Dan provided the singing voice for George Clooney in the Coen Brothers film O Brother, Where Art Thou? He is a guitarist and vocalist as part of the Bluegrass band Union Station, which he became a member of in 1994. He is a former member of the Lonesome River Band, for which he was also vocalist as well as playing the mandolin.

As well as playing with Alison Krauss & Union Station, Dan is a solo artist in his own right, having released his first album in 2000, as well as being an in-demand session player.