Dee was relatively successful long before being on "Last Comic Standing". He had already had his own comedy special on The Comedy Network in Canada, appeared on the Comedy Network special "The Nubian Disciples", and performed at the world-famous Montreal Just for Laughs International Comedy Festival, having his segment aired on Just For Laughs. He has appeared in television commercials and has performed at many comedy clubs, including Just For Laughs and Yuk Yuks. Dee also had a role in the 2006 film "", where he played the role of Donny. That same year, Dee played former Boston Bruins player Wayne Cashman in the CBC miniseries "Canada Russia '72".