We’ve Got A File On You features interviews in which artists share the stories behind the extracurricular activities that dot their careers: acting gigs, guest appearances, random internet ephemera, etc.

As Future Islands frontman Samuel T. Herring once sang, seasons change. “Seasons (Waiting On You)” — and the band’s viral performance of the song on Letterman, highlighted by Herring’s growling, crooning vocal and intensely physical dance moves — remains a watershed moment in their career. But we’re now a decade beyond all that, and Herring’s past few years have provided no shortage of discussion fodder.

After experiencing the dissolution of a long-term, long-distance relationship and an international move, he has made his acting debut as a major character in Apple TV+’s horror series The Changeling, guested on a billy woods and Kenny Segal album, and toured with Weezer and Joyce Manor. “I live a varied life,” the singer and rapper quips. Somehow, he found the time to make a wonderful new record with Future Islands, too. Out this week, People Who Aren’t There Anymore contains some of their sharpest songwriting to date, from the fist-pumping, anthemic “The Tower” to the poignant, ruminative “Give Me The Ghost Back.”

A renaissance man like Herring makes a wonderful subject for a career-spanning interview. He graciously gave two hours of his time to discuss his old performance-art band Art Lord & The Self-Portraits, linking up with Madlib and Kenny Segal, doing rap battles in his school cafeteria, that legendary Letterman performance, and much more.

People Who Aren’t There Anymore (2024)

How do you think this album paves a new path forward for you guys?

SAMUEL T. HERRING: For years, we’ve been trying to figure out how to capture ourselves and what we believe is our best form. You can really hear the difference in the way our first, second, and third albums sounded compared to our fourth album, which was our first time in the studio, and then how things have grown from there.

Within the canon of Future Islands, I think this is our best-sounding record, as far as capturing the emotions the way we want to portray them and the live performance. We’ve always felt comfortable as a live band. That’s where we feel our music connects the most; that’s where we feel like the songs are always the freshest when they’re done. We’ve probably played “Tin Man” 1,000 times, and it gets better. That’s a good thing, like the things that are learned through those performances. That’s always the tricky thing about creating an album is, with this record in particular, there are probably eight songs that we haven’t played live. In two years, the songs are probably gonna be better than they are on the record! [laughs]

That’s an unfortunate part of the way the process of albums can be sometimes. But I’m really proud of this. With the last record, As Long As You Are, that was the first time we made a record where me, William [Cashion], and Gerrit [Welmers] didn’t have any regrets about how it sounded. With every previous record, at least one of us had an issue, whether the vocals didn’t sound right, or they were too varied, or they were too loud, or the bass was too quiet, or the bass was too loud, or the keys were treated wrong. Because of the pandemic, we had the time to be like, “Let’s make sure everybody’s happy for the first time.” That was the record I felt was us at our best. So it’s nice to go from there and then build upon that.

We took our time with [People Who Aren’t There Anymore] to let it grow. Some of the songs grew and, over time, changed meanings, even within the time of the writing and recording of the album. Some of the songs are still revealing themselves because the back half of the record was written after a devastating period for me. If you listen to other Future Islands songs, it’s me singing about a long past, or maybe a not-so-close past, but it’s like a reflection. These were songs written in really emotional times, so there’s still some reckoning and understanding to be gained. So I’m curious how the songs will grow and how the next group of songs speaks to this.

What are some of the songs that have changed meaning since you initially wrote them?

HERRING: “Say Goodbye” was written around July 2021. My ex is Swedish, so I was spending most of my time there up until the pandemic, and then I went home right at the beginning of the pandemic to finish mixing the last record. A couple days after I got back, the whole country’s borders shut down. And then Europe was shutting down. There was this seven-month period where we did not see each other. That was through 2020, and I finally got back over there at the end of 2020, but then I had to leave again because you can spend only three months there. So then I have to leave for three months, and then I went back for three months, and there’s this back and forth. But in July of that year, I was writing “Say Goodbye.” It’s really about these time zones, where I’m waking up and reaching out to someone who is saying good night, and then I go through my day. Then they wake up and say good morning, and I say good night. They were these feelings of not really knowing if we were going to see each other again and trying to comfort each other in a time where the whole world was changing. But the song was written in the sense of like, “This is really hard, but we’re still there for each other. And we’re going to get to the other side of this.”

“Deep In The Night” is another example of a song that was written with that in mind, like, “We still have this love; it’s going to carry us to the end, and I will find you.” But at the end of 2021, we split up. The pandemic is basically [air quotes] over, and then I finally got residency in Sweden and we bought an apartment. But the disassociation that we both had to go through, to get through that time apart, meant the connection was gone. You have to turn off your emotions so that you’re not broken. Then you have to turn them on again when you’re together. Then you have to turn them off again when you’re apart. Sometimes you go to turn them on again, and they aren’t there anymore.

Going back and looking at the songs that were five months or a year old were like, “I’m here waiting, and we’re going to be together.” These weren’t songs about a love that was holding on. This was a love that was going away. The songs are actually chronicling the growing difficulty of waiting – the growing difficulty of holding on. These songs aren’t about someone who is there waiting for me. They’re songs about someone who is slipping away. So it’s strange; the words didn’t change, but the feeling changed and the understanding of it changed, and that was brutal. It was brutal to be like, “Oh, I thought I was writing a love song. But this wasn’t what I thought it was.” That’s something I’m still learning about.

There’s also a difference between “The Sickness” and “Corner Of My Eye” because “The Sickness” is blaming the whole world for what happens. “Corner Of My Eye” says, “This is just how it happened. We had this life; we had a home; we were best friends. And now it’s gone. And I have to accept that and be gracious for the time that I had.” The last line is probably one of the most perfectly brutal lines I’ve ever written that I’m really proud of, which is “It’s perfect/ So it’s done.” Myself being a perfectionist, I understand what that means, holding on to that ideal vision. But the truth is, “It was perfect. So it’s done. There’s nothing more to do.” If you talk about older Future Islands songs, they change because sometimes we find ourselves going through a similar thing we’ve already been through in our lives, and that’s a really devastating thing. Like, “Wow, I wrote a song 10 years ago that is about the exact thing I’m going through right now. I need to start working on myself a little bit and figure out why I’m repeating these cycles that are leading me down these paths.”

