High Quality Content by WIKIPEDIA articles! Montgomery Gentry is an American country music duo composed of Eddie Montgomery and Troy Gentry. Its discography comprises six studio albums, three compilation albums, one extended play, and twenty-six singles. The duo made its debut in 1999 with the single "Hillbilly Shoes," which went to number 13 on the Hot Country Songs charts, but did not reach Number One until mid-2004, with "If You Ever Stop Loving Me." The duo has sent four more singles to Number One for a total of five: "Something to Be Proud Of" (2005), "Lucky Man" (2007), "Back When I Knew It All" and "Roll with Me" (both 2008). Besides these, Montgomery Gentry has reached Top Ten with ten additional singles. All fifteen of these songs have also crossed over to the Billboard Hot 100, where the duo`s highest peak is "If You Ever Stop Loving Me" at number 30.