Recently, Tucker Pillsbury, aka ROLE MODEL, has taken TikTok and the music industry by storm with his release of Kansas Anymore (The Longest Goodbye) on February 14. Off the deluxe album is “Sally, When The Wine Runs Out,” a song that ROLE MODEL teased online, resulting in the snippet quickly gaining popularity on TikTok preceding its release.

Who is Sally? And better yet, who is the person behind ROLE MODEL?

Tucker Pillsbury began his music career in 2016 at 19 years old as a student at Point Park University in Pittsburgh, PA. The now 27-year-old singer majored in film but broke his wrist twice during his freshman year at college — first at the hands of a skiing accident and then a skateboard accident — and found himself stuck in his dorm with music equipment that two of his friends left behind. There he recorded several rap mixtapes, learned how to use the recording software Logic Pro, and dropped out of school to pursue music.

Under the mononym “Tucker”, Pillsbury began rapping, soon releasing a mixtape called “Since When.” He then changed his stage name to DILLIS and self-released his debut album, Moth, in June of 2016.

It was in early 2017 that Pillsbury became ROLE MODEL, having switched from rapping to singing. The name derives from the dark period of Pillsbury’s life in which he first began making music. He started drinking and doing drugs — things that he “never did in high school” — and found himself turning into “the opposite of whatever a 'role model’ would be.” Pillsbury’s stage name nods to this challenging time.

Following the release of his debut EP, ARIZONA IN THE SUMMER in December 2017, ROLE MODEL saw his hard work pay off. Seven months spent recording the EP while wearing a cast on his wrist resulted in a rapidly growing fanbase and the attention of late rapper Mac Miller, who had heard the song “stolen car” off of the EP and invited ROLE MODEL to Los Angeles to collaborate. In 2018, Pillsbury signed to Interscope Records, a record label that boasts other artists such as Selena Gomez, 5 Seconds of Summer, and Maroon 5.

Pillsbury worked closely with Miller in Los Angeles, admitting to independent music magazine The Line of Best Fit that before their partnership, he had “never cared about anyone’s opinion that much.”

“I’ve never met someone and felt like they understood everything,’” Pillsbury said of Miller. “‘I saw myself in him … he was really one of a kind.”

Thanks to his record deal with Interscope Records, Pillsbury no longer had to record his songs in a cramped closet. Instead, he had access to a professional studio and the ability to make the music he wanted. ROLE MODEL’s second EP, oh, how perfect, was released in November 2019 through Interscope and Polydor Records with his first headline tour, the Far from Perfect Tour, beginning that same month. He followed oh, how perfect with another EP, Our Little Angel, in 2020.

Our Little Angel spawned the hit song “blind,” which soon gained popularity thanks to its upbeat sound, catchy hook, and ultimately its resonance with listeners. ROLE MODEL sings, “I've never seen something quite like you / I try to look away, but something's in the way / I think I'm going blind, I hope it doesn't change / 'Cause, I've never seen something quite like you.” ROLE MODEL’s expression of desire in lyrics earned popularity with listeners who have also experienced yearning and being captivated by someone.

It wasn’t just the music that won audiences’ attention, though. The online following that ROLE MODEL had amassed after the release of ARIZONA IN THE SUMMER continued to gain traction with the release of “blind.” His witty and charming online presence continued to grow his following; ultimately, the spotlight seems the perfect place for ROLE MODEL.

Online, Pillsbury entertains and interacts with his fans on TikTok. His alter ego account, saintlaurentcowboy, has amassed almost 500,000 followers and serves as a place for Pillsbury to post satirical content, poke fun at himself, and ultimately have fun. Pillsbury’s other account, rolemodel, is more focused on the brand of ROLE MODEL and is mainly utilized to promote his music releases, music,.

His highly anticipated debut studio album Rx was released in April 2022. Producing singles “forever&more” and “if jesus saves, she’s my type” and popular song “neverletyougo,” the album tackles what it feels like to fall in love and give in to the power of a woman — the woman in question, of course, being internet personality Emma Chamberlain, who Pillsbury dated for three years before their separation in October 2023. Their relationship and eventual breakup attracted attention to Pillsbury’s music from fans desperate to discover which songs were inspired by her.

Of Rx, Pillsbury said to Apple Music: “The album came together at the same time that I had fallen in love for the first time.” Later in the interview, he added, “For the first time in my life, I felt a change in my brain … It was much bigger than anything I had experienced.”

As Pillsbury continues to reach new levels of success, his artistry continues to evolve. His second studio album, Kansas Anymore, which was released in July 2024, embraces an Americana country sound. From track to track, Pillsbury establishes a soft, contemplative sound resulting from his celebrity breakup.

Opening track “Writing’s On The Wall” reveals a desperation to ignore the signs of a relationship reaching its end, while the indie-folk track “Look At That Woman” unapologetically explores regret upon loss. He acknowledges where he went wrong in “Superglue” with rambling lyrics.

Simultaneously, Pillsbury reveals the confliction one feels amidst a breakup — an unwillingness to let a relationship end. In “Deeply Still In Love,” Pillsbury accepts that the relationship has ended, singing, “I'm tryna play it casually / But it still bleeds / I'm sorry, but I'm deeply still in love.”

The album is reflective, reminiscent, and an art form of healing. In a 2024 interview with Vanity Fair, Pillsbury said of the album: “Once we started pulling out these singles, I fully started feeling like my own entity again, which is all I wanted.”

Before releasing the deluxe edition, Kansas Anymore: The Longest Goodbye, Pillsbury took to TikTok in early February to tease fans with a snippet of “Sally, When The Wine Runs Out”: “Heard through the grapevine, she can be a diva / Cold like Minnesota (Woo), hotter than a fever (Hey) / Aw, shit, here we go again, I'm falling headfirst / Ankles hit the two-step, Sally makes my head hurt (Hey).” Destined to be a standout track on Kansas Anymore: The Longest Goodbye, the song makes for a perfect cross-section of country and pop; it’s upbeat, fun, and perfectly captures the feeling of unexpectedly falling in love.

Another standout track from the deluxe is “The Longest Goodbye,” which pulls on listeners’ heartstrings with its showcase of Pillsbury’s vulnerable side. The song serves as a bittersweet goodbye to both Pillsbury’s relationship and the album with lyrics such as “Now you're changing and moving, I'll take my ass to Houston / 'Cause I don't think you love me anymore.” With “The Longest Goodbye,” Pillsbury closes his chapter of heartbreak by admitting that while he doesn’t think he’ll ever be so sure about anyone else, he hopes they both find happiness.

Like many other modern artists, Pillsbury’s notable online presence on social media — his TikTok accounts alone amassing almost 1,000,000 followers — has tremendously boosted his success. His early releases on SoundCloud allowed him to gain traction as he experimented with his music independently. Platforms such as Instagram, TikTok, and Twitter help Pillsbury connect with fans and showcase his laid-back, ego-free personality that naturally charms audiences.

In February of 2025, TikTok’s algorithm catapulted “Sally, When The Wine Runs Out” into popularity. Today, the song finds itself used in more than 200,000 videos on the platform, introducing ROLE MODEL to millions of new listeners.

Tucker Pillsbury: From Influencer to ROLE MODE