Does the title of the album reflect what you were talking about earlier: someone who’s a constant presence in your life and suddenly not speaking to them anymore?

HERRING: This title really spoke to all of us in different ways. It could be the title for a lot of Future Islands albums. It’s something that we speak about in our music: looking for knowledge to gain from the past. That’s the acceptance that I have found through the last six or seven years. Of course, I’m not all the way there. Life is long. “The Garden Wheel,” for instance, really speaks to putting life in that idea of nature: the way nature takes from nature and love takes from love. These things happen to us, and not everything is against us. Sometimes, the world does take over your whole life, and people slip away. How many of us have a person that we spoke to every day when we were kids or in high school that we don’t know where they are or what they’re doing? The person I was 20 years ago is not here anymore, and that’s OK. I accept who I was then and what I went through. Sometimes, I wish there were parts of that person that did still exist, but we change. We are the people who aren’t there anymore. There are the other people who are missing, but we’re also the missing people.

Also, this is your first time working with Chris Coady since Singles. What was it like getting back together with Chris?

HERRING: It was cool. The album was co-mixed between Steve Wright, who was the producer, co-producer, and mixer of our last album, and then he was co-producing this record. We basically got to the very end of the mixing process, and we started to talk about if there was anything we were missing. So it was initially just an idea that William really wanted to pursue, which was like, “Could Chris add something to this?” Through the process of trying to take some of these mixes back to zero, we had gotten them very far and found a lot of clarity and dynamics within the flows. Chris coming in very fresh, he added something, but we also felt like we were missing the dynamic.

We ended up doing a hybrid thing where we had Chris mix from Steve’s mixes to preserve the dynamics. But there was something about Chris’ mixes that had some vibe to the sounds that he was creating. So we’re like, in a perfect world, we could hybridize that. It was really amazing because this doesn’t happen, like people don’t do this. A mixer is like, “No, I’m not going to mix somebody else’s work. I want to do my own work.” So they were really gracious to put feelings aside and work with what we asked for. I think it’s our best-sounding record: what we’d found with Steve, which was finally finding clarity and feeling like everybody’s voice was heard, and then Chris just has some extra oomph in the way he mixes, but I don’t know what it is. It was really cool to come back and work with Chris because when we had worked with him before, we were very young. It was our first time in the studio. Although Chris was really great with us and for us, we didn’t know how to have our voices heard. In a way, we didn’t trust ourselves for our voices to be heard.

This time around, we better understood what we needed and what we wanted, and it streamlined the process. The communication was better between us the second time around. And it could have been really bad! [laughs] We asked a lot from Chris to mix in a certain way that he’d never done before. We asked a lot from Steve to let someone mix him in a way that had never been done before. It took a lot of graciousness and trust in us for them to do that. It was a really positive process.

Doing Rap Battles At 14 Years Old (1998)

Do you have any fond memories from when these rap battles happened?

HERRING: Rap battles when you’re young, it’s lunchtime in the cafeteria. I’m sure it still happens to this day, at least once a week. But cafeteria battles are where I started my short-lived career as a battle rapper, and gym class in the bleachers. It’s funny because it’s really where I had my first moments of, other than singing in school assemblies and stuff like that, having an audience around me. Probably by 15, I got on stage at a benefit show and freestyled. I wasn’t really a battle rapper; I love to just freestyle.

By the time I was 17, and then 18 and 19, I entered some competitions. Nothing ever got that far, but I’d get props for being a young kid and coming up and trying to battle, but I probably only won a few actual rounds in the five or six battles that I entered. Maybe a couple more than that. I made it to the finals once when I was in college. That was the last time I battled, and then I was like, “I don’t think I’m really built for this thing.” But it was definitely a thing that I really loved and enjoyed. It made me feel crazy in the sense of that rush of adrenaline, that rush of emotions and the way the fear of failure ends up being the fuel.

There was one time, it was [my friend Abe’s] final year of high school. There was [a rap battle], and he was at a different high school than me. I was really feeling myself at the time. I had recently battled some kids at a football game that had come to our high school. It was a rivalry game. A few months later, it was our school playing at their school in a basketball game. I didn’t have a crew or anything that I rolled with. I just rolled up to the game. I found my buddy, and then it was like, “Where’s the best MC? Who’s the best guy at the school?” And he made it happen. Then I proceeded to get completely destroyed and booed out of the gym. People wouldn’t even let me speak. They were just booing me. This guy just ripped me for two minutes, and I wasn’t fazed until I started to rap and was getting booed. You couldn’t hear what I was saying. And then the crowd just booed as they walked away from me. I wasstanding there, mouth open.

After that, it took me about five or six months before I could freestyle again. I’ve never really experienced anything like that. What’s interesting to me is the way that it completely destroyed me. Getting beat really bad in a rap battle is extremely emasculating. I was like, “I don’t think I should ever do this again. I don’t think I’d ever get on a stage again.” I’m glad it eventually went away.

Were you using the Hemlock Ernst alias back then? Or were you just rapping as Samuel T. Herring?

HERRING: Hemlock came as a name that I used to post on the Ozone music forum. Back in 2000, Ozone was a short-lived record label out of New York, and they put out Antipop Consortium’s Tragic Epilogue. I don’t know if El-P was involved. Ozone was like a precursor to what Def Jux became. If I talk to an old New York City head, like billy woods, he knows about Ozone’s forum boards. When I was 14, I posted one of my first poems there, and I got props. I had to pick a username, and the poem was about Socrates and drinking the hemlock poison. So I signed it as Hemlock. That was my early writer name, but my graffiti name was Psalm. I was 14 going around calling myself Psalm the Prophet. That’s how big-headed you can be when you are a teenager: “Yeah, I’m Psalm the Prophet. I’m 14. I know stuff.” [laughs]

It’s funny to look back on those days, but there was Hemlock. When Gerrit and I got to college, I met William and we started a band that Gerrit would join called Art Lord & The Self-Portraits, and that character’s name was Locke Ernst Frost, the self-proclaimed German Lord of Art. It was taking the names John Locke, Max Ernst, and Robert Frost. It was these ideas of religion, art, and poetry in a character. After Art Lord and in the beginning of Future Islands, I started writing again, and it became Hemlock Ernst. That full title probably came around ’08 or ’09 when I would first perform under that name.

