Jonwayne briefly worked as a stage actor after high school.[5] Through these activities, he developed a crush on a girl who was interested in poetry; he then began writing his own poetry in order to impress her and quickly found a passion for it. Jonwayne's love of poetry led to his involvement in hip hop at 17 years old when a rap group from West Covina began bringing their equipment to a Young Artists Workshop that he attended. In early 2009, he began frequenting Low End Theory, the Los Angeles club event where he would meet his friend and mentor, Dibiase. By 2010, he had booked his first gig at Low End Theory and became one of the youngest artists ever to perform there. He came to the attention of Stones Throw Records head Peanut Butter Wolf when the two were on the same bill at a benefit show at Low End Theory in 2010.[3]
He released his debut album, the instrumental Bowser, on Alpha Pup Records in 2011.[6] In that year, he also released a mixtape, I Don't Care.[7] It was included on Pitchfork's "Overlooked Mixtapes" list.[4] His 48-track instrumental album, Oodles of Doodles, was released on Stones Throw Records in 2012.[8] In that year, he also released a mixtape, This Is False.[9]
He has released a series of mixtapes, Cassette in 2012 followed by Cassette 2 and Cassette 3: The Marion Morrison Mixtape in 2013. The artwork for each mixtape mimicked the trade dress of recognizable products: a pack of Marlboro cigarettes (Cassette), a can of Coca-Cola (Cassette 2), and a first generation iPod (Cassette 3).[10] In 2013, Philip Morris USA sent a cease and desist letter to Stones Throw, alleging that the design of Cassette infringed its trademark in the Marlboro packaging design.[11] Stones Throw agreed to stop producing anymore copies of Cassette, noting that they were "just about out of tapes anyway."[12] "Cool Runnings", a track from Cassette 2, was included on Drowned in Sound's "Top Tracks" list in April 2013.[13]
