During his high school days, Talmage had originally intended upon pursuing an acting career. His first effort in standup comedy was at the Polo Park Inn in 1984, after some friends persuaded him to get up and "tell a few jokes" as a contest, which he went on to win. After a number of successful comedy appearances at the Viscount Gort, he started his own agency named Comedy Connections, which had around nine comedians on its books and book appearances for them in Winnipeg. When
Yuk Yuk's opened in
Winnipeg, he sold his agency and joined them, first appearing at New Talent Night and was later hired by the club to do appearances around the city. His earlier material was described by him as being "dirty", though he later made it cleaner as he felt that gave him the best chance of getting television broadcasts. Short in stature (standing in height), he rose to become a standup headliner and for 15 years called Toronto his home-base. He traveled around the world performing and eventually ended up in South Africa, where he was writer, producer and star of situation comedy
Bachelor Pad. The sitcom, which featured sketches and celebrity appearances, won a prize on its script and a pilot of 13 episodes was shot. He later went touring around Hong Kong, New Zealand and Australia. Kerry toured with
Prince,
Bachman–Turner Overdrive,
Nash The Slash,
The Tragically Hip and
Doug and the Slugs. He was also featured on The Movie Network's Comedy Special
Mondo Taboo, CBC-TV's
Hour Magazine, CHCH-TV's
Comedy at Club 54,
MuchMusic and at Comedy Festivals in Toronto, Vancouver, Seattle and Montreal. While a writer for the Simpsons,
Conan O'Brien created a character on The Simpsons based on Kerry, a kidney patient by the name of Cornelius Talmage. Talmage reflected on the difficulties involved in making a living from being a comic, noting that comics may have to drive for hours around different clubs to perform for very little money, only after they have spent years performing for free to build a reputation strong enough that they can command a fee. He considered the possibility in the late 1980s of moving to Toronto or Alaska as he was told by numerous people that he could not make a successful career as a comedian in Canada, but he did not believe that to be true. He ultimately left his hometown in search of work further south as he felt that club owners were more focused on hiring "hot American acts" instead of home-grown "less-exotic" talent. ==Health==