The Bootstrap Boys ride on to launch concert series, record ‘massive’ new project

West Michigan’s The Bootstrap Boys will launch a new season of Michigan musical magic tonight at SpeakEZ Lounge in Grand Rapids.

And frontman Jake “Big Jake Bootstrap” Stilson says, although it’s been a different experience performing since guitarist Nick Alexander passed away suddenly from heart complications, the vintage country and outlaw country band has carried on impressively with help from a bevy of friends and fellow Michigan musicians.

“We have to firstly give thanks to the very healthy and helpful local music scene in West Michigan,” Stilson said.

“We have played with seven different musicians so far this year, that have stepped up to try and fill the void. Yes, it’s sad. Yes, it’s different. It will always be a bit of both going forward. 

“Having great experiences with new players? It doesn’t draw away from the grief, but it does inject a nice dose of ‘sticktuitiveness,’ and I know Nick would not have wanted us to not give up at this stage in the game.”

In that vein, “the one and only Justin Wierenga will be showcasing his pedal steel and six-string prowess” with The Bootstrap Boys when they play the first fall show of the Local Spins Wednesdays series at SpeakEZ Lounge at 7:30 p.m. Sept. 17. 

Stilson previously has said that all of the band members are “now standing on the shoulders of the work that (Alexander) put into this project with us.”

The Bootstrap Boys — who won the WYCE Jammie Award for “artist of the year” two years in a row in 2024 and 2025 — have lots on tap in the coming months as well.

“We have been and are currently working on a massive project, in our hometown studio (Cold War Studios) with fabulous recording engineer Rick Johnson,” Stilson revealed. “We are bringing in all our friends and have even made some new ones in the process. We are adding fiddle, steel, organ, piano, harmonica, etc., and feeling great about all of it.”

Stilson added that the band is “going all out” for this project, “spending the extra time to fill in the blanks, and bring the final product to where we’ve always imagined it could be.”

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The band will also perform:

• Sept. 26: “ArtPrize Halftime Show” at Grand Rapids Sixth Street Park
• Sept. 27: Wealthy Street Block Party
• Nov. 1: “Day of the Dead Benefit for Nicky” at Founders Brewing in Grand Rapids
• Dec. 21: The band’s annual “Winter Solstice Party” at Tip Top Deluxe Bar & Grill

SpeakEZ Lounge, meanwhile, is also kicking off regular Sunday jazz nights hosted by saxophonist Tommy Pancy (a Grand Haven High School alumnus) as well as a full slate of Wednesday and Friday night concerts starring Michigan artists. View the schedule online here. 

— Find more Michigan music news and concert listings at LocalSpins.com. Email John Sinkevics at john@localspins.com.