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.