Sampson first emerged in the early 2000s as a member of the group Rhythmicru, who released several independent albums which were popular in the Toronto hip hop scene.
[3] He then joined forces with some of Canada's most prominent hip hop producers, including Classified and DJ Kemo of The Rascalz and opened for such acts as Guru from Gang Starr, Maestro Fresh-Wes, The Hilltop Hoods, Eyedea & Abilities, and Scratch from The Roots.
[8] Sampson's second album, The Big Picture which focused primarily on global issues such as war, technology and economics, was also very well received.
[9] In his youth, Sampson had a small acting role opposite Vince Vaughn in the feature film A Cool, Dry Place.
Despite his lack of previous experience, he was given the role of a high school basketball player named "Peter".