Dee was born Gerard Francis-John Donoghue, and is of Irish and Scottish descent. He was born in Scarborough and raised in Toronto. He was a university varsity hockey player and golfer. He attended St. Gabriel's (Bayview/Sheppard) and De La Salle College, Oaklands, where he later worked as a physical education teacher and hockey coach. He studied kinesiology and athletic therapy at York University and education at St. Francis Xavier University. His father was a bus driver for the TTC in Toronto for over 20 years.[citation needed]
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 Trailer Park Boys: The Movie, 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.[citation needed]
Dee placed third on the fifth season of Last Comic Standing. He had tried out for Last Comic Standing during the second and fourth seasons, but never advanced to the finals. He missed the birth of his daughter while appearing on the show. Since late 2007, Dee has had his own segment on Canadian cable channel The Score. These segments, entitled Gerry Dee: Sports Reporter, have Dee conducting humorous interviews and segments. The interviews have included such sports personalities as Charles Barkley, Michael Jordan, Wayne Gretzky, Cito Gaston, Randy Couture, and Chris Bosh.[citation needed]

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