Role Model Reflects on ‘Sally’ Success, Therapy, and How Girlfriend Dakota Johnson Ended Up on His Album

As he gears up for the release of his latest musical chapter, singer-songwriter Role Model is peeling back the layers on his artistic evolution and deeply personal life.

With his highly anticipated album, Chuck Timely & the Hourglass, dropping on Friday (August 7), the artist—born Tucker Pillsbury—sat down with NYLON for an intimate discussion. During the feature, he opened up about how the songwriting process inspired him to finally begin therapy, reflected on the runaway success of his viral anthem “Sally, When the Wine Runs Out,” and embraced a refreshingly unfiltered version of himself.

Pillsbury candidly shared that conceptualizing and recording the record triggered a profound period of self-examination, ultimately guiding him toward professional mental health support for the very first time.

“Making the album and writing all those songs—I think me going to therapy now is a result of that,”

Role Model

he explained to the publication, noting that the creative journey encouraged him to examine his inner self through a much more profound lens.

This introspective body of work follows the immense breakout triumph of “Sally, When the Wine Runs Out,” which climbed onto Billboard’s Alternative Adult Airplay chart in 2025 and cemented itself as a fan-favorite milestone in his discography. Despite the track’s massive cultural footprint, Pillsbury confessed he never felt intimidated by the prospect of replicating its success.

“I love ‘Sally,’ and I’ll be performing that till I’m in a wheelchair,” he remarked warmly, before playfully critiquing his past penmanship with a laugh, suggesting that his self-imposed creative standards felt entirely wide open heading into this new era.

Expanding on the album’s thematic anchor, Pillsbury discussed the titular alter ego, Chuck Timely. Rather than serving as a distant, fabricated persona, the character acts as an artistic vessel to navigate complex motifs of romance, heartache, and personal awakening. The moniker itself has roots stretching back years, originating from a time when he briefly contemplated releasing music under the alias before ultimately settling on his primary moniker.

In a delightful surprise for fans, the singer revealed a very special contribution to the tracklist: his partner, Dakota Johnson, makes a spoken-word cameo on the song “Love I You” after spontaneously laying down the bridge during a casual visit to the recording studio. Though he initially hesitated to blur the boundaries between his romantic life and his career, Johnson enthusiastically stepped up to the microphone, crafting what he describes as an unforgettable collaboration.

Chuck Timely & the Hourglass arrives on August 7, featuring pre-released singles like “Joy” and “High Hopes 3000,” the latter of which made an impressive splash by debuting at No. 94 on the Billboard Hot 100.

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