This debut album from Brittany Howard is named for Howard's elder sister who died from retinoblastoma in 1998, aged just 13. The singer told Mojo magazine: "Spiritually that's someone I feel, even though they're not here. Most of my memories of my sister are of her teaching me something. Getting to talk about her, and how meaningful her presence in my life was, and it's not being a thing of, like, sadness, it felt like the right thing to do. She was one of those people, she never complained about anything. When she lost her vision, she still created art. That puts everything into perspective. I like sharing who she was with people."
Cheryl welcomed Brittany Howard into the KEXP studio for a live performance of songs from "Jaime" in 2019.: https://youtu.be/L3aOCIwtYbo
Brittany Howard said regarding the song's meaning: "'History Repeats' is as much a personal song as it is a song about us as a human species. Our times of success may propel us forward, but our repeating failures hold us back from evolving into harmony."