BIO  Vakill was raised on the South side of Chicago on 119th Street and was involved in hip hop at as early as eight years old, originally focusing on the break dancing element of the culture. So while the culture continually evolved through the '80s and the music began to take center stage, Vakill began focusing rhyming, and found inspiration from respected lyricists such as Kool G Rap, Pharoahe Monch and Nas. In 1991, the young emcee met a high school classmate named Ed Zamudio at a local weekly event called Terrordome. Zamudio, later known as Panik, and Vakill, along with producers Memo and PNS, soon formed the Molemen, which would become one of the most prominent collectives in Chicago hip hop.

Vakill debuted as a solo artist in 1995, with the release of a cassette titled Who's Afraid?. He remained on the local scene throughout the late '90s, making numerous collaborations, and releasing a number of singles, most notably 1996's "Keep the Fame", a collaboration with veteran emcee Percee P and future Chicago hip hop star Rhymefest. In following years, Vakill contributed tracks to subsequent releases by the Molemen, with "Final Thought" appearing on the 1997 EP Below the Ground, "Know the Bidness" appearing on the 1998 EP Buried Alive, "Urban Legend" appearing on the 2001 album Chicago City Limits, Vol. 1, and "The Equinox" and "Face Down" appearing on the 2001 album Ritual of the Molemen. 2001 saw the release of a Vakill compilation titled Kill Em All, featuring all the tracks from Who's Afraid?, as well as a number of songs and freestyles recorded throughout the '90s. 

Vakill released his long-awaited debut album, The Darkest Cloud, in 2003 on Molemen Records. The album was produced by Molemen members Panik and Memo, DJ Contakt and Mixx Massacre, and featured the single "End of Days". The album's sharp lyrics and dark production made it a hit with underground fans, and gave the rapper the most exposure of his career. While acclaimed, the album did not reach past rap's underground scene, and failed to produce a significant amount of sales. The rapper returned three years later with his second album, Worst Fears Confirmed, released in early 2006. The album featured production from the Molemen, as well as appearances from acclaimed lyricists Ras Kass and Royce Da 5'9". Reception for the album was overwhelmingly positive, with Allmusic and Prefix Magazine both giving the album a 4½ star rating. The album gave the rapper wider media exposure, leading to features in XXL Magazine and on AllHipHop.com. Vakill was also featured in the Phat Tape section of the November 2006 issue of The Source Magazine, and in its Off The Radar section in the July issue. Vakill released his third studio album The Armor of God in 2011.