Art Lord & The Self-Portraits (2003)

You mentioned Art Lord & The Self-Portraits, which is the perfect segue because that’s what I want to ask you about next. This was a performance art band. Is that correct?

HERRING: Yeah. Well, it was a performance art piece, and music was the medium essentially.

What was the performance element of it?

HERRING: Well, back in those days, I had very large sideburns and an Amish beard. I had a full head of hair back then [laughs]. I used to slick back my hair. I’d wear a white tux and white pants, or, in the early days, I wore a white chef’s jacket that was tight-cut with white pants, and I spoke in a faux Eastern European accent. Our goal was to be like Kraftwerk, where the guys were all in black with long-sleeve turtlenecks. The idea was I was the German Lord of Art. I was [speaks in an over-the-top German accent] from a little town in Ohio called Germany.

I would say, “I’m from Germany. It’s a little town in Ohio.” [laughs] It was supposed to be a social commentary on how we treat celebrities, rock stars, and famous people in general: how they can be terrible and we still love them. Originally the Art Lord was very arrogant. He was narcissistic and arrogant. I mean, worse than arrogant. [Back in Art Lord’s voice]: It’s hard being the best if no one understands how wonderful I am!

The funny thing about it was that the character who was rude to the audience was very quickly loved, and people were like, “I love this guy who’s so rude to us.” The character did change a little bit. It became more tongue-in-cheek because we knew that people enjoyed it, but it also proved the social commentary that we were trying to say. Like, “This guy’s a prick, and we love it.” But yeah, it’s the story of Pygmalion and Narcissus. So the Art Lord had gone away when he was 18 because the limelight was too great. He returned after 20 years away painting the most beautiful thing in the world, [in Art Lord’s voice] my own face! [laughs] He wanted to sing his songs of woe to the world, but there were no musicians good enough to play for him. So he brought his favorite self-portraits to life.

In the early days, Gerrit played the drums on a drum pad and a little Yamaha. So he was playing keys and playing the drums on this tiny Yamaha, on a stolen lunch tray from the cafeteria. He had duct-taped a keytar strap on. We were just kids having a fun time, and it was very punk in the sense that we didn’t have anything; we borrowed instruments from other friends and started a band, and people really liked it. We became one of the bands in town that would play the local bars and stuff. So it was fun.

This is the band that became Future Islands, right?

HERRING: Yeah. The first four or five albums we made were seven-to-eight-song albums; they’re only CD-Rs. This was before we ever got anything pressed. Our first single for Future Islands was the first time we got pressed. But those days, every five or six months, we would put out another CD-R of songs that we recorded in our living room of one of our houses. At some point, it started to get a little bit more substantial. We became better at what we were doing. I’m proud of what we were able to do as kids.

Do you recall a turning point like when one band morphed into the other?

HERRING: Not really. The weird thing about Art Lord is that when we started Future Islands, we took a giant step backward. We had a new drummer, and we’d never had a drummer before. Art Lord was Euro synth-pop and Euro dance, and then we immediately became a synth-punk band. It was super fast and punky. There was no backing track.

To me, Future Islands became what we are today when we moved to Baltimore, and that would be the first sessions that we had once Gerrit got to town. It was the first time that it was just me, William, and Gerrit; the original drummer had left the band. We didn’t have a drummer anymore. It was the first time we were writing as a three-piece. That’s when we put our heads down and said, “If we’re going to do this, then we’re going to do it together. We all have to be accountable for what we’re doing.” That’s when we started to hit our stride with the band. But that was a few years later: two-and-a-half years into Future Islands and almost six years into our writing relationship together.

You were already pretty seasoned working together, too.

HERRING: Yeah, but that was the funny thing. If we kept writing as Art Lord and hadn’t shifted the formula with the drums, we would have had a more straight line into that period. The drums added this propulsion that we’d never experienced before. As Art Lord, I used to do the robot on stage. I would rock the mic stand, and I did some classic mic-stand moves, but I would end up breaking into the robot. The movement was very different when we became Future Islands. We were this punky synth band all of a sudden. There wasn’t a mic stand anymore. I felt the drums pushing through me, so I got more animated. But then what happened was the drums went away. Then I was like, “I still want to bring this energy.”

Personally, I don’t know if the way that I perform now would be the same had we had not had that drummer at the beginning of Future Islands. It was really formative for me to become what we do as a stage show now, which is trying to bring that propulsion and intense energy and emotion into the performance. It’s true emotion because the Art Lord allowed me to be melodramatic and mask the emotion. I didn’t have to own it. I could be saying something that I actually personally felt: about feeling isolated from the world; feeling misunderstood. I could play it off like, “Oh, that’s the Art Lord.” With Future Islands, I had to really own that. There wasn’t a mask. There wasn’t an accent. There wasn’t an outfit. It was just like, “This is who we are.” So it was all part of the process.

“Seasons (Waiting On You)” (2014)

We’re gonna skip forward to what I and many other people consider your breakthrough moment, when you guys started getting a huge audience, which was “Seasons.” When you guys were writing that, did you feel like it could be like your big hit?

