Jack Antonoff on the Hardest and Most Surprising Music of His Career

A Vulture series in which artists judge the best and worst of their own careers.

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Even though they’ve recorded three albums together, Jack Antonoff doesn’t ever remember officially booking a studio session with Lana Del Rey. “We’ll just text and be like, ‘Where are you?’ ‘Okay, come over,’” he says. “I was with her the other day and we just went to the studio and started messing around. It’s very loose.” That casualness sets the tone for the whole recording process, no matter what kind of song they’re working on. “The music can be so incredibly serious, and we just end up trolling each other and being funny the whole time.”

Antonoff is feeling reflective as he whirls around his New York apartment, making coffee and getting ready to go out with his sister, Rachel Antonoff, and wife, Margaret Qualley. When he thinks back on the past year and change, he’s grateful to have close collaborators like Del Rey, along with his friend Taylor Swift and his band Bleachers. Those bonds paid off when Antonoff was nominated for six Grammys earlier this year — including what could be his third Producer of the Year in a row — largely thanks to his production work on Swift’s Midnights and Del Rey’s Did You Know That There’s a Tunnel Under Ocean Blvd. “A lot of creative industries, especially nowadays, are so obsessed with these harsh pivots, so it’s not common to have really long-term collaborators,” he says over video call. He’s also produced multiple albums for Lorde and St. Vincent and recently added the 1975 to his cadre. While some fans accuse him of adding too much of his ’80s pop style or dulling their favorite musicians’ best qualities, the artists themselves keep coming back — none more than Swift, whom he’s worked with since her 2014 album, 1989. “We will continue working together till 2089,” she said, joking, as she accepted an award at this year’s VMAs.

Safe to say Antonoff feels the same way about Bleachers, the group he started in 2014 as his own E Street Band. He’d spent the bulk of his performing career jumping between bands, from his grade-school punk band Outline to the jaunty rock outfit Steel Train to the indie-pop supergroup fun. Now, as he’s preparing to release Bleachers’ self-titled fourth album next March, he’s writing in new styles and breaking down the barriers between the band and his solo production. But throughout our conversation, he can’t stop coming back to Del Rey’s “A&W,” which was nominated for Song of the Year this year. “We didn’t say this in the room, but it’s the kind of song where you would be like, Well, it’s definitely not getting nominated for a Grammy!” he says of the seven-minute, two-part opus. “But, you know what, Lana and Taylor and this year I’ve had, I think the through-line is keep finding things that fucking thrill you. To do anything but push and find new ground is a bastardization of the job.”

Maybe “Mastermind.” We made the bulk of that album in my apartment. There’s a little studio in there, which is the same place that we’ve worked for many years. It feels like we have such a bedrock beneath us of things that we know that we can do that it makes it really feel possible to stretch. And I remember when we were making “Mastermind,” we were laughing at each other about going this way and that way. It’s a strange little song, and it just reminded me of the kind of thing that you can do with really close friends, whereas if it was a new relationship, you might not be able to dare to suck. Like, just try some weird shit. Because every once in a while, when you really throw yourself out there, you actually get the stuff that’s the most brilliant.

Oh, every one. I’ve never been in a room with her and felt like we were doing anything but treading new ground that we’ve let last for even ten seconds. If we’re not feeling it, we’ll move right the hell along. What I think is fascinating about songwriting is you can’t fake it. There’s no shortcut; it comes or it doesn’t. But the one thing that the years can do for you is at least recognize when it’s not happening and get off quicker. When I was 19, I might go down a rabbit hole of some weird shit because I would care about the amount of time or the resources I put into it, and the more I do it, the more I realize that that’s a fool’s errand. You show up, you hope to grab it, and you do or you don’t. When I’m with my collaborators, the further we go down the road, the more we’re only vibrating on the really special stuff.

We’ve been at this point for many years. I mean, we started working together on ’89, we did a ton of work on Reputation, which was so wonderful and intense, and then Lover, we started to do some more strange things. When we did Folklore, that was obviously a really different angle, and some of the earlier songs, like “August” and “Mirrorball,” are some of my favorite things we’ve ever done. You know, writing a song and collaborating with somebody, once you do it, you’re like, Well, who knows if that’ll ever happen again, ’cause it’s just magic. With her, I’m constantly taken aback. I’ll joke with her sometimes when we get something crazy, like, “Okay, I guess we still fucking got it!” There’s really nothing for her and I left to do if we’re not completely stretching ourselves out there into the darkness. And that was the whole story with Midnights — we did so many things that we had never done before.

