vegas, Nevada. Musician Jack Antonoff of Bleachers attends the 2014 Billboard Music Awards at the MGM Grand Garden Arena on May 18, 2014 in Las Vegas, Nevada.

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23 Things You Learn About Jack Antonoff While Hanging Out With Him

Today, Jack Antonoff — through his solo project, Bleachers — releases Strange Desire, an event that has filled the fun. guitarist (and boyfriend to Lena Dunham) with total anxiety. "The past almost two years have been defined by making this album, so to transition from making the album to touring on the album and everything that comes afterwards, I didn't realize that (a) it's emotional; and (b) it's scary," he told New York's Jada Yuan when she spent a week with him this past spring. There were too many fun anecdotes from Antonoff and his friends and family to be contained in a magazine feature, which can only mean one thing: bonus Antonoff! Read on to hear about the cruel pranks he and his sister, fashion designer Rachel Antonoff, pull on each other; the real stories behind his and Dunham's Instagrams; and why he wants to be mainstream.

  1. You may want to take a Xanax if Jack Antonoff is driving you around. “Jack’s driving makes me very nervous all the time,” says his sister Rachel, adding that one of their best friends from growing up falls into a “fear sleep” every time Jack is at the wheel. I discover this feeling myself when he kindly offers to give me a lift back to Manhattan from New Jersey in his sister’s beat-up Volkswagen Jetta — with a warning that his license is expired and that I might do well to seek other forms of transportation. While weaving in and out of traffic, he constantly checks his phone and texts, yet makes incredible time. “How did you find my driving?” he asks me after pulling into a parking garage at, like, 20 mph. But he seems to know the answer already.
  2. This is a story he tells passengers as he drives them home: “I had a terrible accident right up here on the other side of the highway. I fell asleep. Third day I had my license, driving home from high school. And I completely totaled the car. And the car was in the middle of the road and all the cars were stopped on the highway and I got out and it was so terrifying because I was standing in this highway that I had driven down my whole life and everyone was staring at me like I should be dead. This door was here, the back was there. They had to basically throw the car out.”
  3. Despite his driving issues, Antonoff claims not to have ridden the subway since 2001 because of germs. But while in high school at the Professional Children’s School, he used to busk in the Columbus Circle Station. How much money did he make? “Tons! Like 40 or 50 bucks a day, which was, like, a lot of money, if you factor in inflation and that I also had an allowance.”
  4. Because he only travels by car, he almost never has a coat, even in the dead of winter, because he’s basically always going door-to-door. Strangely, he also told me he gets super “bitchy” whenever it’s cold. None of this makes sense.  
  5. He and Lena Dunham bonded about rising to fame simultaneously; they met just as fun. was getting big and Girls had just debuted on HBO. “We’ve had a lot of similar experiences that have been … comforting. To go through together,” he says. Now, their biggest problem is “the boring stuff, like scheduling,” he says. “Who gives a shit what anyone says or what happens? The only thing that’s hard in life is scheduling. You know, I have to tour so much and, like, I miss the people at home. And I miss things that happen. I miss birthdays. You miss stuff because scheduling is hard. I think the biggest problem in life is time. It’s not anything else. At the end of the day, I don’t sit around with anyone I love and talk about anything but scheduling.”
  6. When Jezebel started that weird non-controversy about Dunham’s Vogue cover by asking for un-retouched photos, Antonoff was supportive, but they didn’t make it a big deal at home. “Some things are so stupid it’s not worth even talking about,” he says. “I don’t need to say much because everyone has already said it. It’s not like we live in a horribly unfair world where when disgusting pieces of press come out the whole world doesn’t recognize it. I never feel upset about stuff when it’s obvious what it is. You know, like the verdict is in on Chris Brown. You know, we can sit here for ten years and talk about what a shitbag he is, but, like, everyone knows. When press says really gross stuff that is offensive and really, you know, just, like, off-topic, irrelevant, shitty, and mean. Just that’s it. It just, I don’t think about it too much.”
  7. It took a full year to close on his new apartment in Brooklyn Heights with Lena Dunham. “If you’d told me that when we bought it, I would have just exploded, like my head would have fallen off,” he says. They’d been looking to upgrade for a while since Dunham’s apartment felt too small for two people with a lot of stuff, plus a dog. Also, their neighbors were smokers, so their apartment always smelled. And, most irksome to Antonoff, the building was so old they only had two-pronged outlets, which meant they couldn’t plug in electronics that had three prongs, which is basically all modern electronics. The new place will have a studio for Antonoff and an office for Dunham, and hopefully a Victorian doghouse for their rescue dog, Lamby.