HERRING: Yes! Back in those days, this would have been probably early- or mid-2013, I used to carry this big tabletop, conference-style tape recorder, like in the old days if you wanted to tape a meeting around a big table. I used to carry one of those around and press record when we were playing. I’d get home and, if I had the ability to, digitize it into my computer. But basically, the guys made this song and wrote this A-B, verse-chorus thing, and I was like, “This is really good.” I went home and I sat with my tape. I rewound it, and I pressed play, and 30 minutes later, I had written the song. So I digitized it, did a gruff vocal pass and sent it back to the guys probably an hour after seeing them. I wrote them and said, “I think this is the best thing we’ve ever written.” They didn’t think of it like that. [laughs]

I was like, “No, I really think this is the best thing we’ve ever written.” They’re like, “OK, cool. On to the next song!” At that time, we were just banking songs for a record. But that was an exciting one for me personally. Any songwriter will tell you some of the best songs are the “30-minute” songs, the ones that are immediately written because it’s almost like you’re channeling from somewhere else or they’re meant to be there. It’s like the guys found these chords, and there was something going through me that day that needed to come out. Of course, there are songs that I love that took me years to figure out. Then there are those songs that just come, and “Seasons” was that way for me. But three or four weeks later, Gerrit brought the instrumental for “A Dream Of You And Me” and I was like, “This is our best song!” [laughs] “Seasons” is an amazing song, but I don’t think it’s the best song on the album. I actually think “Dream” is.

Were you guys nervous at all regarding the new audience you’d bring into the fold with Singles?

HERRING: No, we were ready for it. When the album came out, it was two or three weeks before my 30th birthday. The interesting thing about that time period for us was that we had all made peace with what we had within music. We had realized, after years of touring, that we finally were able to pay our bills and not work second jobs. We were finally able to take time off the road to write an album instead of having to write songs in between tours. Everybody got to spend time with girlfriends or loved ones for the first time in the year that it was written and recorded.

Five years before that, it was all a struggle. With In Evening Air and then On The Water, we’re like, “Why doesn’t anyone care?” You’d get a couple write-ups, and then it would disappear. We saw that it was a steady growth. It was a very organic growth over the period between Wave Like Home to In Evening Air to On The Water. We were banking on the fact that [Singles] was going to be a step up, but we thought it was just going to help us and not be a big thing. Then Letterman happened, and it exploded. When I was 26-27, I wanted that exposure really badly. I was about to be 30, and this record’s coming out. I’m like, “Man, we’re really lucky that we were able to have a really natural progression and organically grow as a band without the pressure of a spotlight on us.” Some artists get swallowed up young, and then they don’t know how to deal with that pressure. I went from being like, “Why does no one care?” to “I’m glad that we were able to build our audience in a natural way.”

None of us really expected the big blow-up. We all expected things to jump up a level or two, and then they jumped up six or seven levels instead. I do feel lucky that we were able to have that moment. I don’t really remember those years much because we were working so hard. We were taking every single offer, every show, anything that came in. By the end of it, we hit a wall and really needed a year of rest. But we just went and made another album. [laughs]

That Legendary Letterman Performance (2014)

I’m sure you’re tired of talking about this, but Letterman was such a huge moment for you guys. How do you feel looking back at this performance?

HERRING: It’s crazy that it had such an impact. I understand why it had an impact on people. At first, it was really hard because the performance became polarizing, which is a sign of great art. When you polarize people, you create a fire of people who are saying, “This is amazing” and “This is shit.” Those people fight, and that fight becomes the conversation. The fight becomes the conversation of people who are championing it and people who are trying to tear it down.

I think it just speaks to people in a different way because then people have to see it, like, “What are people talking about?” So we were surprised, and the label was surprised. They didn’t expect it to be much of a thing. We didn’t even think it was going to happen ’til we did it. Even in the performance, I’ve said it before in interviews, I don’t remember actually performing the song. I was so overcome with the moment that I blacked out. I was in an internal dialogue in my head that was like, “Is your zipper up? Do not slip and fall! Are you going to growl? No, you shouldn’t growl. Are you going to growl? Maybe a little bit!”

Some people think it’s pure comedy. Some people think it’s pure trash. Some people think it’s great art, but it doesn’t matter if 100 people say that it’s great art if 100 people say that you are an idiot. a weirdo, or a cokehead, which was probably the most hurtful thing I heard: “This guy’s on drugs!” I had a drug problem, and I’m not on drugs. I’m clean, and now you’re accusing me of a thing that actually hurts me personally because that’s not really something to joke about. Years later, I would accept how much it helped me and my life and the band. It was a life-changing moment, and it took me years to see the way that it opened up my life. There is something about toiling in obscurity that’s comfortable. Even being a band that can sell 10,000 records, that felt really good.

I felt comfortable within that. When you have to step outside of that, you’re up to the scrutiny of more people, and things get uncomfortable. It can be really scary. There were a few years where I felt misunderstood and a little scared. Then I was like, “What is this? You say that art is about sharing yourself. This is who you say you are, so you need to be strong and have conviction for your art.” There’s so much good that came out of that and so many people who were able to discover us, and people still watch that video.

I rewatched it just the other day in preparation for this. You’re such an engaging live performer. You said you almost blacked out during it, but usually when you’re performing, what are some of the things that are going through your head?

HERRING: “Is my zipper up? Do not fall!” [laughs] It’s the same thing. The best performances do come from those moments when you are in that state of transcending onstage, when you’re connecting with something that’s different from yourself. You’re channeling something. You’re connected on a different frequency with an audience, and with the music, and you’re not thinking at all; you’re just breathing the piece. Sometimes, I have to remind myself to allow myself into that space. It’s very easy for me to disengage from the songs and work on the performance of the songs. But the thing is, if you remain engaged in the songs and the storytelling, then the performance is what you bring across. If you’re like, “I need to do this big thing here. And I need to do that,” then you may miss the emotional point of that moment.

It’s the same idea of the medium is the message. The way that I perform comes from playing in bars and house parties where no one can actually understand what I’m saying. I really care about these stories that I want to bring across, but no one can hear them. So I used to have to act them out. I used to have to show that emotion. Then that became a part of my understanding of performance: engaging with those stories and trying to bring them across onstage. As the stages got bigger, I was like, “Well, I need to make the actions bigger and the emotions bigger.” For a while, I didn’t realize this until last year when I acted for the first time, I learned about making things small. For a camera, you can’t do these big, sweeping motions.

