Crosby began recording the album two years ago with help from his son James Raymond and co-producer Daniel Garcia. The sessions took place at Jackson Browne's Groove Masters studio in Santa Monica, California as well as at James Raymond's home studio. "We didn't have any money," Crosby explained to Rolling Stone. "None. We could have gone and gotten a deal, but everybody in the music business is very leery about the big companies and what kind of lifespan they might have. Most people are doing it on their own, so that's what we did."

The album includes a guest appearance from Mark Knopfler on album opener "What's Broken." As Crosby explains, "We sent him the song and he just [expletive] killed it. He did me a huge favor and we don't even know each other. He's just brilliant." And jazz great Wynton Marsalis plays trumpet on the track "Holding on to Nothing."