“Does love come around or does one come around to it?” That’s the question at the center of “High Hopes 3000,” Role Model‘s just-released new single, and the singer-songwriter says the idea frames his entire third album. Chuck Timely & The Hourglass (Aug. 7) explores his journey after a very public break-up with Emma Chamberlain, with its musical approach taking off from the rootsy, strummy, ultra-hooky pop of his breakthrough hit, “Sally, When the Wine Runs Out,” from his second album, Kansas Anymore. He’s been rumored to be in another relationship more recently, but he emphasizes that the album’s songs are about an “up-and-down period of being single.”
Role Model (born Tucker Pillsbury) hopped on a Zoom to discuss the new album, the Chuck Timely character he’s created in connection to it, and his upcoming film debut alongside Natalie Portman and Mark Ruffalo in Lena Dunham’s comedy Good Sex. Plus, he reveals that he’s killing off a stage bit that went viral over and over — his nightly gimmick of bringing out a fan (or, often, a celebrity, from Portman to Charli XCX to Reneé Rapp to… Al Roker) as a “Sally.”
What are you up to today?
I am packing. I’m going to Primavera [in Barcelona] tomorrow, and signing way too many vinyls.
When you sign the album cover over and over again, do you start second-guessing the artwork? Or are you appreciating your excellent choice?
No, I actually love it. It’s growing on me more every day. I’m sure maybe I’ll get sick of it. We’ll see. But I’m proud of it.
Tell me about the concept of the photo, where you’re hanging out next to newlyweds or whatever.
I had Chloe Chippendale, she’s the photographer. And I brought her this idea without really showing her any of the music. But I had the album, and we had this Chuck character. And the album’s themes… The common thread was about time and feeling a little bit stagnant in this two-year period of being single and dating and then not dating and feeling this pressure the entire time of, “All right, I’m getting older. I think I need…” — feeling a pressure to find love and all the questions that come with it. And I’m also now at the age where everyone’s getting married around me, and I’ve just started going to weddings as an adult for the first time last year. I wanted to represent this character that I came up with as well as the themes which he represents. He’s a little bit pathetic in a charming way.
How early or late did “High Hopes 3000” arrive in the process of the album as a whole?
That was close to the beginning. And I had that line, “Does love come around or does one come around to it?” I was holding onto that forever, and I was like, this feels like the question I want to set up the album. And once the song came and I wrote the rest of it, I was like, I feel like this should also just probably start off the whole rollout. ‘Cause I think that question sets up the album in a nice way and this journey that I go on to find the answer.
It’s definitely a “being single is not all it’s cracked up to be”-type song lyrically.
Yeah. It was a rollercoaster. You get sick of it a lot, and there’s moments where you’re like, “Oh, I love it.” But I think you really start to have these existential moments of, “What am I doing with my life?” Also, is finding love or falling in love going to fix whatever else is wrong here?
I do have to say that there are people who’d be like, “But being single as a young celebrity is probably awesome.”
I like it not for that reason. I’ve spent most of my life single. The part I like is being on your own time and really only having to worry about yourself selfishly. It’s a nice thing, but also, that can only go so far. I think it’s an important thing to learn how to take care of someone. And it felt like maybe it was a missing piece in my life.
There’s a Springsteen line on the Tunnel of Love album where he goes, “When you’re alone, you ain’t nothing but alone.”
Yeah, exactly. And I think there’s a thousand ways to write about it and I guess that’s what I did on the album.
Sonically, what was the vibe you were going for on the single? In the verses I hear Jackson Browne, and in the chorus I hear ’90s country. And the Jackson Browne part is interesting, because one of your producers, Mason Stoops, has actually played with him.
Yeah, I love that. Jackson Browne was a huge part of the album, across every song on the album. But it’s always riding a line and touching these musicians and bands that I love without someone easily being able to be like, “Oh yeah, this is just a cool new Jackson Browne song.” We wanna split it up, and so it was like, I wanted some of those stabby, yacht rock, Doobie Brothers, Hall & Oates keys, and I wanted the keys to lead it so that it wasn’t too country on the nose, and then obviously bring in a little bit of the Georgia Satellites and a little bit more rock to the chorus.
Yeah, when I heard country, maybe I was just thinking of “Keep Your Hands to Yourself.”
