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, Juelz Santana, Freekey Zekey, and others, were first signed together as a group to Roc-A-Fella Records from 2001 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 Billboard Hot 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.

In December 2007, Jim Jones stated in an interview that even though there are controversies between various members of the group, there is a plan in motion to bring back "The Diplomats" in the future. Jones, who hasn't been on speaking terms with the group's leader Cam'ron, also stated that there have been various conversations on a plan for a third installment of the "Diplomatic Immunity" series. The album had been expected to be released sometime in the summer of 2008, though no such album materialized.

However, in a later interview, 40 Cal. hinted that while the dynamic of the group is likely beyond repair, there may be further collaboration. Juelz Santana also spoke on a future collaboration, but stated that at the moment, Cam'ron seems to be the only obstacle, while also stating that though his contract was sold to Def Jam, he has no hard feelings towards his former boss.

In a September 2008 interview, Juelz Santana stated that he no longer has a contractual obligation to Cam'ron and/or Jim Jones. Within the interview Juelz also stated that he is still on speaking terms with the members of the group, and didn't feel that they were holding him back, but he did feel the "mainstream" wasn't crediting him as notable as much as he had hoped. Though in a later interview, he stated that he felt the other members of the group were not as focused as he, while also stating there was selfishness within the group. He also stated he wanted to focus more on his career.

In April 2010, Cam'ron and Jim Jones announced they ended their feud. In June 2010, the Dipset reunion began with a teaser titled "Under Construction" and a street single, "Salute" produced by Araabmuzik. The song features Jim Jones, Cam'ron, and Juelz Santana.

In 2007, 40 Cal. started "Skeme Team", while Freekey Zekey formed the "730 Dips", started a record label of the same name, "730 Dips Records", while also joining fellow Diplomats' member Jim Jones new group, "ByrdGang".

In 2008, Juelz Santana started the "Skull Gang" which, when his contract was sold to Def Jam, also secured a deal, that included the solo members.In 2009 Camron started a new group called the U.N and Dipset West. In 2008 Hell Rell started Top Gunnas and J.R started Thundabyrdz.

In 2009, Cam'ron created The U.N. (Us Now), featuring himself and Vado among other Harlem rappers. The group has a debut album coming in Summer 2010, Gunz n' Butta'.

Mixtapes