Tucker Pillsbury has spent years perfecting the art of the breakup song, but with “The Longest Goodbye,” he’s doing something entirely different; he’s saying farewell to an old version of himself while embracing something truer. The track anchors his album “Kansas Anymore (The Longest Goodbye),” released in February 2025, which adds four country-leaning songs to his already acclaimed sophomore effort. In the raging river of content releases this record is a few months old but we wanted to pull his journey apart a little as it feels very Wild Hearted!
The track is described as “a pensive, Southern-inspired acoustic post-breakup song” that strips away the glossy production of his earlier work in favor of something more organic and emotionally direct. The song feels like something you’ve heard over time (a classic) yet with a new twist – or a new expression of loneliness. My college English professor said a line that has stuck with me to this day which is essentially that each generation’s experiences are generally the same, but it’s that generation’s expression of those experiences that changes – this song is a manifestation of this notion at work!
Here Tucker talks about his loneliness of living in LA and his pulling need to get back home to find something more real which gives the record an understandable context. It’s a little long but it will give you the right perspective to listen to the record – at least it did for us.
And if you don’t want to listen to the full interview here he is celebrating his fans (from the same interview) and why he wanted pure vulnerability with this record in an effort to connect on a deeper level with his fans. When you hear this interview the song makes so much sense.
Personal Growth Through Musical Evolution
The deluxe album serves as Pillsbury’s way of “closing the chapter” but rather than wallowing in heartbreak, these new songs represent an artist moving forward and processing his experiences and emerging different – and hopefully stronger!
The response to Pillsbury’s some what country turn has been overwhelmingly positive. “Sally, When the Wine Runs Out,” an “upbeat country-inspired single,” gained popularity on TikTok as he channels his Jackson Brown on the track with a strumming guitar riff pushing the song along. The track opens with playful imagery: “Well I met Sally at a late-night dive bar / She don’t dance, but she downs her drinks.” The kind of character-driven storytelling that defines a great country song where it can feel fun and desperate at the same time.
Wild Hearted Take
What’s refreshing about Role Model’s shift is how natural it feels. There’s no fanfare or grand announcement, just an artist following his instincts toward music that allows him to tell more honest stories. The country and Americana influences give him room to explore themes that didn’t quite fit in his alt-pop framework, and the results speak for themselves. Sometimes artistic growth is about adding complexity, but in Pillsbury’s case, it’s about finding the confidence to strip things down and trust that the songs will carry themselves.
Stay Wild. Stay Authentic. Stay Whimsical
