[1] Her father, Wyatt Cheek, worked in music marketing and promotion for entities including Select Records and Kiss FM;[1] her grandmother ran a liquor store;[2] and in the 1950s her grandfather owned a neighborhood jazz club.

[13] She transferred to the American Studies program, where her major included a concentration in visual, audio, literary, and performance cultures;[14] in 2011, she completed her Bachelor of Arts degree with distinction.

[5] In 2018, L'Rain (represented by Cheek and Ben Chapoteau-Katz) collaborated with producer Morgan Wiley and vocalist Patrick Gordon to remake the 1980s Chicago house track "Your Love" for a benefit compilation which paired electronic artists with formerly-incarcerated singers.

[36][13] (The project was conceived by Otabenga Jones and Associates in homage to Jitu Weusi, black nationalist community arts center The East, and the Central Brooklyn Jazz Consortium.

[39] In 2016, Cheek joined the curatorial team at contemporary art institution MoMA PS1;[40] the same year, she also opened the basement of her Brooklyn apartment to experimental music events under the name 49 Shade[41] (initially co-organized with Max Alper, Dann Lawrence, and Matteo Liberatore[13]).

At PS1, Cheek co-organized Sunday Sessions and the Warm Up series through 2021;[42] Warm Up lineups receiving extensive media coverage included a 2017 event with Cardi B, A$AP Ferg, and YATTA (of artist collective PTP);[43][44] a 2018 show pairing Lizzo with experimentalists Gang Gang Dance;[45][46] 2019's season opener, with Queens local duendita and Freddie Gibbs;[47] 2020's livestream edition, with Eartheater and KeiyaA;[48] and a limited-capacity 2021 event with Baby Tate and Patia's Fantasy World.

[10] AllMusic described L'Rain as making "dreamy, genre-blurring music [...], reflecting on grief, change, joy, and resistance through a collage-like mixture of soul, psychedelia, gospel, musique concrète, and numerous other genres.

"[56] Pitchfork described her 2021 album Fatigue as "painterly and methodical, daubing vocal loops over clattering percussion, sweeping strings, and resonant synths to create a shapeshifting strain of experimental pop.