The album was recorded during their Ryman Auditorium residency in Nashville, Tennessee spanning over three nights. They confessed on The Bobby Bones Show that most of the recordings were taken from one night, but they did swap out a few of the songs from the other shows if they thought it sounded bad. This was the duo's first ever time headlining The Ryman and they credit the live record sounding so good to the crowds. They said their fans were singing all the lyrics perfectly to each song, and if it weren't for them, the record would have sounded staged. Brothers Osborne also noted that it was weird hearing their tones sound different live, but with a live record you have to "let things go, let it be, and not have perfection."
Before they were Brothers Osborne, they were actually named after a local liquor store in their hometown of Deale, Maryland. They named themselves "Captain Kid," but after a band overseas starting making headlines with this name, they decided to change theres to reflect the fact that they were brothers. The duo often gets mistaken by news outlets as Florida Georgia Line and Old Dominion, which they joked doesn't make any sense because there are only two of them and five members of Old Dominion.
John was asked what TV family most resembles their family, and he said without hesitation Rosanne. He shared that they're blue collar, working class, and things can fall apart at any moment. He laughed sharing that he and TJ have the least personality out of their family. With working class as their backbone, it makes sense that his favorite advice from an artist was Paul Franklin who said,
"Work hard and be nice to people and everything will unfold."