"Long Line of Losers" is a song recorded by American country music duo Montgomery Gentry. It is the fourth single released from their sixth studio album, Back When I Knew It All. Kevin Fowler who co-wrote this song also recorded this song on his 2007 album Bring It On, also released his version as a single, but it failed to chart. Montgomery Gentry's version debuted at #48 in June 2009, was a Top 30 hit for the duo with a peak of #23 in October 2009.
Dan Milliken of Country Universe gave the song a B+ rating, and said this in his review of the song that it was "their most country-sounding single in some time." Milliken also said that it showed influences from Alabama and Hank Williams, Jr., and that its songwriting "breathe[d] new life" into a common theme of showing pride in a broken family. Bobby Peacock of Roughstock also gave a positive review, calling it "a good example of Montgomery Gentry's musical evolution" and saying that it continued in the "sense of maturity" present in such singles as "Back When I Knew It All" and "Roll with Me."
"Long Line of Losers" debuted at #48 on the U.S. BillboardHot Country Songs chart in June 2009. It peaked at #23 on the country charts in mid-October 2009, becoming their first single to miss the top 20 since "You Do Your Thing" reached #22 in 2004.