Longfellow resident Jeremy Messersmith sang the chorus of his new song “Boomers” to a crowd at the Union Depot for the Train Days Music Fest. “Just relax, sip your wine, stay alive, and wait for all the boomers to die,” the lyrics went.
“A bunch of people laughed, a bunch of people laughed and gave me the finger, and then some people just gave me the finger. All of those are totally valid,” said Messersmith.
This isn’t just at big shows. Messersmith performs over 40 backyard potlucks each summer. Mid-set, he answers attendee-sourced paper slips from what he dubs The Jar of
Inappropriate Questions. “I’m still me, just turned up a little bit, just a little smarter, or a little wittier, or whatever,” Messersmith said.
A Twin Cities cult favorite, Messersmith released a new album on April 1 called “Fox/Coyote.” For the album, he wanted to explore “subverting expectations in a song. It’s one of the most fun things you can do when you reward people who are listening with a surprise and a shock.”
But it hasn’t always been like this. Messersmith has walked a long and imperfect path to self-confidence.
Confidence wasn’t easy to come by
Messersmith grew up as a homeschooled kid in Tri-Cities, Washington, with a deeply religious family. The first time that he remembers performing was a kindergarten Christmas pageant. “I don’t remember the song at all, but I do remember that I was a sheep, and I sang a song,” he recalled,
Confidence wasn’t easy to come by. He played trumpet in a local school’s band. “I just remember all the saliva leaving my mouth entirely,” he said. “I was really, really terrified playing in the school cafeteria.”
That trumpet-playing kid eventually grew up and moved to Minneapolis to find himself. He wandered around different coffee shops and bars, performing unwanted gigs that his girlfriend booked for him and forced him to play.
‘DAN, SEND ME NOTES ON THIS’
One night at Acadia, Semisonic frontman Dan Wilson showed up. Messersmith was nervous. “I’d learned to play guitar from listening to Semisonic albums.”
After the show, he was distraught. He cried in the car, berating himself about how bad the gig was.
But once Messersmith got up to his Loring Park apartment, he found a message from Wilson on his answering machine.
“Hey, I really, I caught your gig at the Acadia. I really liked it. Would you like to get together and have coffee sometime? If you’d like to, my number is 612, beep. I had run out of tape.” Thankfully, Wilson called back and gave him his full number.
Wilson became a mentor to Messersmith, advising heavily on Messersmith’s debut album,
“The Alcatraz Kid,” and producing “The Silver City.”
“I still will send songs to Dan and be like, ‘Dan, send me some notes on this,’” Messersmith said.
A WAY TO TOUR THAT DIDN’T SUCK
After touring for “The Reluctant Graveyard” in 2011, Messersmith realized that touring sucked. He said he was lonely and bored on tours all across America.
“I just made a list of all the things that kind of suck about it. Then I brainstormed with my bandmates. Maybe there was a way to tour that didn’t suck,” Messersmith said.
They finally settled on backyard potluck concerts. He remembers thinking, “What if it was just, like, at somebody’s house? What if it were a potluck? That way, I’m not eating Taco Bell three times a day.”
The first home show was at a home along the Mississippi in St. Paul for a Friends of the Mississippi fundraiser.
“They paid me $2,000 to come play in their backyard. And I was like, ‘What am I even gonna do with that much money?’” Messersmith recalled.
After the show, he thought, “This is good. I think I could do this for the rest of my life, actually.” Thus began the home shows with something he called The Supper Club.
What began as a way to eat better food and drive fewer miles became something that helped him grow as a musical artist. “It just feels a lot more organic and anarchist, in a way,” Messersmith said.
This organic model gradually made Messersmith more confident on stage, leading his drummer to remark, “Dude, your banter got really good – like, you talking was not a thing people are cringing through anymore.”
At times, these home shows are also his harshest critic. “It’s painfully obvious if your songs are not working. People just drift off, or pull out their phones or whatever,” Messersmith said.
That said, confidence is never perfect, and performance always comes with pitfalls.
“My voice cracks, or the power goes out, or a tree branch falls two feet from me,”
Messersmith said. Sometimes at night, he wakes up at 2 a.m., thinking, “What if I put together a slideshow of the most cringeworthy performance moments of your life? We just speed around those. Wouldn’t that feel great?”
But over time, Messersmith has grown to incorporate crowds into his sound. During the COVID-19 pandemic, he felt very isolated.
“I was recently divorced, all my gigs were canceled, and I wasn’t seeing many people. I went off the rails – at least, as far as songwriting went,” he said. ”Without any social context, my songs just got really weird because I was just writing to amuse myself.”
As the pandemic subsided and he began to do home shows again, he found that people loved the songs: “Turns out everyone else was just as deranged and unhinged as I was.”
He tried to record these pandemic-era songs in the studio, but found that they fell flat. He realized, “It’s missing the audience. The audience is actually an instrument. Without it, it just feels like a sitcom without the laugh tracks.”
This epiphany led him to record a 2024 live show at Bryant Lake Bowl – in a bowling alley. In the album’s description, it states, “Enjoy the clinking glassware and savor the occasional misplaced note. We could’ve fixed them, but we didn’t.”
F*CK THIS
Messersmith’s confidence onstage has transformed into community leadership; he has become increasingly political. In 2010, he opened for President Barack Obama, and later he opened for Vice President Joe Biden at a separate event. On his new album “Fox/Coyote,” he directly addresses political issues in his songwriting for the first two tracks, “Billionaires” and “Boomers.”
Messersmith and collaborator cellist Dan Lawonn were involved in anti-ICE protests this winter, including some at the Whipple Federal Building. Messersmith also wrote a song called “F*ck This,” condemning ICE involvement in Minnesota.
Jen Ohm and Mark Ohm have hosted Messersmith and Lawonn several times over the last four years for home shows, but this winter, they asked him to do something different: to perform a concert in their living room six days after the murder of Alex Pretti. The answer was a resounding yes. At first, Jen Ohm was apprehensive and wondered, “Can you even bring people together?”
The Ohms crammed over 30 people into their small Hiawatha living room and kitchen on folding chairs. As Messersmith stood up with his ukulele, the tension was palpable. And then he started with his recently released “F*ck This” song featuring lyrics like “F*ck those, ICEholes, go f*ck yourselves and then eat sh*t.” The living room erupted as 30-plus belted the song alongside Messersmith and Lawonn.
The duo performed a 70-minute set. “It was very fun and very cathartic to have a normal place where normal people were having a normal, fun time,” M. Ohm said.
“We needed to sing that song out loud,” J. Ohm said. “Everybody needed to be together and a little bit looser and know it’s okay to be together in this really stressful time, and make music together.”
As the set concluded, Messersmith paused and asked, “What else do you want to hear?” to which an audience member yelled for “F*ck This” “so, we did it again with more gusto,” J. Ohm said.
Ben Aviles will be a senior at Blake School in fall 2026. He is editor-in-chief of The Spectrum, Blake’s school newspaper.
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