Eaglesmith's band is known both as The Flying Squirrels or 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. An early incarnation of the band was known as The Smokin' Losers. 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 does solo appearances 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. He appeared in a 2001 television movie titled The Gift. Eaglesmith publishes his own records.
In 2010, Eaglesmith was featured on The Late Show with David Letterman as the musical guest. He performed "Careless" from the album Cha Cha Cha.
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