Role Model’s rise to stardom and a reflection of his rebrand albums
Role Model, Tucker Pillsbury, Saint Laurent Cowboy, Chuck Timely and Sabrina Carpenter (for the chronically online fans). No matter what name you call Pillsbury by, there is no denying how much he’s grown as an artist and how significant he’s becoming in the music industry. With all of his rebrands, it’s never too late to become a fan and there’s always something new to look forward to. He just began his newest tour, “Chuck on Tour,” with stops in 26 cities across the U.S. and multiple countries, and tickets are still on sale.
“Chuck Timely & the Hourglass” is a unique, country/indie pop album with a lot of Pillsbury’s personality shining through. It delves into the ups and downs of relationships in your 20s along with the emotions and existential feelings that come with growing up and getting older. He reflects on a very developmentally important period in his life and the way he navigates it. Pillsbury has a way of oftentimes combining an upbeat rhythm with lyrics that are devastatingly emotional.
One aspect of this album that I really enjoyed is the distinctive way of storytelling. He includes a non-singing voice-over on multiple songs, both in his own voice and even featuring a special guest, Dakota Johnson. It’s clear how much his fans are loving it, with the album nearing 100 million streams on Spotify.
However, this album is a complete 180 from Pillsbury’s earlier years.
Role Model, a rapper? You got that right. Before finding his signature sound, Pillsbury was experimenting with rap and releasing music online. After releasing his debut EP “Arizona in the Summer” in 2017, Pillsbury caught the attention of Mac Miller, who invited him to Los Angeles to work together. By 2018, he signed with Interscope Records, beginning a new chapter in his career.
From there, Pillsbury started moving towards the sound that he is known for today. Not to influence anyone’s opinion… but “Kansas Anymore (The Longest Goodbye)” might be one of my favorite albums of all time. You can hear him developing his own sound throughout it, especially in the deluxe version.
This album reflects on the positive and negative aspects of ending a relationship and all of the complicated emotions that come along with it. Similar to “Chuck Timely & the Hourglass,” you can see Pillsbury’s unique talent of making hard emotions digestible and catchy. My personal favorites include “Writing’s on the Wall,” “So Far Gone (ft. Lizzy McAlpine),” “Deeply Still in Love,” “Compromise,” and of course the title track, “The Longest Goodbye.” However, if you listen to it in the right mood, I think this could truly be a no-skip album.
Pillsbury was also able to capitalize on “Sally, When the Wine Runs Out” during his previous tour. On the “No Place Like Tour World Tour,” he began a tradition of bringing other celebrities out on stage to be “Sally,” the character referenced in his song. His first “Sally” was Jake Shane in Dallas, with bigger and bigger names following, including Lizzy McAlpine, Robert Irwin, Kate Hudson, Olivia Rodrigo, Charli XCX and many more.
Between Pillsbury’s honest songwriting and his ability to make being sad in your 20s sound fun, he’s built a sound that is completely his own.