"A Born Loser" is a 1966 country and western single by Don Gibson, a country artist who made a career out of singing dejected songs. Despite the sad title, this song is a swinging, almost chanted number where Gibson speaks, in a rich baritone, about his string of romantic failures.

When I first heard Don Gibson, a few weeks ago, with "So How Come", I was listening as an innocent, and I was impressed. I said that the song had a combination of crooning, sweet and syrupy singing, with a little bit of swinging and rawness. And that is how I feel about this song. The tale of romantic rejection seems sad, but it is told in an Aw Shucks way that makes it seem relatable, instead of angsty. But whereas that first song came out in 1962, when popular music was at a nadir and a simple, but heartfelt song was quite acceptable, this came out after folk and rock music had changed the musical landscape, and where even country music was changing to more personal stories. What seemed heartfelt and sympathetic in 1962 seemed like a gimmick in 1966. I certainly like Don Gibson, and I like this song, but it showed how country music's standard topics and presentations were getting old by 1966.