The North Philly MC first signed to Roc-A-Fella Records in 2001 with the help of Freeway, a friend of Peedi since high school who had already joined the label through Beanie Sigel and his State Property entourage. In 2002, Peedi's Megahertz produced debut single, "One for Peedi Crakk," charted in the R&B/hip-hop Top 40. He continued to make appearances on various Roc-a-Fella albums, including Jay-Z's The Blueprint: The Gift & the Curse and Freeway's Philadelphia Freeway. His guest appearances were usually standouts, and his mixtapes gave him a reputation among East Coast rap fans. Faced with increasing exposure, the Philly rapper decided to modify his rap name to Peedi Peedi.

In 2006, Peedi was featured on Game Theory, the first Def Jam release by fellow rap group The Roots, on its single "Long Time". Shortly afterwards, Roots drummer and leader ?uestlove offered Peedi a provisional spot with the group.