Jon Connor began producing and songwriting at the young age of 10. In middle school he began selling his own mixtapes out of his backpack and from the trunk of his mother's car. With the support of his mother, at the age of 14 he founded his own independent record label named All Varsity Music. By 16, Connor had financed and created an in-house studio with money he earned through odd jobs in the neighborhood.

In 2005, Connor released his first official mixtape, “The Calling, Pt. 1: The Prequel.” He followed that with another mixtape “Everybody Hates Connor” in 2006. Then he released his third mixtape, “The Calling Pt. 2: The Second Coming” in 2008. In 2009 he would link up with basketball player Mateen Cleaves, then later basketball player Jason Richardson, and Kendall "Young Sav" Freeman, vice president of rapper Rick Ross' Maybach Music Group record label to official start a record label. All who currently either run or co-own it. In 2010, Connor released his fourth mixtape, the Entourage-inspired, “Jon Connor as Vinnie Chase: Season One.” “Connor as Vinnie Chase: Season One” was produced primarily by Connor and All Varsity Music producer Optiks.

In 2011, Connor released “Salvation,” a collaboration album with producer Rob "Reef" Tewlow, who has produced for 50 Cent and Bad Meets Evil in the past. The album was met with positive reviews from music critics. William E. Ketchum III of HipHopDX stated, "Salvation undeniably showcases a sincerity and hunger that are tough to find in much of Hip Hop today. If Connor continues to build on the skill set he already has, living up to his fictional namesake shouldn't be so far off." At the end of 2011, Connor released his fifth mixtape, a sequel to “Jon Connor as Vinnie Chase: Season One,” titled “Season 2.” The mixtape featured guest appearances from GLC and Freeway. The mixtape garnered 130,000 downloads on Bandcamp within three months.

In 2012, Connor released “The Blue Album,” a mixtape featuring him rapping over various Jay-Z instrumentals from the three “Blueprint” albums, “The Blueprint,” “The Blueprint 2: The Gift & The Curse” and “The Blueprint 3.” The mixtape title is also a play on words, referencing Blue City Club a group he leads. Later that year Connor released the second installment of his "Best in the World" mixtape series, “The People's Rapper LP,” which features him entirely rapping over classic Eminem instrumentals. The mixtape was executive produced and hosted by Don Cannon, also featuring guest appearances by his Blue City Club cohorts. The People's Rapper LP was met with positive reviews, with Andres Vasquez of HipHopDX deeming it "EP-worthy." Following the release of “The People's Rapper LP,” Connor toured the Midwest United States with rapper Big K.R.I.T.

In early 2013, Connor revealed that he was working on various projects including, first, his debut studio album “Unconscious State,” then “Unsung Heroes LP” a collaboration album with rapper Chris Webby, his second studio album and a collaboration album with Ski Beatz. In mid-2013, Connor released “Unconscious State” under All Varsity Music. The album featured guest appearances by Danny Brown, Chris Webby, Freddie Gibbs, Royce da 5'9", Talib Kweli and Smoke DZA among others. Production was handled by Connor himself, Mr. Porter, Brix and Optiks among others. Upon its release the album peaked at number 35 on the US Billboard Top R&B/Hip-Hop Albums and number seven on the Billboard Heatseekers Albums charts.

In 2013, it was revealed that Connor had recently been in the studio with Dr. Dre. Connor told MTV that the two immediately had chemistry in the studio, and after vibing in their over the following months, Dre signed Connor to his record label Aftermath Entertainment, which is distributed by Interscope Records. At the end of his freestyle during a cypher at the taping of the 2013 BET Hip Hop Awards on September 29, Connor revealed that he had signed to Dre's Aftermath Entertainment.

In 2014, Connor released another installment in his "Best in the World" series, the surprise mixtape “The Late Registration of a College Dropout Who Had a Dark Twisted Fantasy of 808s and Heartbreak.” Like his other “Best in the World” mixtapes, “The Late Registration of a College Dropout Who Had a Dark Twisted Fantasy of 808s and Heartbreak” was met with positive reviews from music critics.

Connor was chosen to be part of XXL’s 2014 Freshmen Class.

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