Dudley D. Watkins was born on February 27, 1907 in Manchester, England.

After studying at the Nottingham School of Art he moved to Scotland in 1925 to attend classes at the Glasgow School of Art. He later began work with D.C. Thomson as a cartoonist. He created the Oor Wullie and The Broons comic strips for The Sunday Post newspaper in 1936, as well as illustrating the Desperate Dan strip for The Dandy comic, launched in 1937.

His workload was further increased when D.C. Thomson created the Beano comic the following year, with Watkins being responsible for drawing the Lord Snooty strip. When the Beezer and Topper were launched in the 1950s, Watkins was responsible for illustrating the Ginger strip (based largely on Oor Wullie, but unlike that strip the text was written in standard English and not in Scots vernacular) and the Mickey the Monkey strip for the two comics.

For many decades, Watkins (along with Allan Morley ) was the only cartoonist employed by D.C. Thomson allowed to sign his work, which was known for its intricate detail and unique style.

He worked with D.C. Thomson until his death on August 20, 1969.