Everything has to be very measured in small moments, and it made me connect with my emotions to do that. When I went back onto the stage, I felt myself reengaging with a part of me that I had forgotten about, which was where a lot of my strength originally came from. It made me respect the songwriting more and get back to those moments of connecting with these original stories to bring real emotion. I think it’s easy to perform, but when you’re connected, then you get to that transcendent state. You’re filled with a joy of true communion with an audience and with your art that’s hard to explain. I’m sure people have all kinds of things like that, like running or cooking. Everyone has a thing. For me, it’s that connection to an art which is like a deeper form of myself that I can’t touch.

Trouble Knows Me, His Hip-Hop Project With Madlib (2015)

What did you enjoy about working with Madlib?

HERRING: Well, I have a treasure trove of unreleased Madlib beats on my computer. So that’s pretty cool. I think I have, like, 800 tracks. I’m sure a good portion of them have come out now. But that was a really cool experience and an honor to be able to do something with him. When people ask me what he’s like, he was like this calm Buddha figure: smiling, radiating. He was a real joy, a humble and quiet guy. The music speaks for him and his life. I’d written a bunch more and things didn’t align. I wrote an album that we never got to put out. I’m sitting on 200 songs that are never going to come out.

There was a thing that happened to me a few years ago, though, where I had a collaboration with DJ Shadow, one of the heroes of my youth. It was such an honor to get asked to do something with him. He really pushed me. I sent him the first demo. He was like “That’s not it.” I sent him a second demo, and he’s like, “Better, but work on this.” I sent him a third demo. I sent him a fourth and fifth, and we got to the sixth demo. He’s like, “OK, that’s the song.” He really made me push myself, and it made me realize that these songs don’t have to be so precious. He helped break my ego down. When you’re doing features, which was another important lesson, it’s like, “This isn’t mine.” He’s asked me to fill this place within his record. I’m honored, but also, this is his record. He should be in control, and I should trust him. And of all people, it’s DJ Shadow. I trust him with directing me.

That experience became extremely informative to me as a writer and helped me let go of things and hold on to these demos. Sometimes you’ll be like, “I wrote this great line. I don’t want to leave it in this song. It’s never gonna be released. I’m not gonna give this person this thing.” You’ll find that in rap features. People don’t always give their best work because it’s somebody else’s stuff. But you should always bring it! That’s the thing that I’m getting to: This doesn’t have to be precious. As long as we’re working and creating, these things are going to come. They’re going to pass through us, and we just gotta grab them and take them, and then we can build on them and throw them away. It’s not the end of the world.

With both Madlib and DJ Shadow, how did you guys link up with each other?

HERRING: With Madlib, I got to know him through his manager, Egon, at the time; he was also a DJ back in the day. The guy that signed us to 4AD brought him backstage at a show. We played in LA in 2014. I met Egon, and I was like, “Oh, you’re Egon. I have your record.” He’s like, “You don’t have my record. I’m not a musician. I do management. I’m a record label guy.” I was like, “No, you’re Egon, right? I have your record, Curse Of The Evil Badger.” He’s like, “Are you serious right now?” Nobody has that.” I feel like he told me they made 1,000 copies of it.

Egon and I started talking about hip-hop backstage after a show. I’m covered in sweat, but I’m excited to meet him and talk about rap music. It’s been my passion since I was a kid. We kept up communication afterward. I was like, “Yeah, I rap, too.” I sent him some demo stuff, and he was like, “Oh, you’re actually a rapper.” Basically, we started a friendship. Then he told me that he was going to send me some stuff and maybe we could collab. He’d hook me and Madlib up. We made some tracks and put out a little record. With DJ Shadow, he reached out to me. I’m not actually sure how he got my contact, but I got an email from him one day introducing himself. I was like, “Oh, this is crazy.” Endtroducing….. was a really important record for me when I started discovering hip-hop. That record was a big part of my teenage years.

Covering Wham!’s “Last Christmas” (2015)

HERRING: We recorded that song in 2011 just for fun. Some friends of ours in Baltimore used to do a CD sampler that was a big call for songs that would go out to the city mailing list every year. We were always on the road; we never did anything. One year, we’re like, “Let’s give them a song.” So we did a version of “Last Christmas,” and it was a fun thing. It was really hard. George Michael has one of the most crazy voices ever. I could never hope to match him in his register, so I had to do my own spin on it. Recording that song, I had to really study what he was doing in the background vocals, and he does some crazy stuff. I had to record the vocals on my own in my room in Baltimore, and I was losing my mind trying to hit these notes toward the end of the song.

Is this your favorite Christmas song?

HERRING: Yeah, it’s probably one of my favorite Christmas songs. I’m trying to think of what my favorite Christmas song is… Maybe it is my favorite Christmas song!

Literally Going On A Run In The Video For “Ran” (2017)

HERRING: That was one of the dumbest ideas I ever had.

How did you come up with the concept for this video?

HERRING: The concept was pretty on the head. The original idea was that the guys were in a room waiting for me, and I was running around the whole world with a green screen, and we’d put, like, the Egyptian Pyramids, the Eiffel Tower, and Big Ben on it. [laughs] The original concept was a bit goofier, and, as we got our buddy Albert Birney on board, it took shape. I really wish that I had worn a pedometer that day to see how much or how long I actually ran. I had not gone on a run in probably 15 years at that point. The last mile I ran was for, like, high school. I also have a torn ACL, and that music video actually destroyed my leg for a year with the damage that I did.

It was maybe a month before we went on tour for The Far Field, so it was a really stupid idea. Or I shouldn’t say it was a stupid idea because I thought that music video was beautiful. I thought it was really cool, but it put me in a lot of pain.

Right before you’re about to be in more pain on stage every night! So, you’re not much of a runner and still did the video?

HERRING: I really can’t run because my knees are so bad that it’s the doctor’s orders. I mean, what I do onstage I’m not really supposed to do either [laughs], but running has a pretty high impact, which I’m not supposed to do. That was already my rule for myself. It hurts to run. Also, when you don’t have an ACL, you either can’t stop, or you don’t think you can stop, so it’s even trickier. You don’t even want to chance it

Being Interviewed By Andy Samberg (2017)

This goes back to when we were talking about Letterman earlier. You told Andy that the Letterman performance is your “Dick In A Box” and that it will be your epitaph.