  8. For the record, Dunham didn’t learn that Antonoff had dated Scarlett Johansson by stumbling across photos of them in high school on the Tumblr Old Loves, as many tabloids interpreted a story she told Grantland’s Bill Simmons. “That whole thing got ridiculously blown up,” says Antonoff. The story was about Dunham’s surprise in seeing her boyfriend and his old relationship on a Tumblr she likes to checks obsessively. It wasn’t like she didn’t already know. “Yeah, what kind of sociopath …?” says Antonoff. “That’s what you do the first week of your relationship. Actually, on my first date with Lena, I told her everything about my whole life. Because when you really like someone, you want them to know everything about you.”
  9. Despite E! and Good Morning America reporting it as actual news, the Instagram photo of them hanging with the Obamas, bearing the caption “really sick double date,” was a joke. fun. had played on the White House lawn and the photo the couple snapped was clearly a fan pic. “It just kind of grossed me out,” says Antonoff. “It made me want to take a shower. Oh my God! — the idea that millions of people thought that I was the kind of person that would go on a double date with the Obamas and then post a picture ...” He did, however, get to take a tour of the Oval Office. The best part was catching a glimpse of Barack Obama’s phone, “and the speed dial was like, ‘Joe Biden’!”
  10. He loves a good prank. Rachel says he discovered this trick where you can remove yourself as a contact from anyone’s phone and then text them pretending to be someone else (since we live in an age where no one knows anyone’s phone number anymore). Once, when Rachel was a freelance music writer, she interviewed a cute singer from a band. Jack put his number in her phone under the guy’s name and sent her a text that said, “What’s up? I’m in town.” They started chatting back and forth, says Rachel, “And I was like in bed watching something embarrassing on TV like Frasier, and Jack as the guy was like, ‘What are you up to? I’m out.’ And I didn’t want to say, ‘Oh, I’m in bed, I’ll come meet you.”’ Because that would be pathetic. So I was like, ‘I’m out too, maybe I’ll stop by! Where are you?’ And he said, ‘I’m at the Cubby Hole,’ which is the bar next door to our apartment and I was like, Oh my God, It’s fate! Get up! So I got myself out of bed, put on clothes, I did my hair, and then Jack called and I was like, ‘You’ll never guess who I’m meeting!’ And he felt bad. He was like, ‘Oh, I didn’t think it would go this far.’” She also lost that guy’s number because Jack took it out of her phone. And she got dressed up and didn’t even get to hang with her brother, who was in New Jersey on tour. 
  11. For revenge, Rachel put up a whole bunch of ads on Craigslist listing his phone number. “At first they were very obvious, kind of dumb, you know, sexual stuff,” she says. Then she branched out. “I put up an ad that he was selling a whole bunch of Wizard of Oz figurines, and like went into detail about Dorothy’s chipped nose and all this stuff. And he was inundated from people wanting threesomes and wanting to buy his shiny red bike and just everything. It was great.”
  12. Antonoff still remembers the first time he flew first class, because it was just a couple years ago. fun. was blowing up, and for some random reason, their label upgraded Antonoff, frontman Nate Ruess, and keyboardist Andrew Dost for a flight from Australia to Japan. “I remember it was like next-level crazy for us,” says Antonoff. “Because it was international and they had sleepers and we’re with all these Australian and Japanese businessmen getting into their, like, Qantas pajamas, and the three of us were shouting at each other ‘New money!’ as a joke.”
  13. He’s really polite to waiters because they stress him out. “Someone could throw up on my fucking salad and I wouldn’t send it back. I would be like, ‘No, this is interesting,’” he says. “A waiter could treat me like a piece of shit and I wouldn’t say anything. I just don’t wanna fuck with them. There’s a lot of power there, they’re handling your food. I just feel very weird and shy. One time I was in a room with other people getting massages and some guy was like, saying things he did and didn’t want, and it just blew my mind. I just feel like the service industry, I don’t wanna fuck with anything.”
  14. Over brunch one day, he pulled out a tissue filled with ten vitamin supplements and took it in front of me. Among them: fish oil; the immune-booster immunokinoko; selenium; vitamin D “because I’m deficient”; a daily immune-booster called Cold FX; a probiotic; and an herb called astragulus. Psychopharmaceuticals, he says with a laugh, are “at the beginning of the day.”
  15. Antonoff has a huge LGBTQ following. He and Rachel founded an organization called the Ally Coalition that encourages straight artists to speak out about gay rights as human rights, and fun. donated a portion of their tour proceeds toward a shelter for homeless teens in Detroit. Also, “Brave” the song he co-wrote with Sara Bareilles, has become a gay anthem, which was part of their intent. They were having an impassioned discussion about it in the studio and the song became a  “love letter” to a friend of Barielles’s who was coming out at the time. “I felt with Jack kind of as the co-pilot it encompassed a more anthemic role,” she says. “I feel like he’s got his arms stretched out really wide, and I’m like nervous to stretch my arms out that wide. He just made it feel safe to embrace something bigger.”
  16. His latest co-writing ventures have been a song with Charli XCX (“a great writer”), a trip to Nashville to work with country artists, and something with Brooke Candy, the female rapper off Grimes's "Genesis" video. “She’s really fascinating,” Antonoff says. “She makes Gaga look like a nun.”
