Part of the roots music explosion that took place in Southern California during the '80s, the Lonesome Strangers' harmonies evoked great fraternal duos like the Delmore Brothers and Everly Brothers, even though leaders Randy Weeks and Jeff Rymes weren't related at all. Weeks, a transplant from Minnesota, and Rymes, a Colorado native, founded the band in Los Angeles in 1984 (some accounts have it as early as 1982); their initial rhythm section featured bassist Nino Del Pesco and ex-Wall of Voodoo drummer Joe Nanini. Blending their vocal harmonies effortlessly over a blend of vintage country and roots rock, the Lonesome Strangers played around the L.A. club scene and quickly attracted the attention of producer Pete Anderson, who would soon make his name helming Dwight Yoakam's records. Anderson included their "Lonesome Pine" on the 1985 compilation A Town South of Bakersfield, which gave crucial early exposure to Yoakam, Rosie Flores, James Intveld, and other Americana-minded artists from the resurgent Los Angeles/Bakersfield scene. Anderson produced their debut album, also called Lonesome Pine, which was released on the small Wrestler label to positive reviews. Nanini left the band after the album was completed but before it was released, allowing new drummer Mike McLean to appear with the group on the artwork. The Strangers toured behind Yoakam and Dave Alvin, after which Del Pesco departed to form Snakefarm with Barry McBride; he was replaced by Lorne Rall.
Weeks and Rymes lent backup vocals to Yoakam's acclaimed Buenos Noches From a Lonely Room in 1988, and the Lonesome Strangers moved to a larger label in HighTone. They issued their second album, an eponymous effort, in 1989, once again to highly complimentary reviews. However, when Rymes relocated to the East Coast in the early '90s, the band went on hiatus. Rymes' return to Los Angeles several years later quickly brought about a reunion with Weeks, and eventually a new album, 1997's Land of Opportunity. It was released on Anderson's Little Dog imprint and co-produced by him and Dusty Wakeman, who filled the empty bass slot (drummer Jim Christie and keyboardist Skip Edwards also played on the album). Jeff Roberts was later hired as the touring bassist, and the drum chair was filled first by ex-Plowboy Kenny Griffin, then Greg Perry.