Supasition was born in the small town of Greenville, North Carolina. He was an early fan of Hip Hop music and culture, and began rapping as early as 1986. In 1995, at the age of 18, he began to pursue a career in rap. Over the next seven years, he experienced severe industry mistreatment, receiving the runaround from various labels.
He spent 2 of those years waiting for his contract to expire after he was shelved by Davey DMX's (early RUN DMC producer) Lo Key Records. After a mutual friend introduced him to Cali emcee Rasco, he released the single "Broke Man's Anthem" on Rasco's imprint, Pockets Linted Entertainment. By 2002, he was finally able to release his debut album, 7 Years of Bad Luck, through Freshchest Records.
The title referenced the seven years he spent struggling in the music industry. The project was widely unnoticed and received moderate reviews.
In 2003, he appeared on Cunninlynguists acclaimed SouthernUnderground album. Supastition began receiving more wide attention in 2004, when he entered an Okayplayer record contest. His track "The Williams" (produced by Dutch producer Nicolay) was picked out of over 5000 entries as the winner, and was included on Okayplayer's True Notes, Vol. 1 compilation that year. Billboard Music labeled the song as one of the standout tracks on the compilation. In summer 2004, he appeared on legendary MC KRS-One's album Keep Right, on the song "Still Spittin'". In late 2004, he released an acclaimed EP titled The Deadline.
The single "Boombox" (great track) reached #2 on National College Radio charts and was featured on MTV2's One Life: The Love, The Game. He continued his exposure in 2005, appearing on projects from Little Brother (The Chittlin' Circuit and Separate but Equal mixtapes), Pumpkinhead and Cesar Commanche. In late 2005, he released his second full length album Chain Letters, featuring production from Nicolay, Jake One, Illind and M-phazes. The effort was one of the more acclaimed underground Hip Hop releases of the year. Chain Letters received high praise in magazines such as Scratch, XXL, Elemental, and many other highly respected publications.