  17. He never went to college, but he did try to get in. But his grades were terrible and no music school would accept him. “I remember having lots of meetings with people who would basically kind of go on about how my songs were shitty. You know, like, guys in ponytails at some SUNY somewhere.” He told me that all his ideas of college come from movies and “the porn I watch.” 
  18. He personally hustled to get his idol, Vince Clarke of Depeche Mode and Erasure, to produce some tracks on the Bleachers album by asking him out to drink. “I think modern pop should just write Vince Clarke a check for a billion dollars,” says Antonoff, “because you listen to a modern pop album and it just sounds like bad Depeche Mode or bad Erasure with all the synths and drums.” But that didn’t stop Antonoff from trying to emulate Clarke’s sound. At their meeting, he says, “I told him about [Bleachers] and basically told him all the ways in which I was ripping him off and said I’d rather he do it than me try to do it,” says Antonoff. Clarke says he agreed because, “He seemed like a nice bloke.” And because he thought he had some “bits and pieces” to add to “I Wanna Get Better” and other tracks. “It’s great song, and it has a really good melody and a good message,” says Clarke. “ I thought it was very clever how he managed to get that much in in a short amount of time. Everything in that song contributes. There’s no spare parts.”
  19. He also talked Yoko Ono into being on the album. “I love Yoko — not the spectacle — the artist,” he says, “Like, I love what she does, I love how she represents these lines of Is it art because it’s Yoko or is it art because it’s brilliant?” So when he had the idea for a “Yoko-type part” on a song, he just thought he might as well ask. She came in the studio, he says, “And it’s just like she was everything you thought she’d be. She would do things that were bizarre and then she would do things that were brilliant, and then she would do things that you didn’t understand if they were bizarre or brilliant. I love artists that are making you look really deep, you know, and make you wonder. Not very few people have that power.”
  20. He also idolizes Bruce Springsteen and Tom Waits, but has very little interest in meeting them because it would burst the image he has in his head of them. “I heard a story about [Tom Waits] hanging out at a Blockbuster and talking to someone and it really pissed me off, imagining Waits at a Blockbuster. What the fuck was he doing at a Blockbuster?”
  21. It drives him crazy when people call Bleachers a side project. “One thing I’ve noticed about this project is people’s intense need to categorize,” he says. “It’s so stupid, and it’s such an annoying [thing] to simplify something that maybe isn’t simple. It’s just — I do this, I do that. People are always desperately searching for meanings of what’s going on. Is fun. breaking up? Did you miss not being a frontman? It’s just like, it’s all good. I wouldn’t be in that band if I didn’t like doing it, and I wouldn’t do this if I didn’t love doing it. I hope that people can hear by the music that it’s not reactionary. Bleachers isn’t apologizing for being in a band that won Grammys. It’s not like me making weird noises on like some old synths. It’s just as over the top as anything I’ve done. It’s not apologetic, it’s not reactionary; it’s a different project.”
  22. “I want to contribute to mainstream,” he says. “I don’t want to be reactionary and apologetic, and I don’t want to be in an indie band that, like, pulls back because it’s afraid of mainstream. I wanna go straightforward, but I wanna be better. And I think that’s something that got missing, where the '90s were great with Smashing Pumpkins and Nirvana, and then rap-metal happened and everyone was so embarrassed that it was like either you were indie, or you were pop, or you were hip-hop. And the indie I grew up with was very, I don’t even know how I got here, I’m just in a garage playing guitar, fuck it, I hate that shit. It’s so annoying. It takes so much to be in a band that to not fucking get up there and just kill almost ruins the spirit. Like, what fucking right do I have to ask people to pay money to see my show? Not just pay money, but get on the fucking subway, get in the fucking car, like, ruin a whole night of their lives just to see my show. Ask them to pay money to buy my album, T-shirts with my stupid face on it. What right do I have to do all of that, and then not say it’s good enough? More than good enough — to not say it’s special?
  23. He goes on: “I’m more in love and attached to the connection from music than I am to music. What I love doing is like working on things and imagining like the whole world hearing it. I’d rather have an impact on a bigger level, and I’d rather believe in what I do and think it’s worth having a cultural impact and then going for that instead of existing in some subculture. I think it’s bullshit and it’s tiring. You know what’s cool? To be awesome and mainstream, not to be awesome and only let a certain amount of people hear it. And I just feel very attached to that and try to be less ashamed of feeling that way. Because it kind of feels like you have to be either hunched over your guitar not giving a shit, or Kanye, and there has to be a middle ground.”

* This post has been updated to correct two typos. (Sorry, Brooke Candy and Vince Clarke.)

Photo: Frazer Harrison/Getty Images