The first commercial appearance of the group was on Cam'ron's 2000 album S.D.E., released on Epic Records. During this period, various members of the original group consisting of Cam'ron, Jim Jones, and others, were first signed together as a group to Roc-A-Fella Records from 2002 to 2004, though they are now signed to their own label, Diplomat Records. Each individual artist, however is signed to a different label, including E1 Music, Asylum, and Def Jam, among others.
The group came to further popularity in 2002 with the release of Cam'ron's third album, Come Home With Me. The lead singles were platinum hits "Oh Boy" and "Hey Ma", which both featured group mate Juelz Santana. The group followed Cam'ron's solo album shortly after with their debut album Diplomatic Immunity released in 2003, which featured remixes of both songs, as well as lead single "Dipset Anthem" which peaked at #64 on the BillboardHot R&B/Hip-Hop Songs chart. The double-disc album was a success and quickly became certified gold by RIAA under two months after its release. By the time of the release of their 2004 followup, Diplomatic Immunity 2, additional members Hell Rell, 40 Cal., and J. R. Writer had joined the group.