2005–2008: Nouveau Riche and ''Lupe Fiasco's The Cool'' After graduating in 2005, Jean was invited to perform at a
Labor Day barbecue in
Philadelphia by
The Roots. 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. Jean accepted the offer and moved to the city, where she lived in the neighborhood of
Manayunk. The five-member Nouveau Riche released two
extended plays (EPs) when it was active from 20052008. As the lead singer, Jean co-wrote many of the band's songs. Jean was working with producers Chris & Drop, who played one of Jean's songs to rapper
Lupe Fiasco. Fiasco invited her to collaborate with him. She featured on two tracks on his album ''
Lupe Fiasco's The Cool'' (2007): "Little Weapon" and the single "
Hip Hop Saved My Life", which she co-wrote. She later went on the tour for the album. Jean and Fiasco performed as one of the opening acts in
Kanye West's 2008
Glow in the Dark Tour. She believed her lack of mainstream success helped her secure collaborations, which allowed her to approach each writer as a fan. She was originally signed to Columbia Records but was let go in late 2010 as her music seemed "more mature" than they anticipated; the album was instead released on July 12, 2011 by indie label
S-Curve Records, titled
Pennies in a Jar. its songs failed to chart except in Japan, where it reached the Top 10 singles. Hollander would later write in his autobiography, "In my mind, I'd totally failed Nikki. [...] I'd under-thought the greatest idea ever and hung her out to dry in the process. She deserved better. This was easily the biggest miss of my career, and man, it stung."
2011–present: Extended plays and further collaborations Jean later moved to
Los Angeles. She released the
X-Mas EP in 2013,
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.
Jake One,
Like,
Double-O,
Donnie Trumpet and Nate Fox serve as producers. She featured on several songs on Lupe Fiasco's 2015 album
Tetsuo & Youth. Jean, Fiasco and The Roots performed "Little Death" on
The Tonight Show Starring Jimmy Fallon in February 2015. She and Fiasco also appeared for the first season of
Why? with Hannibal Buress (2015). Jean later featured on songs from Fiasco's 2018 album
Drogas Wave. In 2019, Jean released the seven-track EP
Beautiful Prison through
Rhymesayers Entertainment, with Fiasco featuring on the Jake One-produced single "Mr. Clean". She also released a short film called
Get Free. == Musical style and influences ==