West Michigan’s The Bootstrap Boys take vintage country to a No. 1 ranking in 2024

With their distinctive approach to rootsy, retro country music, The Bootstrap Boys have bucked a lot of trends and conquered a lot of musical mountains along the way.

West Michigan’s The Bootstrap Boys take vintage country to a No. 1 ranking in 2024
The Bootstrap Boys [Joshua Tufts/LocalSpins]

With their distinctive approach to rootsy, retro country music, The Bootstrap Boys have bucked a lot of trends and conquered a lot of musical mountains along the way.

The Grand Rapids band has toured the land, won WYCE-FM Jammie Awards (including one for 2023’s Band of the Year), continued to release new tracks and cultivated an ultra-devoted fan base for their candid, gritty music and entertaining stage presence.

So it shouldn’t be a surprise that The Bootstrap Boys emerged as the No. 1 Michigan Artist of 2024 at WYCE (88.1 FM), reflecting the Mitten State band whose tracks earned the most airplay over the past year on the Grand Rapids radio station which showcases more local and regional music than any other station in the state.

The Bootstrap Boys perform in Kalamazoo. [Derek Ketchum/LocalSpins]

“It’s been a great year, starting with winning the big Jammies Award for Artist of the Year as well as Americana album of the year. We are still elated and beside ourselves,” said frontman Jake Stilson, aka Big Jake Bootstrap.

“We then cast our net even wider and had a great May tour around the mid-south and northeast, driving through the Appalachian mountains, making new fans and friends from cool little towns like Shelbyville, Ky., to bigger college towns like Chapel Hill, N.C.”

Stilson credits the band’s steadfast fans for supporting — and requesting — their music.

“Kind and loving, generous and honest, everyday salt-of-the-earth fans like ours are hard-earned. You search for these diehards, and mine those gems and keep them close,” he said. “I hope they come back knowing they’re gonna get some new stories to go home with and to watch a band pour their hearts out on the stage for the love of music.”

The Bootstrap Boys — who released an EP and several singles/covers in 2024 after releasing their award-winning, “Hungry & Sober” album in 2023 — came in ahead of several other popular Michigan artists on the year-end list at WYCE, including Kalamazoo hip hop cellist Jordan Hamilton, neosoul’s Earth Radio and bluegrass superstar Billy Strings.

The diverse list of Michigan artists whose music resonated the most with radio programmers and listeners also included Pablo Eskobear, Candid Antics, May Erlewine, Cal in Red, Pretoria and the nationally acclaimed The War and Treaty. 

After experiencing special nights and finding “love and magic” on the road in 2024, The Bootstrap Boys will close out the year with a performance on New Year’s Eve as part of Kalamazoo’s New Year’s Fest, joining more than 20 other acts playing several different downtown venues.

— Find more Michigan music features and concert listings at LocalSpins.com.