Rock released his commercial debut single, "All My Life (In the Ghetto)" in late 2008, featuring fellow American recording artists Lil Wayne and will.i.am. The single was promoted as one of "iTunes's Free Downloads" in early 2009. In 2010, Rock was featured on the cover of XXL's annual Top 10 Freshmen issue. He was also named by MTV one of 2010's breakthrough MCs. Jay Rock was featured on Omarion's song "Hoodie" and was supposed to be featured on Flo Rida's third studio album Only One Flo but was left off the final tracklisting.
Rock's mixtape Tales From the Hood 2 went to iTunes on March 28, 2010 and his mixtape From the Hood to the Cover of XXL was released to iTunes on July 24, 2010. He also toured with 50 Cent, and other rappers on The Invitation Tour. Around the same time he left Warner Bros. due to them delaying his album. Jay Rock then signed with indie record label Strange Music in the Fall of 2010, on a multi-album deal after leaving from Warner Bros. Jay Rock then went on tour with Tech N9ne, E-40, Glasses Malone, Kutt Calhoun and Kendrick Lamar on the "Independent Grind National Tour". His mixtape Black Friday, was released December 7, 2010 to iTunes.
During 2012, Rock toured with the rest of Black Hippy and MMG artist Stalley, on BET's Music Matters Tour. In October 2012, Rock's appearance on Kendrick Lamar's major-label debut, good kid, m.A.A.d city, was highly significant as he was the only other rapper from Black Hippy, to be featured on the standard edition of the album. Rock is featured on the song "Money Trees", for which his verse was highly acclaimed. He would later perform "Money Trees", with Lamar, at the 2013 BET Hip Hop Awards, along with appearing in the TDE Cypher. XXL named his verse the fourth best of the night.
In November 2013, Rock told Power 105 that his second studio album would be released in 2014. With the release of the 56th Annual Grammy Awards nominations, it was revealed Rock was nominated for Album of the Year as a featured artist for participating on Kendrick Lamar's good kid, m.A.A.d city. After the release of label-mate Ab-Soul's album These Days... in June 2014, TDE's CEO confirmed that Jay Rock would be the next artist from the label to release an album.
In September 2014, Tech N9ne revealed that Rock had left his Strange Music imprint and is now only signed to Top Dawg Entertainment. On October 29, 2014, Jay Rock released a song titled "Pay For It", featuring Kendrick Lamar and Chantal Kreviazuk, as a promotional single. On November 15, 2014, Rock appeared on NBC late-night live television sketch comedy and variety show Saturday Night Live, alongside the musical guest Lamar, where they performed "Pay For It".