Jesse Cobb

Trevor has been a Jesse Cobb fan since 2008. This two-part conversation was recorded right after IBMA 2025, Jesse's first World of Bluegrass since 2008.

Tunes by the wood stove

Jesse grew up on an 80-acre subsistence farm near Dairyland, Wisconsin. For much of his early childhood the house had no power and no TV. The family kept chickens and a milk cow and made maple syrup. At night the entertainment was a book read aloud, or music.

His father played guitar and banjo. His oldest brother, Jed, took up clawhammer banjo, and his brother Shad took up fiddle. Jesse started on guitar, until an older brother claimed it. The only instrument left lying around was a mandolin.

"I think my dad showed me three chords, and then I just started banging along with fiddle tunes. And I'd eventually just pick out the melody."

Later, when the house had power, the brothers borrowed records from the library in Duluth and Superior, slowed them to half speed and learned them by ear. There was no one nearby who played bluegrass. The Grand Ole Opry on the radio filled the gap.

The Cobb Brothers

As kids the brothers played festivals around Michigan, Minnesota, Wisconsin and Ohio as the Cobb Brothers. They made three recordings for Vetco Records in Cincinnati when Jesse was about 12 or 13. He still has the cassettes. Jon Weisberger, a past guest on this show, has long pushed for them to be reissued.

When Jed turned 18 and left the band, the younger brothers followed him into the logging woods. Jesse spent the next years working with his hands: logging, busking on the West Coast with his brothers, helping a family friend train sled dogs in Michigan's Upper Peninsula, and three and a half years repairing railroad bridges from Florida to Oregon. In 1999 he and Jed quit their jobs and drove a two-wheel-drive Ford pickup to Alaska in five days.

He barely touched the mandolin in those years. By his mid-twenties he was set on joining the military. His father and brothers talked him into giving music one more try instead.

First week in Nashville

Jesse moved to Nashville around 2000, where Shad was already part of the scene. At his first jam, Mac Wiseman was holding court and Del McCoury was in the room. A guitar player at that jam asked him to join a two-week tour of Canada. He had a gig in his first week.

He had some catching up to do. Traditional bluegrass was never his first love.

"I was a New Grass Revival guy. That was my whole thing. Sam Bush."

One connection led to the next. He played for a couple of years with Ronnie Bowman, where he got to know Andy Hall and Jeremy Garrett.

The Stringdusters years

Jesse was the founding mandolin player in the Infamous Stringdusters. The band showcased at IBMA in Nashville in 2005 or 2006, as he remembers it, with a five-song EP and every showcase slot they could find. They left with offers from labels and booking agents. In 2007 their debut, Fork in the Road, came out on Sugar Hill, and the band won three IBMA awards that fall, including Emerging Artist of the Year.

He played with the band until 2011. At IBMA 2025 in Chattanooga, he jammed with some of his old bandmates for the first time in years.

Solitude, then Another Road

After a move to Welland, Ontario, Jesse fell in with Mark Lalama, a Toronto piano player and producer with a home studio. He started sitting in on Mark's local gigs, mandolin next to electric piano and bass. When Jesse said he wanted to make a record, Mark asked him why. Then Mark answered for him: you make an album because you have to.

"It's in you, and you've gotta make it."

Solitude came out of three improvised, mostly live sessions. The title fit. There were maybe two other mandolin players in town. Another Road followed in 2016, recorded in four days with Ontario session players who did not play bluegrass. The songs took a left turn, and Jesse picked up an electric guitar on some of them.

The Unfaithful Servants

Back in Victoria, Jesse went to a local musicians' jam at the Duke Saloon. On a break, a stranger sat down beside him.

"Hey, you look like you could use a friend."

That was Dylan Stone, a songwriter deep in the Victoria scene. They started playing together, and Dylan hired Jesse for a session on his songs. Dylan called the record Dylan Stone and the Unfaithful Servants, a band name he had long wanted, taken from a song by The Band. The group grew from there. Their self-titled debut earned a Canadian Folk Music Awards nomination for New Group of the Year.

The pandemic stopped their momentum. The band came back with Quin Etheridge-Pedden on fiddle and Mark Johnson on bass. Their second album, Fallen Angel, produced by Adrian Dolan, came out October 17, 2025. The band made its U.S. debut as an official showcase act at IBMA in Chattanooga, then toured Canada with Shari Ulrich.

Coming back to IBMA after so long, Jesse found the same welcome he remembered.

"It's just like this big family. No matter how outside you are of the family, you're still welcomed back in."