Can’t win for losing refers a popular United States-based colloquialism, used for expressing a series of bad luck and a lack of success.
A good example for a situation, which may invoke the feeling is a Pay to Win videogame, where a user truly “Can’t win for losing” resulting in a lack of Winner Winner Chicken Dinner message, displayed onscreen.
“Can’t win for losing” has been around in the English lexicon since the 1920’s, with the first documented case of the idiom appearing in print being issued in the Daily Illini, mentioned in the “Squints at Sports” bracket, written by Johnny Dope and published on May 13th, 1920.
The colloquialism would appear in several other cases in the years to follow, mostly in books and magazines, however it didn’t see widespread usage until decades later.
“Can’t win for losing” started gaining traction at the end of the 1940’s, when it was featured more frequently in print, as well as verbal uses, appearing on the radio, as well as television series.
By the second half of the century, the idiom appeared in countless sources, including music, such as the Grateful Dead’s “Cumberland Blues” as well as a Teddy Pendergrass song, titled “I Can’t Win for Losing”.
The phrase was first defined on Urban Dictionary on March 5th, 2008.
By the 2010’s, “Can’t win for losing” even appeared on numerous image macro memes on sites like 9GAG and me.me.
- Writingexplained.org – What Does Can’t Win for Losing Mean?