In 2002, under a new pseudonym, the singer released an album, Attack of The Attacking Things. During that period and throughout her career, the artist worked with such hip-hop artists as Atmosphere, The Roots, Styles P, Talib Kweli, Da Beatminerz, The Herbaliser, Phonte, Royce da 5'9, Mr. Len, Masta Ace, Vordul Mega, Pharoahe Monch, and many others.
In 2004, Jean presented a new LP, This Week. The album was successful. At that time, many clubs tried to book Jean Grae for private events.
Grae began working on her new album, Jeanius with the rapper 9th Wonder. However, part of the album was stolen and uploaded to the internet. Artists decided to stop working on it. Later, at one of the parties, Jean said that she is planning to release Jeanius sometime later.
In 2005, while working with Babygrande Records, she signed a contract with another label, Blacksmith, which belonged to Talib Kweli.
In April 2008, Jean used MySpace to announce that she is planning to leave the word of music. The singer explained that she was disappointed in the music industry and wanted to have a family. After some time, when it became obvious that Grae wasn’t going anywhere, the singer declared that she suddenly changed her mind.
The LP, Jeanius, the release of which was canceled back in 2005, eventually came out in 2008. An American critic Robert Christgau gave it excellent reviews. Other music magazines also had positive things to say about the release. The same year, the singer presented an improved version of the LP, which she called The Evil Jeanius. It was created with the assistance of a successful production duo, Blue Sky Black Death.
After taking a break, in June 2011, Grae presented a free mixtape, Cookies or Comas, which was recorded with Styles P, Pharoahe Monch и Talib Kweli. It featured such hits as "Assassins" from Kweli’s LP Monch's WAR and "Uh Oh" from his Gutter Rainbows.
In 2012, Grae released a compilation album, Dust Ruffle, which featured unreleased songs, recorded between 2004 and 2010.
In the fall of 2012, Grae released several EPs from Gotham Down series. Later, she combined them to create a compilation album, Gotham Down Deluxe.
At the end of 2012, the singer announced the name of her upcoming album, Cake or Death. However, it was never released.
In January 2014, Grae recorded an audiobook, The State of Eh, and starred in an online-comedy Life With Jeannie, which she wrote the script for.
In September 2018, Jean and an American rapper Quelle Chris released a joint album, Everything's Fine. It made its way into Rolling Stone’s 2018 top hip-hop album list.
