[3] His father, Howard Klein, was a pianist and music critic for the New York Times, and his mother was an artist.
When his father took him on a trip to southwest Virginia, Klein began to develop an interest in bluegrass music.
He was a founding member of the DC area bluegrass group Rock Creek with Randy Barrett,[6] then he replaced John Starling as lead singer for The Seldom Scene, staying with them from 1994 until 1996.
In 1992, they formed Chesapeake with Seldom Scene members Mike Auldridge (resonator guitar) and T. Michael Coleman (bass).
[8][9] When Chesapeake split up, Klein took time off from touring to raise his young children, but eventually began to play the occasional show with Gaudreau.