Olson has received a range of recognition for his work as a music historian, including nine Grammy nominations. He holds a Ph.D. in English and Southern studies and has produced and curated a number of documentary albums of Appalachian music, including five boxed sets for Germany’s acclaimed Bear Family Records label (separate sets featuring the complete recordings from the 1927-1928 Bristol Sessions, from the 1928-1929 Johnson City Sessions, from the 1929-1930 Knoxville Sessions, from the 1946-1954 Rich-R-Tone and Folk Star labels, as well as a compilation of Tennessee Ernie Ford’s early recordings); four albums of Appalachian music for Great Smoky Mountains National Park; four albums for Rhino Records (the 50th anniversary edition of a seminal Elektra/Folkways 1960s-era folk music anthology, the 50th anniversary edition of Love's album Forever Changes, and two anthologies of classic recordings by Carly Simon and other Elektra artists); two albums for Craft Recordings (a retrospective collection of Doc Watson’s recordings and a compilation of historical African American music); an album for June Appal Recordings celebrating contemporary hip-hop music from Appalachia; and an album for Rivermont Records collecting the first commercial recordings made in Appalachia, the 1925 Asheville Sessions.