I don’t work with any soft synths, so everything is a sound that’s made in the room. The funny thing is you can’t recall the sounds. So all the Bleachers guys helped a ton on that stuff. It became a really fun project for me and the band. It was like, “All right, Mikey, here are the Juno tracks, do your best.” “Sean, here’s the drum stuff, see what you can do.” And then I’ll have X amount of tracks that are just sound from the room. The internet was really interested in what sounded like a seagull sound in “Is It Over Now?” It was really fun, because it was all these analog instruments that we know and love: Moog model Ds, Juno-6s.

I would liken it to finding an old diary. There are so many things on so many of those sessions that I was like, Oh, you little freak. Little layering I would do then, ’cause you go through phases, and it made me feel really sweet. That younger version of me that was just piling shit on, I mean, “Out of the Woods” is just like kitchen sink. That’s the glory of it: As someone who didn’t really have any success as a producer, there was no reason for me to pile all that shit on other than it was just giving me a lot of joy. And it made this weird, messy symphony and I love it to this day.

Definitely “Peppers.” Or “Taco Truck.” But Lana’s from Lake Placid and I’m from New Jersey. She’s lived in California for a long time, so she really lives the life, but I do feel like both of us have this dream of California from growing up on the East Coast. Very often, someone’s idea of what a thing is can be a funnier, weirder version of what the thing is.

I actually think the most California song we’ve ever made is “Venice Bitch,” and not for the obvious Venice line. I was thinking a lot about the space between Dick Dale and John Frusciante on the guitars; the drums, when I was playing them, I wanted them to feel like the early 2000s shoegaze scene that was happening out there. So I’m not saying it’s a California thing — it’s a New Jersey person’s impression of California.

She and I will write a lot, and then the framework of the albums will come together. For example, “Jimmy,” which ended up on “A&W,” was written during the Norman Fucking Rockwell sessions. So, the “Venice Bitch” at the end of “Taco Truck” is the original version of “Venice Bitch.” When we were doing Norman Rockwell, we had this whole idea of being up in Laurel Canyon and driving the truck down to the club. We moved on from that concept, so I had this original “Venice Bitch.” After we did “A&W,” where you have a song like “Jimmy” from that time period melding into it, I thought, This whole album is so sprawling and freaky. I just started putting things in weird places. This is another example of like, when you work with someone for a long time, you can start really getting weird. That was the theme of that album: Let’s get fucking weird.

I’m not easily shocked, but the stuff that shocks or surprises me is often the most beautifully written stuff. A lot of his funnier, snarkier stuff that’s maybe more designed to shock, that’s one corner, but the stuff that really knocks me off my feet is when someone says something that just feels like a gut punch. The first song, Matty had that line, “I’m sorry if you’re living and you’re 17,” which cuts me so much that I pushed it to become a repetitive thing. It’s not even about speaking to people that age — “I’m sorry if you’re living and you’re 17” just feels so much like the experience of this moment. The one thing everyone agrees on is this grand failure of generations to come. When we were making that album, it was a pretty polarizing time in general, and that line just felt like a relief of a fact.

But yeah, the stuff that shocks me the most is someone’s vulnerability in a song. The end of “You’re on Your Own, Kid” is one of those moments for me. I remember, she wrote that right in front of me and then we put it down, and I was completely punched in the gut. Beautiful.

There’s a song called “Tiny Moves,” which no one’s heard yet. The real story there is I started writing music when I was 14 or 15, and my younger sister was sick then. She died when I was 18, so all my formative experiences with writing music were writing about this massive, heavy, big loss and grief. Then, obviously, that grief grows and changes. It’s such a fertile place to write from, and I’d felt a little bit resigned, not in a comfortable way, just like, Okay, my place in life as a writer is to write about loss through the lens of age. And don’t get me wrong, there’s tons of that on this album. But I met my now-wife, and it feels like a lot of the mythology and armor that I wore — we all say, like, “I can’t get relationships right,” “I don’t do this,” “I’m bad at this.” And when you have a big shift like that, which was really meeting my person, it’s brilliant and amazing, but it’s also destabilizing ’cause you have to deal with all of the past, where you lived by this code that was bullshit. And within that, I found myself writing more conversationally, very deep and very intense. How do you have such a great loss and then also explore other parts of life? I wasn’t able to do that in the past, because I felt like it was not honoring my loss to write about anything else. So, this is the first album where I explore other things, and there’s presence to it that I haven’t had.

