Gaskill entered the world of newspapers via the Rand Daily Mail (Johannesburg) in 1973. This was the start of a cartooning endeavor which took him to many papers in many places, the more notable being The Sunday Times (Johannesburg), The West Australian (Perth), Herald (Auckland). Added to these were advertising and magazine assignments. Returning to Britain in 1987, Gaskill succeeded KAL as editorial cartoonist on the groundbreaking Today newspaper. Sadly, this paper closed in 1995 and Gaskill went freelance. Since then he has produced cartoons and illustrations for the Mail on Sunday, the News of the World and was the political cartoonist for the Sun for nine years until he was fired by Rebekah Wade.