The Bootstrap Boys will take you back to Nashville in 1972. Who knew we could have the Deep South this far north?
— Quinn Matthews, WYCE/Experience Grand Rapids


The Bootstrap Boys are singlehandedly reviving country music in West Michigan both in attitude as well as song. The band’s ability to tell stories indicative of a life lived on the razor’s edge is only eclipsed by the ease with which they connect to their audiences.
— Luke Sass, Promotional Manager, Founders Brewing Company


The Bootstrap Boys are a Grand Rapids, Michigan-based country band, formed in the spring of 2015 under blue suede skies in the long shadow of a grizzled old oak tree. Led by frontman Jake Stilson, a long-standing edifice in West Michigan's surprisingly fertile music scene, The Bootstrap Boys  initially emerged onto the scene as a tongue-in-cheek outlaw country outfit as an outlet for Stilson's more satirical artistic offerings. However, in a few short years' time, the band has come to define country music in West Michigan, and exhibits the Midwest's potential to not only contribute to, but shape and reshape the genre's bright future.

With 80+ shows and a few handfuls of festival plays in 2018, all while each member works a full time job, juggling family, friends and responsibilities, the natural progression of artistic growth led them to an eventual conclusion: with so much time spent on the project and with Stilson at the helm, it was time for The Bootstrap Boys to up the ante.

Stilson, brutish but approachable, is equal parts grizzly and teddy bear. His greyish eyes portray a distant kindness, yet the wrinkles under them indicate wisdom, a lifetime of hard work, of grit, of the long road behind and the long road ahead. The scars on his hands tell tales far beyond the pen, the piano or the guitar - they ring of life, love and loss, subjects in which The Bootstrap Boys have collectively embraced as they mature as artists and storytellers.

After several months of nose to the grindstone at Rick Johnson's Cold War Studios, expanding the sound to include more banjo, additional auxiliary percussion as well nubile themology and strikingly beautiful four-part harmonies, The Bootstrap Boys are set to release their sophomore studio Album, Between The Hat & The Boots. They’ve handcrafted ten brand new tunes with love for all.

The Bootstrap Boys can readily be seen on stages and haylofts around Michigan, the Midwest and beyond.

Grand Rapids’ Bootstrap Boys...ooze the sort of throwback, outlaw-hued country music that’s really resonated with West Michigan audiences since the group released its first EP, “Country Songs for Sale,” back in 2015
— John Sinkevics, Local Spins

We’re honored to have shared the stage with:

Nora Jane Struthers & The Party Line Shooter Jennings Angela Perley Lost Dog Street Band Nathan Kalish & Many More to Come

It was a scene right out of a really good nightmare. Classic country telecaster twang literally called out to the crowds of campers settling in for the night. I moved like a zombie in the direction of the Feedbag Cafe, where the flashing neon and loud drunken banter tried to but could not conceal the excellence of Big Jake’s voice and the band’s driving, dangerous and infectious rhythm. It was an odd time and place to be treated to such an outstanding and fleeting gift of music.
— Jay Gavan, The Corn Fed Girls, Local Spins, 2018


Li'l Mama Bootstrap, Management - - (616)560-3554 -