HERRING: Did I say that?? [laughs]

Yes! [laughs] So, do you agree with your past self?

HERRING: First off, I do agree that it will be our “Dick In A Box,” but I also hope, for him, that it’s not his own “Dick In A Box.” I think he’s done better. I think he’s gonna be OK. I don’t think that’s what he will forever be known for. But I can’t believe I said that! He was a very nice guy.

How did you guys even get paired up together?

HERRING: Which outlet was it for?

It was for Magnet.

HERRING: Yeah, one of Magnet’s features is having cross-disciplinary talks, and they thought it would be funny to have the Lonely Island and Future Islands together.

Wow, I did not even think about that.

HERRING: Yeah, like, two people who have something in common, but they’re from different worlds, so that was cool. He’s married to Joanna Newsom, who I’m a huge fan of, and The Milk-Eyed Mender was such a big record for me for many years. She’s a brilliant musician. So there’s a deeper crossover.

You guys asked about Joanna Newsom in that interview.

HERRING: I think we asked him how many harps she had.

He was just like, “A lot of harps!”

HERRING: Oh, so many.

Is the fandom mutual? He said he’s a fan of your band. Are you a fan of stuff beyond “Dick In A Box?”

HERRING: I’m a fan of Andy Samberg. I haven’t really gone deep into the Lonely Island’s music. But I enjoy him as a comedic actor. I think he’s really funny. I was a big fan of Hot Rod. That movie killed me. Because we’re Southerners, Danny McBride was a hero in all those movies, always cracking us up.

Back At The House, His Debut Rap Album (2019)

What was the timing like for this? Had these songs been around for a while and you were waiting for the right time to put them out?

HERRING: Back At The House probably got pushed back a year because I was on the road so much that we couldn’t finish the vocals. I have to go back and look at the original song files to see what the last song was. I eventually had to make time to go to Kenny Segal’s house, and we laid down the vocals over a few days. I was on tour for all of ’17 and ’18. Then I was living in Sweden for most of 2019. I don’t even remember when we finished the record. I feel like once we finished it, it came together pretty quickly.

The first song I wrote for that is called “Slabs Of The Sunburnt West.” I think that was written in late 2014. It might have been the very beginning of 2015. I met Kenny through R.A.P. Ferreira when he had reached out to me about doing a feature on the song “Souvenir” for his album, so the final outcome was under Milo, and it was a collaborative record between Kenny and Rory.

I was not familiar with Kenny, and I was not familiar with Rory before he reached out. It was just a kinship when we all met. Sometime after that, Kenny hit me up out of the blue, like, “Hey, I’m working on some new stuff.” I wrote that song very quickly, “Slabs Of The Sunburnt West.” He started feeding me stuff through 2015 and ’16, and I was off most of 2016. I spent a good amount of time in LA, so I was visiting Kenny a good bit. But in 2017, I went on the road, and ’18, we weren’t able to work together. He was like, “Hey, the whole record’s done. You just gotta record your vocals.” Sometimes, the hardest part for me is that last step of finalizing things because that’s when it really is out of your control. It’s also the most important step. I love making demos all day. But when I have to do the final thing, I get crazy anxiety because it’s going to have to go out into the world.

As both a vocalist and a rapper, what are some of the nuances that those two things may share and where they might diverge a bit?

HERRING: I would say you can do more with rap, which can be really freeing. At the same time, that can be a detriment, too, if you feel this need to rhyme. I mean, there is a whole new movement in rap that doesn’t rhyme, which is really interesting. But in that way, that’s a big difference. Sometimes, with a rap form, it can feel constrictive for me. Yet you can go so much deeper. The form of a pop song is 16 to 24 lines, and the form of a rap song, if you actually write a 16, it’s like 32 seconds. I always joke that I don’t write 16s; I write 27s because I need more time and space.

Especially if you’re writing something very personal, you can go really deep within hip-hop. You can do songs without choruses; you can make a minute-30 track; you can make five-and-a-half or eight-minute tracks; you can have things really shift. You can also do that within other singing forms, but not within a pop form. A pop form is a little more constrictive. A pop song has 16 or 24 lines. It’s all about, “Well, how do you say it all in that?” If that’s the puzzle of it, how do you make every line count? How does it lead you to a feeling? How do you set up? How do you set a scene or create a feeling with just three or four words, as opposed to being able to describe the room and sprawl out in a rap form.

If you so choose, you can also do a quick-shot style with rap as well, which is really fun to do. Of course, they have similarities, too. When I started writing for Future Islands, I was a rapper who didn’t know how to write a song. Overtime, I learned how to write songs. When I came back to rap, I was like, “Oh, now I’m actually saying things. I’m not just being a technically skilled rapper, tongue-twisting and fast. I’m actually saying something and turning a message because the songs that taught me the most about songwriting were rap songs.” “I Used to Love H.E.R.” by Common and “The Hypnotic” by the Roots. These were songs that taught me how to turn the knife and build this whole atmosphere in the story. And “Clear Blue Skies” by the Juggaknots. These were deeply emotional songs. The way that they work is probably more what people would think of as a standard folk song.

It’s the art of storytelling.

HERRING: Yeah, telling a story and doing that turn at the end. The average person doesn’t know much about rap music and thinks it’s this one thing, and it’s like, “No, these are great writers; these are poets.” So that’s what I got from it. But it took me time to learn to write a song and understand those songs in a different way to be like, “Ah, this is how you lay it out. This is how you pull the rug, twist the knife, and build feelings.” For me, they informed each other a lot, especially in the last four or five years. It made me a better writer on both sides, which is cool. As you get older, you hope that you keep learning.

Who are some of your favorite rappers right now?

HERRING: Well, the homie R.A.P. Ferreira. Armand Hammer, I’ve been following since almost the beginning. Billy woods has been my favorite writer in the genre for probably 10 years now. He sounds like gravity.

That’s a great description.

