The song was penned back in 2011 when Cole Swindell and his pal Josh Martin were a pair of struggling songwriters. The pair wrote together as part of a small group of friends and co-writers that also included Adam Sanders. Martin threw out 'Ain't Worth the Whiskey,' a title he'd been carrying around for a while during one particular writing appointment. "Adam threw out a few more titles, and I started spitting out more titles, and Cole said, 'What are we doing - why the hell ain't we writing 'Ain't Worth the Whiskey'?" Martin recalled to Taste of Country, laughing. "So we stopped in our tracks, and I said, 'I agree.' And Adam said, 'Yeah, I like that, too. That's probably the best hook that's gonna come out of the room tonight.'"
It was Swindell himself who hit upon the song's unique angle. "I didn't really want it to be a non-drinking song," Martin said. "I didn't want it to be about, we're gonna quit drinking because this girl has broken our heart. And then Cole said, 'Let's do the opposite - we'll drink to this, and we'll drink to that, but she's not worth the whiskey.'"
The song got pitched around Nashville, and both Montgomery Gentry and Thompson Square put it on hold before Swindell eventually recorded it for his 2014 debut studio album.