McCutcheon is first and foremost an instrumentalist. Like thousands of others in the '60s, McCutcheon, a Wisconsin native, taught himself how to play a mail-order guitar and joined the local folk scene. His interest became more serious, however, when he sought to find the roots of this music. McCutcheon headed for Appalachia and learned from some of the legendary greats of traditional folk music. Along the way, he became adept at a multitude of instruments, including fiddle, banjo, guitar, autoharp, jaw harp, and especially the hammered dulcimer. McCutcheon is considered one of the undisputed masters on the hammered dulcimer and adapts much of his music around the instrument.

As a new father, McCutcheon found most children's music "unmusical and condescending." In 1983, he sought to remedy the situation with his first release for Rounder, Howjadoo. McCutcheon thought that Howjadoo would be the only children's record he would make. But the critical acclaim for Howjadoo was such that several other children's albums followed. McCutcheon's 1988 release Mail Myself to You featured several songs by classic folk composers such as Woody Guthrie and Malvina Reynolds. In the hands of McCutcheon, these old songs gained new luster. Family Garden followed in 1993, with several original tunes including the evocative "Baseball on the Block." McCutcheon also turned to producing and, on the Rounder label, encouraged other folk and world musicians to address children as an audience. He created the 1992 Rounder release Rainbow Sign to benefit the Grassroots Leadership, a community-building non-profit organization in the South. In 1997, McCutcheon produced two storytelling compilations to again benefit the Grassroots Leadership.

McCutcheon started a new series of children's albums in 1995 with the release of Summersongs. The album featured several tunes about the daily life of kids, with songs like "Power Mower" and "Haircut." Later that same year, Rounder released the second album in the series, Wintersongs. Again, the recording featured several cuts about the common joys of winter, including "Soup" and "Hot Chocolate." The most popular song on the album, however, was the easily imagined "Tommy Don't Lick That Pipe," written by McCutcheon and his longtime friend Si Kahn. Wintersongs was nominated for a Grammy in 1996. Storied Ground followed three years later. The time between albums reinvigorated the singer/songwriter, and in 2001 he followed it up with Supper's on the Table... Filled with more socially conscious lyrics, the album had the look and feel of an old-time folk record. The next year, a more contemporary-minded McCutcheon put out The Greatest Story Never Told on Red House Records.

It was four years before McCutcheon released another full-length album. 2006's Mightier Than the Sword was a literary effort, featuring collaborations with contemporary poets and fiction writers such as Wendell Berry, Rita Dove, and Barbara Kingsolver. McCutcheon also came out with a children's audio book that year called Christmas in the Trenches, which went on to garner a Grammy nomination in the children's spoken word category. Hail to the Chief! and Stand Up!: Broadsides for Our Times came out the following year. ~ P.J. Swift