In early 2009, Pill's first mixtape4180: The Prescription, and his first single "Trap Goin' Ham" was released.[1] In September 2009, Pill was featured in The Source's Unsigned Hype section.[4] The mixtape received praise from fellow Atlanta rapper André 3000.[5] Later that year he was featured in XXL's Show & Prove section.[1] He also appeared on Killer Mike's Underground Atlanta compilation, on the tracks "Bunkin'" and "Grind Time."[1][6] Pill's second mixtape 4075: The Refill and his second single off the mixtape "Glass" was released.
In 2010, he was featured on the cover of XXL as part of the XXL Freshman 10 line-up, with Donnis, Nipsey Hussle, Jay Rock, J. Cole, OJ da Juiceman and more.[7] In June 2010, he released his third mixtape and first Gangsta Grillz mixtape 1140: The Overdose which was hosted by DJ Drama.[8] He later appeared on fellow XXL Freshman Freddie Gibbs's EP Str8 Killa No Filla on the track "Do Wrong."[9] He was also featured on "Introducing the Business" by Mark Ronson, which featured on Ronson's album Record Collection.
Maybach Music Group, the hip-hop imprint founded by Rick Ross, has announced a partnership with Warner Bros. Records. Maybach also announced its latest signee, Atlanta rapper Pill, on 22 February 2011.[10]
Recently Pill was featured on "Ya Killin Me", a song off of Tech N9ne's new All 6's and 7's album, which appeared as a bonus track.[11]
On 3 January 2012, Pill announced that he was leaving Maybach Music Group Imprint and Warner Bros. Records via his Twitter account.[12]
After a six-year hiatus, Pill released a single "Back Right" on 15 February 2018, produced by 808 Mafia.[13]