It is not clear what training Webb had, but as both his uncle and grandfather were distinguished artists Kirkpatrick says that it was highly likely that they taught him.
They had five children, one girl, Florence Mary Ellen (1891), and three boys: Henry James Frederick (1894); Robert John (1900); and Archibald David (1905).
He was sometimes distinguished from his grandfather (who only died in 1883 at 91 years) with the suffix Junior[8] He was elected a member of the Royal Society of British Artists in 1890,[11] entitling him to use RBA after his name.
Kirkpatrick states his first book illustration for The Life and Strange Surprising Adventures of Robinson Crusoe by Defoe.
[12] Webb, together with J Finnemore, and D. Thompson illustrated this very beautifully printed and in every way luxurious edition – Bristol Mercury.
Nister also brought out My Robinson Crusoe Story Book: retold for the little ones by L. L. Weedon with colour plates by an unidentified artist, and black and white drawings by Webb.
This book is in the digital archive of the Baldwin Library of Historical Children's Literature in the University of Florida, here it has been dated as c.