Songfacts®:

• This Jesse Frasure, Shane McAnally and Josh Osborne penned cut delves into the American dream. Chesney sings about the dangers of putting all our hope in our aspirations, as they often lead to more misery.
  
  "This song is very unique for me," said Chesney. "I've been guilty of letting dreams be my master. I think the idea of me singing this song is me finally letting that go in my life and trying to live in the moment as much as I possibly can."
• The video features a college professor, played by Scrubs actor John McGinley, who asks his students to think about who they are and what makes them happy. He goes on to challenge them to look beyond the "rich and miserable" belief fed to them throughout their lives and figure out what they could give to the world.
  
  Chesney filmed the clip despite the track not being released as a single. "I think there's so much more to what goes on a record than radio can play and some songs need to be heard," he explained.
  
  "For 'Rich and Miserable,' it felt like it was addressing so many of the things we're sold and told - about what makes us happy, or we're supposed to want, or are expected to do," Chesney continued. "I didn't want that message getting lost, so we decided to skip a video on some of the singles and do this instead."