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Fred Eaglesmith's songwriting uses techniques of short story writing, including unreliable narrators, surprise endings, and plot twists. In 2016, Eaglesmith tours extensively with his band. Eaglesmith, one of nine children, was raised by a farming family near Guelph in rural Southern Ontario. He began playing the guitar at age 12. As a teenager Eaglesmith hopped a freight train to Western Canada and began writing songs and performing.
Eaglesmith founded a band known as the Smokin' Losers. He later formed a group called known as both the Flying Squirrels and the Flathead Noodlers, switching the name to represent different styles of music. The Flathead Noodlers play bluegrass, while the Flying Squirrels play more folk and rock. His first self-titled album was released in 1980.
A typical Fred Eaglesmith show includes his music set between several lengthy between-song comic monologues by Eaglesmith. Topics in the past have included stories about crossing the U.S.–Canada border, Newfoundlanders, and some friends from an Indian reserve. His fans are known as "Fredheads", a nod to deadheads, who followed the Grateful Dead. He is known to tour extensively throughout Canada and the U.S. When Eaglesmith appears in solo performances, he bills himself as Fred J. Eaglesmith. In addition to his own albums, he frequently collaborated with the late Willie P. Bennett, a former member of Eaglesmith's band, who stepped down after a heart attack in early 2007. Eaglesmith publishes his own records. In 2010, Eaglesmith was featured on the Late Show with David Letterman as the musical guest. Since 2012, performances have been billed as the Fred Eaglesmith Travelling Steam Show and include opening songs performed by Bill Poss, the Ginn Sisters, and his wife Tif Ginn.