James Kemsley was born in Sydney, before his family moved to New Guinea. He attending boarding school in Bowral and Rose Bay, and moved to Victoria with is father.

Kemsley studied acting at the Independent School of Dramatic Art, North Sydney (1969–1972) and in England at the Royal Academy of Dramatic Arts (1979). From the late 1960s he became well known to Sydney and Melbourne TV audiences as "Skeeter the Paperboy" in The Super Flying Fun Show and then as host of Skeeter's Cartoon Corner (Nine Network). He later compered the variety program Junior Cabaret and appeared in the ABC TV mini-series The Cousin From Fiji and Seven Little Australians. He wrote three successful children's plays.

In 1984 Kemsley was invited to take over the iconic syndicated newspaper strip Ginger Meggs, which he continued to draw until his death. He also contributed cartoons to papers such as Sunday Mail (Adelaide) and The Sun-Herald, The Sydney Morning Herald and The Daily Telegraph (Sydney).

Kemsley twice served as President of the Australian Cartoonists' Association and received its 2001 Stanley Award for Cartoonist of the Year. In 1990 and 2004, he received the Stanley for Comic Strip Artist.