Chicago MC Vakill was born Donald Mason on the city's near south side in 1975. He discovered hip-hop in his early teens, favoring the kind of literate, ingenious rhymes he would later pursue with his own music.

In high school Mason teamed with classmate Ed Zamudio, and their collaboration continued after Zamudio co-founded the Molemen collective (adopting the alias Panik in the process). In addition to his 1995 debut cassette, Who's Afraid?, Vakill appeared on a series of Molemen-helmed comps and mixes, most notably joining forces with Percee P and Rhymefest for the 1996 single Keep the Fame.

Despite renown in underground circles for his terse rapping and razor wit, Vakill remained a largely unknown quantity until the 2003 release of his first full-length effort, The Darkest Cloud, which slowly built buzz in the months to follow.

With his cult following blossoming, the rapper finally resurfaced in early 2006 with the acclaimed Worst Fears Confirmed.