I was thinking this expression the other day when it seemed that the odds were stacked against me.
I thought, why do I use the words, "can't win for losing"?
What it that actually mean?
Where did saying that come from and how do those words equate to "the odds are stacked against me"?
Which is a more clear-cut expression?
Best Answer
Elephind and Google Books searches dig up examples of the expression going back to the 1920s. The oldest match is from Johnny Dope, "Squints at Sports," in the [Urbana, Illinois] Daily Illini (May 13, 1920):
From Making Paper, volume 9 (1926) [snippet view], which has the expression on page 180:
and again on page 215:
Also, from "Canyon Splits With Warriors at Local Field," in the [Abilene, Texas] McMurry War Whoop (May 5, 1928):
And finally, from "Temple Hard Luck School," in the Breckenridge [Texas] American (December 7, 1928):
This last account suggests that an early sense of the expression was that the person or team that "couldn't win for losing" performed well in every facet of the task except succeeding in it. However, it may be that other early users of the term used it merely to mean that the person or team couldn't get out of its own way and was destined to lose because it simply didn't know how to win.
As other answerers and commenters have noted, "can't win for losing" has lots of companions in phrases that seem to express kindred sentiment—including the one featured in 1967 Sam and Dave song "I Can't Stand Up for Falling Down", memorably covered in 1980 by Elvis Costello.