From Barry County School he found work at the lithographic department at the Western Mail, mainly due to the fact that his father played golf with the chief executive of the paper, Sir Robert J.

Having already seen some of his artwork published in the Football Express before attending College, he now found himself drawing cartoons for the Western Mail and took on the role of deputising for the paper's celebrated political cartoonist J. M. Staniforth.

Illingworth then travelled to the United States and also undertook further art training in both Berlin and Paris, living in the latter for a while where he studied at the Academie Julian.

On returning to Britain Illingworth was in demand as a freelance artist seeing his work appear in not only many magazines, but also in advertising for firms such as Winsor & Newton and Grey's Cigarettes.

[2] In 1963 Illingworth was invited onto the popular BBC Radio 4 entertainment programme Desert Island Discs choosing a track by Wally Fawkes and his Troglodytes, a jazz band led by a friend and fellow Punch illustrator.