Chartbreaker: How Role Model (And Some Famous Friends) Turned a Showstopping Live Moment Into a Breakout Hit

Something fortuitous happened for Role Model during the second North American stop of his No Place Like Tour live run on Feb. 27. Jake Shane happened to be in Dallas at the same time — and with some last-minute coordination, the influencer ended up onstage with the singer for “Sally, When the Wine Runs Out.”

“People loved it — like, lost it,” recalls Role Model, chatting while still on the road. “We were like, ‘Why not do this every night? We don’t need a cameo. It will be fun to do a Justin Bieber “One Less Lonely Girl”-type of moment.’ ”

Throughout the tour, Role Model has welcomed one lucky fan onstage to dance around with the artist during the bridge of the sun-kissed pop-rock song. At one of two sold-out shows at Los Angeles’ The Wiltern in April, he welcomed friend Reneé Rapp to play the part.

Later that month, when the 27-year-old made his late-night television debut on The Tonight Show Starring Jimmy Fallon, he scored an appearance from Bowen Yang for the role. The stunt resulted in viral social media moments, with the unintentional strategy helping sustain the song.

“Sally, When the Wine Runs Out” arrived on Feb. 14 as part of the deluxe edition of Role Model’s second album, Kansas Anymore. (As was much of the album, the song was co-written with close collaborator Noah Conrad, alongside Annika Bennett and Harrison Whitford.) The deluxe, titled Kansas Anymore (The Longest Goodbye), featured four new tracks — but “Sally” emerged early on as “something we could jump off of,” says Sam Riback, Interscope Geffen A&M co-president and head of pop/rock A&R. “We were like, ‘Here we go.’ ”

By early May, Role Model made his Billboard airplay debut when “Sally” entered at No. 36 on the Alternative Airplay chart. The song also cracked the top 20 on Hot Rock & Alternative Songs and reached a No. 12 high on Hot Alternative Songs.

Riback first heard of Role Model, born Tucker Pillsbury, in 2018; at the time, Benny Blanco had an imprint with the label called Friends Keep Secrets, and one of its employees tipped Riback off to the then-unknown artist from Cape Elizabeth, Maine making music in his college dorm room. “I heard this demo, which we inevitably put out, of a song called ‘Minimal,’ ” recalls Riback. “It just immediately captivated me,” he says of the stripped-down, hip-hop inspired indie track. Later that year, Role Model signed to Interscope Records. (He signed with Best Friends Music for management in 2020, though parted ways with the firm this April).

Four years after signing, Role Model released his debut album, Rx, in 2022, where he showcased an edgier look and more alternative sound. But Kansas Anymore took a turn towards softer, more Americana-inspired indie-pop and highlighted his sensibilities as a songwriter.

“People who have been listening to me since 2017 have gotten to watch me slowly figure out music,” he says. “When I put out [‘Minimal’], that was really the first song I had made. I didn’t know what I was doing. So I feel like, truly, I did not find my sound until Kansas Anymore. It’s something I’m proud of and it feels like the most genuine thing I’ve made, ever.”

After the album arrived last July, Role Model was eager to stay in the sonic world he had built. While writing the album, he had two “rough ideas that were not fleshed out” but fit into the same universe. So he saved them (they ultimately became “Old Recliners” and “Some Protector”). But as he toyed with the idea of a deluxe, he knew he would need more: “I don’t wanna half-ass it,” he remembers thinking. Weeks after its release, he started writing again, and out came “Longest Goodbye” and “Sally,” the latter of which he calls “a new ending to the chapter…I think that this song felt like a breath of fresh air in that way of, ‘Oh, there’s somewhat of a positive spin here.’ ”

The most fun-loving song to come from the Kansas Anymore chapter, Role Model says “Sally” is “based off some truth,” with the song detailing his re-entry into the dating pool. “Lyrically, it was me being hesitant and doubtful,” he says, “not being sold on someone.”

Role Model teased the track in the days leading to its release, and when he kicked off his No Place Like Tour dates in New Zealand/Australia in early February, added it to his set. “The very first time I did it, people were singing the words. It got louder and louder every show,” he says. “It was the bridge specifically, but it felt like a big moment in the set and the song wasn’t out yet. And that’s when I started to be like, ‘Oh, maybe this is bigger than I can imagine.’ ”

“[‘Sally’ is] an entryway for all these people to see what Tucker’s been building so sturdily over the past seven years,” says Riback. “He hasn’t skipped any steps and he has meticulously put together a fan base that I think is so onboard and along for the ride, wherever this goes next.”

In terms of the next onstage Sally, Role Model has his eyes on Kacey Musgraves, teasing that they’re on a few of the same festival lineups this summer, including Iowa’s Hinterland and Aspen’s Up In the Sky, both scheduled for August. “There’s gotta be some strings we can pull,” he says with a laugh. Riback adds: “We are always planting seeds and hoping things bloom into what we would like them to bloom into.”

In between legs of his tour, he’s also been writing a bit: “I finally had some days to lock myself in the studio again,” he says, “which was incredible and inspiring in itself.” But, much like his career, Role Model is not rushing a thing, calling his rise “a very slow incline — with bumps, of course.” He admires the way his tourmate Gracie Abrams, for whom he’s opened, has navigated her own career, saying she is “an amazing example…I feel like she has just skyrocketed and has handled it incredibly.

“It’s always scared me, the idea of a moment and a giant peak in a career, because it’s the hardest thing to keep up with,” he continues. “And I think oftentimes, you see it go away. So I’m trying not to live in it, but at the same time, I’m doing everything in my power to make sure it does stick around.”

This story appears in the May 17, 2025, issue of Billboard.