Klein is a winner of many prestigious awards, including the 2008 Diamond Award for Best Individual Artist from the Peninsula Arts Council, the Silver Lei Award from the 2009 Honolulu Film Awards (for the World Premiere of Giancarlo Aquilanti’s "La Poverta"), the 2000 ASCAP Award for Programming of American Music on Foreign Tour, the 2001 Julie Billiart Award from the College of Notre Dame for Outstanding Community Service, a 1996 award for the year’s best television performance program in the Western States (for the one-hour PBS program about him and the Peninsula Symphony, called "Music Making: A Joyful Vocation") as well as the Hillbarn Theatre's 1993 BRAVO! Award for his contribution to the Bay Area’s cultural life.