Whittlesea was a regular book cover artist in the 1960s and 1970s working for Heinemann, Newnes, Young World, Macdonald and Oxford University Press amongst others. He was one of the artists who illustrated Malcolm Saville's stories, beginning with Dark Danger (Heinemann, 1965) before going on to illustrate a number of Lone Pine adventures for Newnes and Merlin.
He was a regular contributor to World of Wonder and Speed and Power in the 1970s, for the latter producing a series of stunning paintings based on the science fiction stories of Arthur C. Clarke and Isaac Asimov in 1974-75. In the early 1980s, he illustrated the Make Science Magic series for Purnell.
Although he was painting whilst working commercially, he did not begin exhibiting until 1985 when his work appeared in the Royal Academy Summer Exhibition. In that same year he was elected a member of both the Royal Society of Painters in Watercolour and the New English Art Club, and won the Painter Stainers Award. In 1989 he was Ken Howard's Artist of Choice for an exhibition at the Art's Club, Dover Street, London and Tom Coates' Choice at the Mall Gallery in 1991. In 1991 he was a prize-winner at the Singer/Friedland/Sunday Times Watercolour Exhibition, where he had been selected on a number of occasions. In 1998 he was commissioned to paint the Wimbledon Lawn Tennis Championship.
Many further exhibitions have followed at the Royal Academy, Bankside Gallery, Mall Gallery, Langham Fine Art, Alresford Gallery, Royal West of England Academy, Royal College of Art, Chelsea Arts Club, Richard Hagen Gallery, Lennox Gallery and RONA Gallery.
In 2002, he won the Jans Ondaatje Rolls Award for Drawing at the NEAC Exhibition at the Mall Galleries, London.
Whittlesea has also written two books: The Complete Book of Drawing (Michael Beazley, 1983; reprinted in 1992 as The Complete Step-by-Step Drawing Course) and The Complete Watercolour Course (Windward, 1987; reprinted in 1992 as The Complete Step-by-Step Watercolour Course).
He has said of his work: "I use oil or watercolours for painting and pastels and charcoal to draw. I work on primed canvas or good watercolour paper using a variety of hog hair and sable brushes. I have a very traditional way of working. I often work on 6 or more paintings at a time and I draw regularly and work from paintings. Drawings can be around for years before I think of using them in a painting...
"I still find painting a very difficult activity. Its unpredictable. At the start of each day. I am not sure that anything good will result and I have given up on achieving a style. Whatever develop, happens. There is no clear idea or vision of how a picture will look."
In 2010, his work was chosen to be part of an exhibition to mark the 300th anniversary of St. Pauls.
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