Exactly.
It’s interesting that you mention the yacht rock vibe. I’m a fan of the new Charlie Puth album, which has some of that same feel. Maybe that’s in the air.
Yeah. I haven’t heard that, but I love yacht rock. It was just taking little things. Those stabby piano hits always felt so pop to me in a way that people weren’t bringing into modern pop, and I think there’s so much genre blending you can do with that type of playing.
How much stress came in with the idea of following up a breakthrough album?
It really didn’t. I think maybe because “Sally” just taught me a lot. That song taught me a lot. I feel like I found a voice. I feel like that was the beginning of me finding this way to pull music I love and artists I love and turn it into modern pop music in a palatable way. And it just gave me a lot of clarity of how to move forward — not try and make a record of 12 “Sallys,” but it just felt like I found a cool road to follow now.
Is there going to come a time when the nightly Sally bring-out stops being part of the show?
I think I’m done. We have Primavera in two days, and I have no plans to keep that going. I think it’s good to know when to end a bit. If this album wasn’t good, I’d be like, “Yeah, we should probably keep the Sally bit going, I gotta sell tickets.” But I feel very good about this record, and I don’t think people will even give a shit, to be honest.
So at Primavera, you’re gonna play the song but just not bring anyone out? How does one swing that the first time?
I’m just gonna do it, and we will see if people start walking away or not.
When did you make this decision?
The last shows we did were in Australia back in February. And while we were on that final stretch, we were just talking about it, and I was like, “I think we don’t need to do this anymore.” I know, I feel in my heart when a bit needs to end. Because if we keep going, it’s just gonna die out and be this sad thing. The internet is very predictable. I think people are very predictable. And I just know these things have a short lifespan, so I’m gonna get ahead of it.
Does there need to be a new thing, or can you just play your songs and you’re good?
Yeah, let’s go back to when you can just play fucking songs. Listen, that was never a planned thing. We were never like, “Let’s do this thing to make the song blow up and get bigger venues.” It was just a happy accident, and I’m really grateful for it, but I’m not gonna be defined by being the dude who brings out Sallys at his shows.
When people heard you were going to Jack Antonoff’s studio, I think they maybe thought that Jack Antonoff himself might be involved.
Yeah, there was a mix-up. My wording was not smart. We also ended up leaving that studio after a week. I was getting way ahead of myself. But yeah, no, Jack Antonoff was not involved. I did the record with Mason Stoops and Taylor Mackall, who for their whole career were session players. And I was like, “You guys should be producers.” Taylor is a piano god, Mason is the guitar god. Let’s make a record.
People have been slotting you as a pop star, but I have feeling you’d prefer they think of you as a singer-songwriter, more like Noah Kahan, who I think is a friend of yours. He’s from Vermont and you’re from Maine, so there’s a New England thing going on, too.
I would love for him to be my friend! Friend’s a strong word. I love him, and we talk, and we have a lot of things in common, and anyone who shares a love of Maine, I’m like, “You’re my brother now.” But I agree. I love the challenge of pop music and what you can do with it. I don’t think I ever wanna be a pop star. I don’t think I ever want that label, but I love making pop music.
Tell me more about the album as a whole — the journey in making it and the sonic places we’re gonna be hearing from you.
Lyrically, the common thread seemed to be time. And when we started really figuring out how to produce it, it was like, let’s ride that a little bit and take little pieces of the best parts of all these eras that we love and pull them in to make these weird little cocktails of songs along the way as this journey through time. Which is where I came up with the Chuck Timely thing — someone who can represent that journey through time, someone who’s been there the whole time.
Is he almost an immortal dude who’s journeyed through all these eras?
We talk about him as a time traveler. This weird dude who was just for some reason in the background of all those studio sessions. We talk about Chuck every single day in the studio, and it was the most fun part, honestly. Once the songs were written, all we did was talk about Chuck. We made up all these stories. I feel he was always in the background of photos with Michael Jackson for some reason, but also weirdly knows Olivia Rodrigo and has been through this journey through the decades. And the idea was to have someone represent what we were trying to do with the album.
What were some other eras or styles that you visit?
