After a solo career, Royal Reed, a native of El Paso, Texas, met Chris Roberts, a native of New Orleans, Louisiana, in the late 1990s while both were starring in a production of the Broadway musicalThe Civil War, alongside singer Larry Gatlin, in New York City. Gatlin, who had once fronted a trio which also included his two brothers, mentored Reed and Roberts, also suggesting that they should add a third member to complete their vocal-centric group. Initially, they could not find a suitable third member for the trio. Eventually, they befriended Marcus Hummon, with whom they began to write songs. Through Hummon, the two discovered South Carolina native Eddie Bush, who was added to the group in 2005. The three members discovered that they worked well together as a vocal trio, and assumed the name One Flew South. The three all sing lead vocals on their songs. One Flew South's first recording was the song "Friends for Life", which Hummon co-wrote; the trio recorded the song on the soundtrack to the 2006 film The Fox and the Hound 2. After that song was released, the trio began recording demo tapes while seeking a record deal. With Hummon's help, they were signed to a recording contract with Decca Records in 2007, as well as a publishing contract with Sony/ATV Publishing. Their debut album, Last of the Good Guys, was released on May 27, 2008, debuting at No. 67 on the BillboardTop Country Albums charts; most of the songs on it were co-written by the group's three members, along with Hummon and rock songwriter J.D. Souther. Hummon also produced the album, in addition to playing guitar, piano, and mandolin on it. The album's lead-off single, "My Kind of Beautiful", was co-written by Andy Griggs, who previously recorded it on his 2005 album This I Gotta See. It went for radio adds on June 2, and debuted at No. 57 on the BillboardHot Country Songs charts for the chart week of June 21, 2008 where it stayed for one week. For the week of August 16, 2008, the song re-entered the Hot Country Songs charts at No. 56. On June 25, 2019, The New York Times Magazine listed One Flew South among hundreds of artists whose material was reportedly destroyed in the 2008 Universal fire.