​​Either “Everybody Lost Somebody” or “Modern Girl.” Both those parts were written by Evan Smith, who’s one of our saxophone players. “Modern Girl” felt like a big, Knock down the front door, we’re back! It’s giving me something that I felt like has been missing for a long time, which is, there’s so much weight in my music and there’s so much intensity, and there’s so much fucking weight in the world, and I just wanted music to be fucking fun and irreverent again. I wrote this whole song that basically roasts culture, roasts myself, has every inside joke about the band. It’s kind of a love letter to the fans, it’s kind of a fuck-you to the things that bother me out there in the world, and most importantly, we’re having a fucking blast playing it. Then also, you just don’t hear saxophone out there, so I thought, Let’s have the first thing people hear from the next album be this sax played like its head is on fire, and anyone who’s not feeling it is not who we’re looking for.

One thing I’m not sure that everyone fully understands: fun. was sort of this, like, left pivot. I’ve always written my own lyrics to my own songs, so it really went Outline, Steel Train, Bleachers, with production peppered through all of that. You know, fun. was this side project I started, with three friends, but it just had this funny hit, so it felt so front and center. But the ladder is Steel Train into Bleachers. I mean, the time between writing “Bullet” and “Rollercoaster” wasn’t very far off.

There’s a song called “S.O.G Burning in Hell,” which I feel like has a Bleachers-ness to it. It feels like trying to break through to that controlled chaos thing. That’s a huge thing that I’m always after, that feeling of like, Is this thing gonna stay on the track? Like, I always want the audience to feel both safe and terrified all at once. I think with Bleachers, it really crystallized.

It’s pretty rare that something is impossible to write or arrange. It’s more like, I can get very obsessive on making the sound be what I hear in my head. I feel like the process is like either you capture this crazy lightning in a bottle and then you spend your time protecting it, or you have this crazy idea of what you want something to be. Did you ever hear that Lorde song “Hard Feelings”? The end of that, production-wise, I was so obsessed with wanting it to be these crazy Transformers fighting sounds, but also really warm. I went really crazy on that. Melodrama was a really intense process. We were just tearing stuff apart. We’d do one thing one day, zero it out, try a whole other thing.

The end of “August,” the strings and twangy guitar — that was one where it was really in my head, production-wise, for a long time. The end has to be so euphoric. She’s talking about, like, “Meet me behind the mall” and “Back when we were living for the hope of it all.” I kept attaching to all of her lyrics and being like, This crescendo at the end has to feel like all of that, on fire.

The second Bleachers album, Gone Now, almost killed me, because I felt so fucking obsessive about what I had to say after being given the success I had off the first album. Like, This is the moment, I have to get this right. That second-album anxiety is pretty fucking heavy and with good reason. You’re given an opportunity, and you’re just standing there remembering all the things that you thought your whole life that you had that opportunity.

You know, there’s not really one. Like, stuff on Bleachers albums, it’s so separate. I’ve written songs with Lana that have been on Bleachers albums, obviously “Alma Mater.” When I was exiting fun. and trying to get everyone to focus on Bleachers, but also wanting people to understand what I did as a producer, I feel like I created a lot of separation. Like, This is when I’m in the studio for Bleachers. This is when I’m in the studio producing an album. But it wasn’t very true, to be honest. It’s a pretty connected group of friends and we’re bouncing around a lot, playing on each other’s records, writing records with each other. I don’t regret creating that narrative, but it’s not the most truthful one. I care less about that now, because I feel like I can recognize a community around it.

This interview has been edited for clarity.

Swift, for her part, recently said the song was inspired by the end of Phantom Thread: “I thought, wouldn’t it be fun to have a lyric about being calculated?” Specifically “Out of the Woods,” “I Wish You Would,” and “You Are in Love,” the three tracks Antonoff originally produced on 1989. Mikey Freedom Hart, who plays keys and guitars in Bleachers. Sean Hutchinson, who drums in Bleachers. Like this verse from “Part of the Band”: “I know some vaccinista tote-bag-chic baristas / Sittin’ in east on their communista keisters / Writing about their ejaculations.” In the bridge, Swift reflects on the arc of her music career: “‘Cause there were pages turned with the bridges burned / Everything you lose is a step you take.” Sarah Antonoff had brain cancer. “I guess I’m New Jersey’s finest New Yorker / Unreliable reporter / Pop music hoarder / Some guy playin’ quarters.” “We Are Young,” the unlikely No. 1 that earned Antonoff one of his first Grammys, for Song of the Year.