Bruce Hornsby was a big one. And the other Bruce, of course. Fleetwood [Mac], a little bit of Fleetwood. But also, I love Madonna, and I had a weird obsession with her. Trying to apply the danciness of ’80s synth-pop music without using synths was another thing that I did on the record. I just had a rule of no synths on the record. And so that was a challenge. We tried to really learn from the Madonna stuff and see how we could apply what she was doing within our soundscape.
She’s really underrated as a pure songwriter. She’s one of the greatest pop songwriters of all time. But it sounds like it’s as much the vibe, the danciness that you were trying to figure out how to capture.
Yeah, ’cause that’s new to me. And that was the best part. It was, again, mixing in the same song, we’re trying to learn from Madonna but also referencing JJ Cale. And always trying to — if we’re going too far right in a certain direction, I’ll pull from the left. Another example is we have a song on the record that was always leaning the furthest folk that we ever wanted to go. That song is screaming for a fiddle and a banjo. And so instead of that, we added a flute solo and some other weird little sounds. It was always a fine line. We were riding a fence the whole time.
Where did your musical education come from? Was there someone in your life who exposed you to these older acts?
My mom — her music taste was always prime Americana. Jackson Browne, Neil Young, and Van Morrison were her top three, if I had to guess. And so I was exposed to that, and there’s a lot of nostalgia there for me. And then also working with Mason and Taylor — the reason I chose them is ’cause they just have so much more knowledge on these things. I think they filled the gaps for me and my knowledge and were able to, if I was describing a sound or a feeling, they would bring up an artist that I’ve never heard of. They put me on to a lot of the things that I ended up referencing.
You started out rapping in your really early days. Does any of that carry over to your current music, or is that just a dead end for you?
It’s a dead end. I don’t know who I was trying to be back then. I think in terms of my first EP, I guess it was similar in a way — I liked the juxtaposition of these sing-y choruses. It was prime time bedroom pop when that was happening, and it felt cool to bring a little bit of that into bedroom pop and mix this indie guitar-driven stuff with rappy verses. But anything before that, I’m just like, “Who was I trying to be?” I don’t know. What I was running away from or something.
What was the hardest part of recording this album?
I think the biggest challenge was just this line that I keep talking about that we were riding. I had this very clear vision from before I even started writing the songs of what this album is, and I’m really bad with communicating what I am seeing or hearing. And so it took a long time for Mason and Taylor to understand, and for us all to find this balance of things and not make this rock record, not make another folk Americana record — really trying to ride that line. For me to communicate these ideas was always the hardest part. But that being said, it was the most fun I’ve ever had making a record because every song just started with us jamming in a room. We’d call it stations, and we’d all go to our station, and we’d just start the day by jamming and being stupid. And I think you can hear the fun we had in the record.
Are you always on guitar? Do you play anything else?
I only play guitar, and I play it very poorly. There’s one song where we kept the exact lick that I came up with. There’s a couple songs where we kept my original chords. But I only know cowboy chords. My idea the whole time was, I’ll write a song on boring chords, and then I’ll bring it in to the boys, and they will use their expertise to make it more exciting and musical.
Without prying into your personal life, is the album a story of going from being single to not being single? Does it end in another place?
No. I wrote a lot of it during that time and it was just this up-and-down period of being single. And maybe there’s beautiful little moments where you think you found love, and then there’s little heartbreak moments along the way. I wanted it to feel like a journey through time with our boy Chuck.
Is there any sense in which Chuck is singing? Or it’s a looser thing than that?
I just don’t want people to think it’s a concept album. I already saw a few people being like, oh, what if this is an album about Chuck? It’s not. I wrote the songs. I wrote all the songs and then came up with this Chuck thing to just represent it. It’s as simple as that.
You’re done filming a new movie with Lena Dunham. What did you take away from that experience?
People always talk about how if you have a passion that you love, it’s really good to step out of that and go do something that scares you again for the first time. Music is this thing that brings me joy and nothing about it makes me really nervous anymore. So it was cool. It felt like I went and did something horrifying for the first time in a long time. And the payoff was great. I got to see it recently, and I’m proud. That is like a miracle that I was asked to be a part of that project.
So at least at the beginning, you felt totally out of your world?
It was horrifying. I hate feeling nervous. I hate feeling nervous, but it’s good for you, and it was good for me. And Lena is the best human being and she held my hand through the entire thing, so it was really fun.
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