Nick Carpenter, aka Medium Build, was working on “It’s Not Easy (Falling In Love),” a standout track on his fifth album King of Having Fun, with superstar pop producer Julien Bunetta when he experienced a midlife crisis of confidence of sorts. And he started to second-guess himself. As an artist who’d never quite fit into any specific genre, and up until then had never worried much about success or playing the showbiz game, he suddenly felt — as he’s amusingly mentioned in his own official press release — like a “washed-up thirtysomething.”

“The day I ended up in Julian’s studio, I was maybe a month sober,” says the 35-year-old Americana singer-songwriter, sitting at Studio City’s Licorice Pizza Records getting ready to perform for a packed store of fans of varying ages (an impressive turnout that proves he never had anything to worry about). “I had just been on a tour opening up for this pop boy that was blowing up [Role Model]. At the time it was like ‘Sally’ was just starting to go viral. He hadn’t fully stepped into his sleazy-dad rock-thing. He was really just still on the verge of trying to be ‘white boy who’s aware of Frank Ocean’ — which, hey, all of us fell into that for a while! … So, I came from the Role Model tour, and I’m like, ‘OK, whatever’s working, it’s not working for me. I don’t have these 20-year-old girls. No Medium Build fans are making TikToks. And that was what the labels tell me: They’re like, ‘We need your people to start making TikToks.’”

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Carpenter was already a critics’ darling with a devoted cult audience, but as he points out, “What [labels] notice is fanbases that go crazy and grow quickly. … My fans were kind of gatekeeping me. My fans are big fans, but they’re sitting in their room just listening to me and not really telling anybody. So, I’m like, ‘OK, how do I get the young people?’ And so, then my brain starts going to pander-y places. Do I need to lose weight? Get more tattoos? And I ended up in Julian’s studio. I’m a month sober. I feel like shit. I feel like I have nothing. And I’m like, ‘What do I do? You know Harry Styles. You know Sabrina. What’s wrong with me?’”

Carpenter expected Bunetta to tell him to do just that — shed some pounds, get some new ink, or undergo some other sort of glow-up to youthify his image and increase his Gen Z appeal. But, surprisingly and refreshingly, Bunetta offered the opposite advice. “He’s like, ‘No, you have experience. You can talk to the pain that these kids haven’t gone through yet.’ And so, that was a really empowering conversation, from a guy who’s seen a lot of eras of people and watched a lot of people try to reinvent themselves,” Carpenter marvels. “He’s like, ‘You can just talk from where you’re at. You don’t need to pretend to be young. You don’t need to pander. You have this wisdom.’ That was helpful for me.”

The result was what was Carpenter now considers the best and most important album of his career. “I’m just really proud of this record. I feel like I was present the whole time,” he gushes. “I don’t think I always had a plan; I’ve made music out of urgency, boredom, curiosity, playfulness, exploration. … Usually I’m just like, ‘Oh, here comes this urgent feeling. I’ve got to go to the piano and find it!’ And then I puke it out and I’m like, ‘Well, this is what I made.’ It’s kind of like the kid brings the art to Mom, put it on the fridge. Everything I wrote for years I would release. For this record, we really got a little more big-boy britches — like, everything we record, we’re not going to release. We’re going to really pressure-test them and see. I remember in high school hearing that they recorded 200 songs for Thriller and being like, ‘What? Only nine songs? They picked nine against whatever? That’s insane!’ But now I’m like, ‘Oh, that’s because they wanted it to be the best, with no skips.’”

Carpenter must be doing something right, because just a few days before playing Licorice Pizza, he performed at the Grand Ole Opry and part of that legendary Nashville venue’s ongoing 100th anniversary celebrations. He confesses that, as a longtime self-confessed “people-pleaser” who recently covered Charli XCX’s insecurity anthem “Sympathy Is a Knife,” he did suffer from imposter syndrome when he was on the same Opry bill as the Oak Ridge Boys and John Conley. He hilariously likens the feeling to being a Goth teenager at Thanksgiving dinner, when he “got up there and sort of yelled in my denim, in my little Canadian tuxedo.” And he once again felt like he should pander and “offer what these people like,” so he played the two of King of Having Fun’s twangier tunes, “Cone Off” and “Home Depot.”

“I didn’t grow up listening to country music,” Carpenter freely admits. “I learned about country music really intensely in college, studying songwriting in Nashville, and then I slowly began to see there’s this really deep world, that I had to excavate personally and find out what’s real and what’s good. … I was kind of trying to completionist and put my ears on everything in high school — I wanted to know everything — and then once I got to college, that’s when the streaming stuff really came about, and I was like, ‘I can know about everything!’ I can know about L.A. punk like X, and I can know about Northern England sad gray weather boy shit. And then I’m doing my homework on old country at the same time, because I’m in Nashville, and I’m like, ‘Oh, I guess I should know about Randy Travis and all the way back to George Jones,’ all the way back to Roy Acuff and all this stuff.”

