Songfacts®:

• Sam Williams, the grandson of the great Hank Williams, recorded this reflective and moving track for his debut album, Glasshouse Children. It finds him contemplating how material wealth can't make you happy, as you still can't buy love and peace of mind. "I wanted to bring a new outlook to the thought that money can't buy happiness," Williams told Apple Music. "I believe if we could attain happiness through transaction, then we would try to, but it still wouldn't be enough."
• Williams wrote the song with songwriter Mary Gauthier a few years before recording it for Glasshouse Children. He'd always wished for Dolly Parton to accompany him on it, so he sent her the track along with a two-page letter. Dolly replied, saying she loved the tune and would be honored to sing on it. Asked by Billboard what he put in a letter that convinced the country legend to sing with him, Williams replied:
  
  "Real emotions, real words. I spoke of my life, my childhood, what 'Happy All the Time' means to me, and how validating it would be for me for her to sing with me. I think she really felt connected to the message of the song and just me in particular, for some reason."
• Once Williams had a duet with the country legend on his hands, it changed everything for him, as now he needed to sharpen up his songwriting muscles. He told Apple Music: "I knew I was going to have to really push myself if I wanted to write an album powerful enough to stand alongside that."
• Sean McConnell (Brett Young's "Mercy," Rascal Flatts' "Come Wake Me Up") produced the song with Bobby Holland.
• Williams performed the song along with "Glasshouse Children" and his grandfather's classic hit "I'm So Lonesome I Could Cry" during his Grand Ole Opry debut on August 15, 2021.