I can’t win for losing

What’s the meaning of the phrase ‘I can’t win for losing’?

The odds are stacked against me. (Or no matter how much I try, I never succeed.)

What’s the origin of the phrase ‘I can’t win for losing’?

The saying gradually crept more into use in the 1960s and 70s, and then again in the 1980s, before reaching a peak in the late 80s and early 90s.

Another early written use of the phrase dates back to 1955, in a journal titled National Association of Postal Supervisor, while he expression also appears in the Library of Congress Catalog of Copyright Entries: Third Series, dating back to 1956.

An alternative phrase with a similar meaning is ‘If it wasn’t for bad luck, I’d have no luck at all.’ It can also be interpreted as ‘I just can’t seem to win,’ or ‘It seems like I can’t succeed, and the evidence is in the trying but losing.’ Or more generally, as having a run of bad luck. It’s also appropriate to use when things keep cropping up that spoil your plans.

What are some notable uses of the phrase ‘I can’t win for losing’?

To date, there have been at least three songs titled either ‘I can’t win for losing’ or ‘can’t win for losing’. There was one by T.G, Sheppard released in 1981, one by Don Williams the following year, and more recently one by Mistah F.A.B. in 2016.

The phrase ‘can’t win for losing’ also crops up in the book ‘Tell Me How Long the Train’s Been Gone’ published in 1968. It’s used to describe the relentless challenges that present themselves to the protagonist African American Leo Proudhammer.

Cari Mayhew - Author at Phrase Finder

Cari Mayhew

Lifelong learner, phrase fanatic, and lover of literature across multiple genres. Cari Mayhew has a passion for expression, and a keen curiosity for how phrases begin and how their use transforms over time. She is often found looking for the ideal idiom to convey her thoughts and musings.