“High Sierra” was written by Harley Allen, the singer and songwriter born in Dayton, Ohio, in 1956, the son of the bluegrass performer Red Allen. Eddie and Martha Adcock recorded it under the title “Wrong About You, Right About Me” on their 1980 CMH album Love Games, and Eddie Adcock cut it again for Talk to Your Heart (CMH, January 1995). The bluegrass band Chesapeake — Moondi Klein, Jimmy Gaudreau, Mike Auldridge and T. Michael Coleman — recorded it for their Sugar Hill album Rising Tide in 1994.
The lyric looks back at a failed love. The singer says he has been higher than the High Sierra and lower than Death Valley, that he has been mostly wrong — wrong about her, right about himself — and that passion has turned to pain, yet the sun shines most of the time and he believes he will come back.
Dolly Parton, Emmylou Harris and Linda Ronstadt recorded it in 1994 for what became Trio II. Ronstadt used a mix without Parton on her 1995 album Feels Like Home, and Trio II itself came out on 9 February 1999 on Asylum, with “High Sierra” issued first as its single. On that track Mark Casstevens and Carl Jackson play acoustic guitar, David Grisman mandolin, Alison Krauss fiddle and Roy Huskey Jr. double bass.