Death Row Records Jones began his association with Death Row Records in March 1996 when he auditioned for Tupac Shakur in Las Vegas. Following Shakur's death in September 1996, Suge Knight offered Jones a contract with the label.He made his musical debut on the Gang Related soundtrack, appearing in two songs with rapper J-Flexx under the pseudonym Tenkamenin, sharing his name with a 11th century African Emperor of the Ghana Empire. In 1999 he performed several tracks on the Death Row collaboration Suge Knight Represents: Chronic 2000 alongside fellow Death Row artists Swoop G and Lil' C-Style. These songs had been written by Tha Realest for his solo project which was to be called Inside Out. He would again collaborate with them on yet another Death Row compilation titled Too Gangsta for Radio, appearing on the tracks "Fuck Dre" and "Fuck Hollywood". "Fuck Dre", seemingly a response to the Dr. Dre single "Forgot About Dre", insults many former Death Row artists and their affiliates, primarily Dr. Dre, Snoop Dogg, Nate Dogg, N.W.A and Eminem, who is an artist on Dr. Dre's Aftermath Records.

On October 17, 1999, while working on Suge Knight Represents: Chronic 2000, Tha Realest sustained relatively serious injuries to the foot, having been shot in a drive-by shooting after leaving the studio in which he had just finished recording a song with Tha Dogg Pound (Kurupt and Daz Dillinger). Dwayne "Draws" Dupree, a security officer working in the area, was also shot, but died shortly after.

After Death Row RecordsFollowing Suge Knight's release from prison, Tha Realest left Death Row Records in late 2001 to pursue a record deal in order to release his debut album, for which he had recorded approximately 150 songs. Tha Realest had difficulty obtaining a contract as labels were unwilling to associate with a former artist of Death Row Records and the notoriety it accumulated over the years. In 2002, Tha Realest formed his own record label, 2 Real Entertainment (later Omertà Entertainment). In 2004, he recorded a mixtape at Can-Am Studios with Mob Life Records artist 730 entitled From East 2 West which featured musical performances by Swoop G and New Child of Outlawz. It was released in early 2007.

Tha Realest was signed to Tru 'Dat' Entertainment in 2006, a company founded by Hysear Randell to seek and recruit talented individuals in film, music, fashion and sports. The music video for his debut single, "Eurry Now and Then" was released shortly thereafter. It