HERRING: I used to say that he was like a marble slab, but it’s more than that. It’s the weight of his voice and what he says. The way that he and Elucid work together, it’s both slippery and incisive, super fluid yet sharp and direct. They’re interesting, and I always think that the best rap duos can’t have two guys that sound the same.

Traditionally, I always thought that the best rap duos have the simple MC and the more abstract one, but I feel like they’re off of that. Between the two of them, it’s almost like woods is the simple MC in this equation, and woods is not a simple MC! [laughs] It’s like a heightened form and the same way Organized Konfusion has Prince Po, who is the simple MC yet so brilliant, but Pharoahe [Monch] is obviously the more abstract one in the group.

A guy that I’ve been listening to a lot is YUNGMORPHEUS. I’ve also really been loving Pink Navel [and] AJ Suede. There are so many people I’m trying to think of, but we’ll go with that.

Touring With Weezer And Joyce Manor For Weezer’s Indie Rock Road Trip (2023)

That is such a wild bill. How did you feel about touring with those two bands?

HERRING: We definitely stuck out, but it was a lot of fun. I didn’t realize how much Gerrit, one of my best friends through high school, knew Weezer. I did not know Weezer. I knew that William was a big fan. Mike [Lowry] was also a fan from back in the day. I didn’t really know them. But I have the utmost respect for those guys and the fact that they’re still going because it’s a really hard business. It’s a hard road to be able to keep doing what you do, and they put on an amazing show every night. We felt honored to get asked to be a part of that. They can have whoever, so we felt really honored.

We got to know Joyce Manor, as well, who were just really a lovely bunch of guys. That’s what the road is about. But for us, we’ve done very few opening gigs and tour support. We never got the offer, so it was very new to us. It was a new challenge because, opening for a crowd, it put into perspective what it’s like for people to open for us at times. We just assume, “Oh, we asked this band to play with us because we love them, and they’re gonna have a great experience.” But it can be hard when the front row is like, “We just want to see the band that we want to see.”

It was an experience that was humbling. The first week we’re like, “I don’t really know if people are digging this,” and you start to question yourself. Then you’re like, “I’m here for a reason,” and you begin to trust yourself again, like “Your favorite band did ask us to come and play!” The experience was one that I definitely learned from and went back to that feeling of believing in myself and trusting myself and building a trust within the band again, which is really easy to lose sight of when you are only playing to your crowd. You can get very comfortable in your performances. You can get very much like, “Oh, we’re just killing it.” It was good to step back and play in front of a new crowd and be like, “Challenge accepted!”

It put us in front of a bunch of people who wouldn’t have seen us otherwise, and that’s always a positive experience because you will reach people. We definitely did reach some people, and that’s what making music is about. If you’re gonna go into the world and have music and say, “I don’t want people that won’t like my music tonight here,” you’re just gonna have to stay inside and not release anything. Part of the game is accepting that your music is not yours once you put it out. The people who are going to find it will find it. You just have to trust that and believe in yourself as an artist. Ultimately, you’re making your art, which is what you see when there’s a band that’s like, “Wow, they’ve been doing this for 30 years. That’s amazing.” And it was not the music that bugged people. It was definitely me. [laughs] We were lighting up the Weezer fan pages: “What is this guy doing?” Like I said, it’s part of it. I had to accept that.

Acting In Apple TV+’s Series The Changeling (2023)

You’re discussing putting yourself out there and challenging yourself. This was your first time acting, and it was for a pretty big show. What are some of the challenges that you overcame?

HERRING: First, I had to learn how to act. [laughs] During my first year of college, I took an acting class, and I might have gone to it for four weeks before I decided that I didn’t want to go anymore. I got an F. I didn’t drop out of it; I just stopped going. I’ve entertained the idea of upstage acting. I love the idea of doing theater. But when I was in college, a couple of friends who were studying film would be like, “Would you be in my student film?” And these things were terrible! [laughs] It made me realize, like, “I’m not for camera.”

That’s what I got out of it: I’m not a camera actor. I love the stage. The stage is very freeing, and the thing about screen acting is it’s a lot of these imperceptible emotions that are shown in the face. You have to be small with your movement in the way that you show emotions. You can’t go big when the camera’s up close because it looks gigantic on the screen. So I was learning as I was going. But I like the stage because it allows for grand gestures, and then it was like, “I hope I can do this on a small screen.” I had six acting classes after I got the part, and I got cast because of a Future Islands show. We played the town that the writer of the show lived in in October of ’21. She was a big fan, but she never saw us play live. At the time, they were casting for the TV show, and they hadn’t figured out who was going to play this part. She came to her first Future Islands show and was like, “Oh, I think that’s the crazy asshole in the TV show!” [laughs]

So she brought it to me a few months later, like, “I’m writing this show. I think that you would be really good in this part. I know you are not an actor, but are you interested?” At the time, I was going through a breakup, and I had just gotten back from Sweden. My whole life was in an upheaval, and I didn’t know what was up and down at the time. I was like, “Maybe I’ll try something new. Maybe this is a new part of my life,” because if I had still been in a relationship in Sweden, I wouldn’t have done the acting gig.

I’ve been offered some other parts before, and not anything this big, but I’ve had some other people try to cast me in small roles in films over the last few years. I’m just like, “I’m not an actor,” but this one felt like a big deal. I thought that they just wanted a cameo, play-yourself vibe, or you pop in and you’re a little character for a scene, and then you’re gone.

On this show, you play a major character.

HERRING: Yeah, a major character! So she writes me, and then I write back like, “Yeah, I’m interested. Send me the script. I’ll read it over the weekend, and then we can talk.” I read through the episodes, and I was like, “Oh, this is a serious role.” And then I’m like, “Hey, this is great writing. This is amazing.” I took on the challenge. I started doing self-taped auditions. My ex is an actor, so I was used to helping her set up for the camera on white backgrounds and helping her run lines for auditions. So I knew how it worked, and I started to do it in practice. After a few days, I started to feel better about it. Eventually, it was really hitting on something. I got to a place where they really liked my tapes. They asked me to come out to LA and do it in person. That was one of the most nerve-wracking things I’ve ever done. I was literally shaking through some of it, and I’m not nervous. I’ve played to tens of thousands of people, and I’m very confident. But being in a room with the writer and the director and the casting director, I was just like…

Out of your element a little bit?

