Waylon Jennings, a reluctant figurehead of the 1970s outlaw country movement, publicly rejected the "outlaw country" label as little more than a marketing tool, even while his own material reinforced the very image he disavowed. Despite his objections, his song "Are You Sure Hank Done It This Way" became a defining anthem of the genre and a chart-topping hit, illustrating the tension between an artist's self-perception and the commercial narrative built around him.

The track first appeared on Jennings' 22nd studio album, Dreaming My Dreams, released in June 1975, before coming out as a single that August. It reached number one on the Billboard Hot Country Songs chart and crossed over to number 60 on the Billboard Hot 100. In its lyrics, Jennings questions whether Nashville's slicker "countrypolitan" artists, such as Glen Campbell and Dolly Parton, were true heirs to Hank Williams, contrasting them with grittier "outlaw" peers including Willie Nelson and Kris Kristofferson.