[2] In 2018, Roan started working with producer Dan Nigro, eventually releasing the singles "Pink Pony Club" and "Love Me Anyway" in April and May 2020, respectively.

Olivia Horn of Pitchfork called the album "a bold and uproarious introduction, buoyed by sturdy songcraft and steely indifference to good taste", also writing that Roan is "blessed with a powerful and versatile voice".

[19] Otis Robinson of DIY summarized it as "thoughtful, a little unhinged and entirely contradictory, merging the alt-pop seriousness of Lana Del Rey with the untethered preppy charm of Lorde to go full throttle into messy, emotional fun".

[25] Although not an immediate commercial success, The Rise and Fall of a Midwest Princess garnered a cult following in the months after its release and became regarded as a "sleeper hit" by early 2024.

The album's commercial breakthrough was largely influenced by Roan's supporting act on Olivia Rodrigo's Guts World Tour, her performances at music festivals like Coachella and Governors Ball, and the success of her follow-up single, "Good Luck, Babe!".

By June 2024, The Rise and Fall of a Midwest Princess had climbed the charts, peaking at number one in Ireland, New Zealand and the UK, plus within the top five of the US Billboard 200.