Randy Houser explained to The Boot how this cut about rural pride came to be: "This song starts off with a bluesy kind of lick that I grew up listening to, like a Robert Johnson kind of slide lick," he said. "The idea of the song came from something my daddy used to say when I was kid," Houser continued: "He would tell me to make sure you go out with your boots on, which meant that if the good Lord was to take you out, go out with your boots on … go out kickin'! Go out doin' what you love — just make sure that's what you do in life." "He passed away back in '97, and it inspired me to write this song," he concluded.
The Drake Vaughan and Eric Welch-directed video incorporates footage of a toddler, Drake Dixon, son of songwriter Dillon Dixon, singing along with the song. The clip of little Drake was originally shot by his nanny, Vickie Vaughan, who subsequently put it on MySpace. After the visual became popular online, Houser decided to incorporate it in his video, making it look like Drake was in his car.
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