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In 2004, Diggz signed with independent record label Maxamus Records, that year he released his first single “Hypnotic” which became an underground Toronto anthem. In 2005, Diggz released his hit single “Push It Up”, and was recruited to be a support act for Aftermath/G-Unit recording artist Game for his National Canadian Tour (18 Cities) as a result. In 2007, JDiggz released Memoirs of a Playbwoy, featuring the singles "Push It Up", "Make It Hot", "With You", "Gimme Dat" and "Just Wanna Party". The album, before its release, was titled The Pornstarr LP. In 2011, Diggz collaborated with Neverending White Lights frontman Daniel Victor on the song “This Time”, winning him his first major award for Independent Video Of The Year, at the 2011 Much Music MMVAs.