English singer-songwriter Holly Humberstone's professional music career began in 2020, when she independently released her first single, "Deep End". It was included on her first EP, Falling Asleep at the Wheel (2020). She then signed with Polydor, Darkroom and Interscope Records, as well as attaining a publishing deal with Universal Music Publishing Group. With the labels, she released her second EP, The Walls Are Way Too Thin (2021), which marked her debut on the UK Albums Chart. All of the songs from both EPs were included on a compilation album, Can You Afford to Lose Me?.
In late 2023, Humberstone released her debut album, Paint My Bedroom Black. In 2024, as opposed to releasing a deluxe edition of the album, she released an EP with tracks that did not make the final track listing for the album, titled Work in Progress. Her second studio album, Cruel World, is set to be released on 10 April 2026. They were preceded by the singles "Die Happy", "To Love Somebody" and "Cruel World".