Ruff Ryders' founders were initially famous for managing rappers DMX, Ma$e, Jay-Z and The Lox who became multi-platinum stars for Def Jam Recordings and Bad Boy Entertainment in the late-1990s. After DMX's success, the management company started its own label imprint through Interscope Records, and had success with releases from female rapper Eve, former Bad Boy Records group The L.O.X. and its main rapper Jadakiss, Drag-On, and newcomer Jin, winner of BET's 106 & Park freestyle MC battle competition. The Deans' nephew Swizz Beatz is the main producer for most of the acts on the roster. In 2001, Cassidy was signed to the label through Swizz Beatz along with Full Surface labelmate Yung Wun.
As the first Reunion Project since their 2005 Album The Redemption, Vol. 4 Jadakiss and Swizz Beatz invited Drag-On, Eve, Styles P, Sheek Louch and DMX, who had just been released from jail, for the Remix of "Who's Real". A Ruff Ryders Reunion Album was announced by Swizz Beatz and was originally set to release in 2008 but it got pushed back.
In 2010, founders Joaquin and Darin Dean decided to revamp the brand through a new venture known as Ruff Ryders Indy, as a Fontana/Universal affiliated distribution company. This marked the end of Ruff Ryders Entertainment.