This honky-tonk heartbreaker finds Mark Wystrach singing of a woman who has given up trying to change her lover, whose life is devoted to the music. She said, "I guess there ain't no right way For you to say goodbye again You been looking at the highway Where your heart has always been" The woman's farewell to her wandering minstrel beau is one of resignation. However, she recognizes her man's need to pursue what he's good at.
The title is a play-on-words twist on the usual definition of a playboy: an irresponsible man. Wystrach explained to Billboard: "The song's about actually having that support and having somebody, that significant other that might be frustrated with the realities of a traveling band, but looks at each one of us, our respective partners, and says, 'Well you're good, you're great. You gotta go out there and do this and I understand it.'"
Midland's Jess Carson, Cameron Duddy and Mark Wystrach co-wrote the autobiographical tune with Shane McAnally and Josh Osborne. Wystrach explained: "That's directly culled from real-life experiences. You're talking about our name on the marquee sign. Pulling up to The Houston, being exhausted."
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