HERRING: Completely out of my element! I’ve never done anything like this before. I’m scared and nervous. But I did it there so they could film it in person. They said, “We think you’re great. But would you be willing to see an acting coach?” I’m like, “Yes, please help me!” I’m not gonna half-ass it.

You did say you’re a perfectionist.

HERRING: Yeah, so I’ve signed up to go after this. Now I’m invested. If you talked to me two weeks ago, I would have been like, “Sure, I’ll give it a shot. I probably can’t do it, but I’ll give it a shot.” At this point, I’ve spent two weeks doing this over and over trying to figure it out, and I feel like I’m getting somewhere. The time I spent with the acting coach over a week completely changed my confidence. I went back, and I taped one more time for them after the week, and they sent off my tapes, and I got signed off on. It was actually a pretty quick process. But then I was nervous about not being accepted by the other actors because I wasn’t an actor, and this was a big deal. I’d never tried acting because I was like, “Well, people work their whole lives to be actors.” It’s like if somebody’s like, “I play a little guitar. I’m gonna be a musician!” Yeah, you’re a musician. You play the guitar or the piano, but this actual life is a very particular thing. It’s the same with those creative arts. When there’s a really famous actor who decides to be a musician, my first instinct is, ugh. So I was putting that on myself. I was reflecting that on myself.

I felt like an asshole. But I met everybody, and I was like, “Oh, everybody is really sweet and kind.” Everybody was really supportive and helped me through the process. I became more and more comfortable. Then I was like, “I’ve been performing onstage for 20 years. I do know a little bit about this.” I understand catching light and visual angles. I did have to learn to play it small. One of my favorite things about that whole experience was the actual acting, but you do so little of it, unfortunately. So much of doing these shows, I would find, is waiting to act. The mental fortitude that it takes to get through filming is sometimes just the time spent alone, which is also something that happens when you’re on tour.

But when you’re on tour, you’re constantly moving, which creates a different feeling, even though you’re sleeping in the same place. The venues are not the same, but there are similarities, and you do the same thing. Every day, there’s still this forward movement, and you are in a different city. It’s a different coffee shop and a different breakfast spot, even though it’s all generally the same. When I was in Toronto for four-and-a-half months, I’m like, “Wow, what is happening?” There were weeks where I would work one day, but I would be on call in case they needed me. I had to work through anxieties and things like that. To get through the process, I’d be like, “OK, I’m going to my trailer, I’m going to bring a book, or I’m going to work on a song.” Then you’ll be filling your time with something positive.

You mentioned catching light and visual angles. Is there any other overlap between performing as a musician versus acting?

HERRING: There were things that were natural to me, like learning lines. So much of performance for me is so different because, with music, it’s your own work. It’s my own words, my own stories. I feel really comfortable going into those places because I completely understand them. I can show this emotion or say this thing because it’s true. It’s what I felt; it’s what I know. All of a sudden, I’m inside of a character and I have to inhabit a different set of senses and emotions, but the overarching emotions are the same.

My character is like, “My partner left, and I don’t know where my family is, and I need to find them,” and feeling this sense of loss and tragedy and trying to joke his way through it. There’s a whole other twist to the character, but I could relate to, like, “I just lost everything,” because I felt like I had just lost everything in my own life. So in a way I was able to do the same thing that I do within Future Islands, which is channeling my emotions, just using someone else’s words and being in a different body. There wasn’t a time I was as nervous as I was that day at the casting agent’s office. My first day on set, I was like, “Let’s go!” I was ready to get to work. I felt like I was prepared at that point.

My coach completely changed me and gave me confidence. The first day we met, he was like, “I watched your interviews. I watched your performances. You’re an actor! You just don’t know it. You gotta trust yourself and trust your instincts and your emotions. You have all this stuff. If you want to do this, then you just have to believe that you can do it.” I really believed him, and then it made me believe in myself, and I got more comfortable.

Would you be willing to act in something else? Or are there any upcoming roles that you’re allowed to discuss?

HERRING: No one has come calling yet [fake comical crying]. Now, it would be cool! I don’t know if there’s going to be a second season of the show, but that would be cool. I’m open to the idea, but I’m not going to Hollywood. That’s also a power play. It’s the same as me as a rapper. Because people know me from Future Islands, they don’t expect me to rap. Even though that’s my original art form and what I was doing for eight years before I was singing in Future Islands, I was still rapping. When it comes to acting, I’m able to feel really free because I don’t have the same skin in the game.

That’s the power to be able to be like, “Yeah, I’ve already got my thing.” Future Islands allows me to create, and so now I get to go toward another passion with hip-hop. Then I feel free with the acting. I felt like I was doing it almost more for the writer and the other actors than I was for myself, like I had more to prove to them than I did to myself. But also, if I suck, I’m not even an actor!

And the writer was scared up until the first day of shooting. After the first day, she was like, “I am so relieved!” She was like, “I was really nervous that you were going to be terrible.” I was like, “But we did all the stuff!” And she’s like, “Yeah, but there’s cameras, and there are all these people and makeup and all this stuff.” I was like, “That’s nothing,” and that’s a place where it helped me. I’ve been on late-night sets. I haven’t been on film sets, but I’ve been on TV sets. My ex is an actor, so I know a little bit about what she went through and the way the hours were. But it was so much harder than I realized! That was a big thing that I learned was like, “Oh shit, I’m sorry for all the times I was rushing you out of your job when you were like, ‘I can’t leave,’ and I’m like, ‘Just fucking leave these people who are making you sit there!’” Then I’m sitting in my trailer, like, I’m such an asshole. I totally get it now, and I would have never understood. I never would have understood unless I’d done it myself.

But having that power of, like, “I’m gonna do my best. But if I don’t do well and nobody wants to see me act again, then I’m fine.” That did bring an extra level of comfort to the situation, but I was still trying to prove myself and do my best because I didn’t want to let anybody down.