I'll Sleep When I'm Dead

It could be Clive Owen's grizzled face staring down from the poster for the movie I'll Sleep When I'm Dead, or Warren Zevon's grizzled face staring up from the cover of the anthology album of the same name, but I have always associated the phrase "I'll sleep when I'm dead" with a sort of poseur aggressiveness that was undoubtedly honed to precision in some PR lab, similar to Nike's "Just Do It" or any of a dozen similar phrases and vibes you find in, say, beer commercials. 

But I have a new theory.

As someone who is dying, but not dead, and who is finding it nearly impossible to sleep through the night, it's possible "I'll sleep when I'm dead" is intended as more of a pathetic acknowledgement that there's at least one actual benefit to dying: you'll finally get a decent night's sleep.

On second thought, it's probably the PR-honed aggressiveness. 

But I can't say I decent's night sleep doesn't sound really nice about now.