Even when discussing serious subjects, Carpenter, a clever and self-aware lyricist, has a delightfully inventive and snarky way with words, often inventing “micro niche genres” that sound like Spotify daylist titles; along with “white boy who’s aware of Frank Ocean” and “Northern England sad gray weather boy shit,” he describes mainstream country bros’ sound as “eat pray, fish” and slacker Midwest rock as “Tuesday trip to the ATM to buy weed from your uncle.” However, his own music has always been difficult to categorize.

“I actually really do fuck with country music now, so it’s not fake, but I don’t make mainstream country music. But my indie rock keeps kind of rolling towards some twangy-type stuff, and so I find myself in these spaces that I do respect,” he explains. “So, if these people in this light, at this angle, at this exact moment, are like, ‘He’s country enough to play the Opry,’ then hell yeah, bro! I’m playing the Opry!” And he does think his organically growing appeal is a sign that he’s “a part of something” bigger going on in country music.

“I don’t think this is a diss or whatever, but sometimes you have to widen the tentpoles. If you really want to reach the next generation, you need to offer some alternatives. If the only thing that’s feeding country music is white guy trucker hat radio songs, then those are going to phase out eventually and you’re not going to have a base,” he says.

Carpenter, who was raised in an evangelical household and came out as queer five years ago, semi-cynically imagines record label meetings with TikTok-obsessed music executives saying, “‘We should get some queers and some Black people. And we should get some rockers in here.’ It’s sad, but you know that’s happening!” he laughs. “But yeah, I had a friend this week post on their story — this is a producer in Nashville who I think kind of sees himself as a bit of a gatekeeper — and he was like, ‘The Opry’s really letting anyone [play] this year.’ And I’m just like, ‘Oh my God. OK, thanks, bro.’ I just went ‘LOLOL’ — I commented as I was posting about my Opry debut.”

Now Carpenter is on a creative tear ( “I don’t even think I have enough time in my entire life to make all the stuff I want to make,” he says enthusiastically), and that coincides with his newfound sobriety. “I spent years on and off the wagon trying to figure out how to control this beast, because I love how alcohol made me feel,” says the troubadour, who actually used to work as a bartender in Alaska, which didn’t exactly help him stay on the wagon. “I loved how it made me feel relaxed, and I loved how it would ease my mind and kind of push some of the dark, painful thoughts away. I started to see that I was doing some intense bargaining with my mental and physical health, and my shows were starting to take dives. My relationships were starting to take dives. I was starting to not be able to see what was important — or at least I could see it the next morning, but I couldn’t see it last night. It was on that Role Model tour that I was just like, ‘This is going to destroy me. I’m literally looking at the most beautiful sunset on the beach day and I have no joy. I gave it all to the night demons. I gave it all away and here I am feeling rock bottom.’”

That’s where those above-mentioned fears about being “washed-up” came from. As Carpenter, who acknowledges that the “lore” about his exploits and unreliability was starting to eclipse his reputation as a genuine talent, recalls, “The voice in me was like, ‘You’re shit, you’re trash, you have nothing left.’ It just felt obvious. It was like, if I don’t change, I’m going to die. Maybe not immediately, but I will. I mean, we’re all going to die, but I’m going to die faster than I should.”

After he had a panic attack onstage and called an emergency band meeting, Carpenter finally asked for and received help, and now he says brightly, “It’s been pretty good! I had a little fall-off last year, but I’m 11 months kind of dry, and I have a lot of friends that are sober now, and it feels like the only way forward for me. But now it’s exciting. It’s like every day feels kind of like a sandbox. What am I going to play in? What am I going to explore, instead of how am I going to push the feelings down? What am I going to discover?”

And so, the title King of Having Fun holds multiple meanings, some of them sincere and some ironic, but Carpenter truly is having the time of his life now. “It’s this sort of hero’s journey,” he explains. “I think what I was referencing [in that title] was I was a fun kid. I think there was a kid who was having fun before he found booze, but then I found booze and I became the ‘party guy’ king of having fun. So, there’s the performative king of having fun, and then… there’s the kid, the original, who didn’t need chemicals to do it, who could do it just with a bike and a Blockbuster subscription or whatever. And then there’s the kid who needs chemicals to do it. And now here’s this 35-year-old who’s like, ‘OK, shit, we’re back to square one.’”