Songfacts®:

• 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."
• One of the lyrics hit especially close to home for the Midland trio.
  
  Out here you get used to losing your friends, your lovers, and your mind
  
  Wystrach told Billboard: "Sometimes it does feel like that, but it's about that joyous moment that refills the coffers: Jumping on the stage with your friends and making music that's very compelling that the fans are eating it up. They love it and it's cool when you get to meet the fans."