‘Kansas Anymore (The Longest Goodbye)’ Review: Role Model Finds Closure, Sort Of

“Kansas Anymore,” released in July 2024, was a tonal shift for Tucker Pillsbury, who goes by the stage name Role Model. After a high-profile break-up with internet darling Emma Chamberlain, the singer-songwriter swerved genres, shifting from his rap-leaning debut “Rx” to the guitar-twanging, folksy “Kansas Anymore.” the album was a 13-track affair that scavenged through the wreckage of his past relationship for answers.

The result? A deft sophomore album that was poignant in its melancholia and regret. Particular highlights included “The Dinner,” a storytelling masterclass of LA’s insipid celebrity culture and Pillsbury’s homesickness for Maine; “Deeply Still In Love,” where an upbeat melody belies his unabashed yearning for his former beau; and “Look At That Woman,” where he gently notes that “I try not to call / But the leaves start to fall / Girl, it’s nobody’s fault / But, damn, you can make a thug cry.”

While “Kansas Anymore” plumbed the depths of Pillsbury’s heartbreak, it never quite found a satisfying close. In its final song, “Something, Somehow, Someday,” he confesses: “Yes, it’s clear to me, they’re meant to be / Something, Somehow, Someday.” On the listener’s part, it’s clear to us that Pillsbury isn’t ready to let go, even after the album’s excavation of his relationship — he seems content to continue indulging the delusion that he and his lover can, someday, find their way back together.

It is poetic, then, that we are introduced to a different Pillsbury in the deluxe edition of the album, released on Feb. 14. “Kansas Anymore (The Longest Goodbye)” chronicles his attempts to move forward from this chapter of his life. The four new songs released on the deluxe are similarly themed around nostalgia and lost love, but at long last, Pillsbury provides a fitting end to his album with a nuance that possesses a sobering, if bittersweet, acceptance.

Far and away the most anticipated track on the deluxe edition was “Sally, When The Wine Runs Out,” a song that went viral on TikTok in the days before its release. Drawing on the more upbeat tempos of “The Dinner” and the storytelling lyricism in “Something, Somehow, Someday,” “Sally, When The Wine Runs Out” certainly deserves its flowers. As Pillsbury starts the outrageously catchy bridge — “Aw, shit, here we go again / I’m falling headfirst / Ankles hit the two-step, Sally makes my head hurt” — it’s impossible to resist the urge to dance along with him. It’s an irresistibility which Pillsbury embraces in an accompanying music video, which simply features him dancing along to the song with wired earpieces in a shopping mall, much to the confusion of unsuspecting on-lookers.

Even so, Pillsbury remains cautious after his heartbreak, and his fear of getting hurt again adds nuance to the song’s simplistic lyrics. “Sally / That feeling’s coming around / Please don’t go falling in love / Then disappear when the wine runs out,” he sings in the chorus with an exhausted wariness tinging every word. The aftermath of his break-up continues to haunt him even as he moves on, a new dimension that adds to the emotional depth of “Kansas Anymore.”

But the biggest surprise among the new tracks is “The Longest Goodbye,” the song which serves as the album’s revised closer. Pillsbury takes on the persona of a bar’s final patron as he bids farewell to this particular relationship, watching his ex-lover move on with another man. “I see the new man you’re holding, the bar is finally closing / I don’t know what I’m buggin’ ya for,” Pillsbury sings. “I see my shoes have been filled, and still / All I can hope is that he’s treating you nice.”

The song is strangely reminiscent of the “Toy Story” track “You’ve Got A Friend in Me,” and its jazzy influences work shockingly well, a feat that speaks volumes to the production machinations of Noah Conrad and Mason Stoops. The twangy guitars meander with Pillsbury’s thoughts as he does his best to take stock of his emotions. “I don’t think I love you anymore,” he sings in the heartbreaking outro, “But I don’t think I’ll ever be so sure.” Pillsbury recognizes the necessity of moving on, no matter how imperfect the process may be, and it’s hard to think of a better way that he could have ended the deluxe.

“Old Recliners” and “Some Protector” round out the extended album. Although they are enjoyable listens, they do not hold the same emotional resonance as their two compatriots. “Some Protector” extends the metaphor in “The Longest Goodbye” of a bar’s closing time as Pillsbury ruminates about his inability to move on, “holding on from a distance” even as his previous lover is “holding on to someone new.” Pillsbury’s protracted recovery from heartbreak may be overly self-pitying in the hands of another artist, but his self-awareness and deprecation (“Am I dragging this forever?” he asks at a point in the song’s bridge) keeps the deluxe from becoming overly sentimental.

“Old Recliners” evokes the nostalgia of his bygone relationship: “I remember when the nights were long / Diving headfirst off the dock / Now I wonder where the days have gone / While I lay in bed and rot”. This retraces the same ground as “Compromise” and “Frances.” But ultimately, though “Old Recliners” and “Some Protector” are told from a place of greater distance than the emotions which Pillsbury lays bare in the original album, they fail to connote the same vulnerability and maturity of “The Longest Goodbye” or “Sally, When The Wine Runs Out.”

“Kansas Anymore (The Longest Goodbye)” was released on Valentine’s Day, a date surely too coincidental to be entirely unplanned. As couples celebrated love, perhaps Pillsbury provided a comforting soundtrack for those nursing a drink alone at a bar, learning to let go and making peace with their solitude. The road to acceptance, and closure, is always more winding than any yellow brick road — but with Role Model as a guide, it’s a worthwhile journey to take.

—Staff writer Angelina X. Ng can be reached at angelina.ng@thecrimson.com. Follow her on X @angelinaxng.