Chris Riddell was born in 1962 in Cape Town, South Africa, where his father was a “liberal Anglican vicar” and was opposed to the system of apartheid. The family returned to England when Chris was one year old, where he spent the rest of his childhood with his sister and three brothers, who now live in South Africa, Brighton, and Egypt. He attended Archbishop Tenison’s Grammar School in Kennington. Chris displayed artistic talent from an early age and was encouraged in this by his mother. As a child, he admired the work of Sir John Tenniel, the first illustrator of Alice in Wonderland, and W. Heath Robinson. At Brighton Polytechnic, he studied illustration; one teacher was Raymond Briggs, an earlier winner of two Greenaway Medals.

Riddell worked as an illustrator at The Economist in the 1980s, and at the Observer starting in 1995. In 2002, he named as influences Tenniel and E. H. Shepard, the first illustrator of The Wind in the Willows and Winnie the Pooh.