In his debut album, Rx, Role Model was deeply in love. Now, with the release of his sophomore project, he’s still deeply still in love—but this time, it’s different.
In the nearly two years between albums, Role Model, also known as Tucker Pillsbury, went through a crushing breakup. His sound has evolved from dreamy bedroom pop, soaked in the wonder and vulnerability of a first love, to aching, country-tinged ballads that echo the heartbreak of losing it.
When his sophomore album, Kansas Anymore, first dropped, it served as a raw emotional timeline: the before and after of a breakup. First, the dread creeps in. You feel the unraveling—begging your partner to stay, berating yourself, bargaining for more time, desperate to fix something that’s already slipping away. Then, it happens. The fear of loss becomes reality. The devastation sets in. You’re awake in a world that looks the same but feels completely different.
Grief takes over like clockwork. Mornings become cruel reminders—you wake up at peace for a fleeting moment, then remember what’s gone. It crashes in, tidal and merciless.
But time passes, and eventually, so does the hurt. The pain lingers, sure, but it softens. You begin to move forward, not with forgetfulness, but with acceptance.
That’s where Kansas Anymore: The Longest Goodbye, the deluxe version of Pillsbury’s album, picks up. These new tracks continue to explore the complicated emotional terrain after heartbreak—when the tears are fewer, but the ache remains. They ask the question: what now?
The title track, “The Longest Goodbye,” was originally a solo effort, with the only feature on the albums’ standard release being the poignant “So Far Gone,” performed alongside songwriting powerhouse Lizzy McAlpine. With its plaintive banjo and gentle twang, “The Longest Goodbye” leans into country influences, evoking the warmth and melancholy of a Randy Newman ballad—think Toy Story’s “You’ve Got a Friend in Me,” but for the brokenhearted.
And just when fans thought the emotional journey was complete, Pillsbury surprised everyone with a second release: a reimagined version of “The Longest Goodbye” featuring none other than Laufey.
The pairing feels like fate. Laufey’s cinematic jazz stylings and ethereal vocals blend seamlessly with Pillsbury’s tender lyricism, deepening the track’s emotional core and turning it into a duet between two souls who understand the bittersweet art of letting go.
Laufey’s vocals don’t just add a tender, haunting quality to the track—they also shift the emotional perspective entirely. The lyrical changes introduce the voice of the one who broke Pillsbury’s heart. “Loving you’s like doing a chore,” she sings, with quiet finality. “Instead of blaming and bruising and watching what I’m losing, I don’t think I love you anymore.” Her words close the chapter, leaving Pillsbury with nothing left to do but let go. “And if this is my goodbye,” he croons, “it’s been the longest of my life. I see my shoes have been filled, and still, all I can hope is that he’s treating you nice.” It’s a farewell not of bitterness, but of grace; one that leaves with love, even in heartbreak.
With Kansas Anymore: The Longest Goodbye, Tucker Pillsbury doesn’t just chronicle the end of a love story—he invites us into the long, winding process of healing. It’s messy, it’s real, and it’s the most vulnerable he’s ever been.
But more than that, it’s one of the most beautiful portrayals of love I’ve witnessed in music. There’s something achingly human in the way Pillsbury writes about heartbreak—not with resentment, but with reverence. Every lyric feels like a love letter written after the fact, still laced with tenderness, even in parting. It’s the kind of goodbye most people dream of getting: honest, unguarded, and filled with an enduring care that refuses to vanish, even when the relationship itself has.
And, really, who wouldn’t want to be loved like this? To have someone hold your memory so gently, so publicly, that they craft an entire album about the impact you had on their life? Even if it ends in goodbye, it’s a love story immortalized in melody—something most people spend their whole lives hoping to experience, even once.
Pillsbury doesn’t just mourn what was lost; he honors it. And in doing so, he transforms heartbreak into something rare: a work of art that makes you believe love, no matter how fleeting, is always worth writing about.
And if this is his goodbye, I’m thankful he allowed us to have been a part of it.