Born in Saint Paul, Minnesota, Jean started out as a lead singer of a short-lived Philadelphia band called Nouveau Riche.

After two years of co-writing songs with many different songwriters for her debut album, including Bob Dylan and Carole King, Jean released Pennies in a Jar in 2011.

[2] Jean developed an early interest in songwriting after watching Irving Berlin's 100th birthday in 1983,[2][5] and started learning the piano aged eight.

Their member Dice Raw asked Jean to join his new band called the Disease (renamed Nouveau Riche two weeks later) after hearing her play piano in a studio.

[8][6] Jean's collaborations with Fiasco helped her gain wider recognition: a Billboard journalist wrote in 2011 that she was "previously best-known for her singing/writing stints on [The Cool].

[8] In 2008, Jean sought out producer Sam Hollander for his work on Carole King's 2001 album Love Makes the World to discuss a direction for a future solo career.

[1][14] She appeared on the Late Show with David Letterman, Tavis Smiley, Weekend Edition Saturday and Live from Daryl's House to promote it.

[11] While the album received positive reviews from music journalists,[2][15][16] its songs failed to chart — except in Japan, where it reached the Top 10 singles.

[20] Vibe premiered the extended play of the same name on November 19, 2014, containing six songs which concern topics such as police shootings, heartbreak and religion.

[25] In 2019, Jean released the seven-track EP Beautiful Prison through Rhymesayers Entertainment, with Fiasco featuring on the Jake One-produced single "Mr. Clean".

[26][27] A soul and pop artist and songwriter who often features on hip-hop songs,[8] Alison Stewart of The Washington Post described Jean as a "parallel universe's offspring of Carole King and Janelle Monae".