Boldy James' first big break on the national scene came in the form of 2 features on The Cool Kids and Don Cannon 2009 mixtape Merry Christmas, on the songs “BBQ Wings” and ”Tires”. That was followed up by his record “Gettin Flicked” appearing on The Cool Kids’ 2010 mixtape Tacklebox. Also in 2010 he was featured on the Chip tha Ripper song “Fat Raps” remix alongside Big Sean, Asher Roth, Dom Kennedy and Cool Kid member/producer Chuck Inglish (Boldy James and Inglish are cousins).
On May 24, 2011, Boldy James released his solo debut mixtape Trappers Alley Pros and Cons. The project went on to be named by Pitchfork as one of 2011′s Most Overlooked Projects. On February 27, 2012, he released his follow up mixtape, Consignment. On March 5, 2013, he released an EP titled Grand Quarters. On October 15, 2013, he released his debut album, My 1st Chemistry Set entirely produced by The Alchemist. On May 22, 2014, it was announced that Boldy James, Bishop Nehru, and Fashawn were the first signees to Nas' Mass Appeal Records.