After making his debut in 2011 with the beat tape Bowser (Alpha Pup Records), he released the mixtape I Don't Care, which featured his own rapping, due in large part because he couldn't find any rappers to rhyme over his beats. In 2012 he signed with the Stones Throw label and released the instrumental album Oodles of Doodles. His first release for the label as an MC came in 2013 when he dropped the aptly titled Rap Album One.

Cassette on Vinyl, a compilation of his Cassette mixtape trilogy, was released in 2014. The nine-song collection featured guests Jeremiah Jae, Zeroh, and Oliver the 2nd. The Jonwayne Is Retired EP arrived the following year, featuring R&B singer Anderson Paak.

In 2016, Wayne kicked off a singles series, starting with "Wonka." Each release -- including "That's OK," "Jump Shot," and "40 Winks" -- featured the original track, a radio edit, and instrumental and a cappella versions. ~ David Jeffries & Neil Z. Yeung