[5] Rountree was educated at Auckland's Queen's College,[citation needed] and began working at Wilson and Horton Printers in the city, designing show-cards, advertisements, and product labels.
[6]: 193 He progressed to become special artist for the Auckland Weekly News, published by Wilson and Horton, with his earliest signed drawings, quite serious in tone and subject matter, appearing in 1899.
Auckland is my native city and New Zealand is my nation... though it may be glorious for sheep, for the simple life, for lots of fun, yet it is no place for the black-and-white artist who wants to sell his wares.
It seems scarcely credible, and yet, though I had done hundreds of drawings before I made the voyage of twelve thousand miles to London, I had never seen an original — except my own — and I was simply dying to see the little bits of Bristol-board containing the work of the men I most admired in the English illustrated magazines and papers'.
He was awarded a second-class pass in July 1902, but by that time had already met Sam Hield Hamer, editor of Little Folks magazine, who invited him to illustrate his story 'Extracts from the Diary of a Duckling'.
[3] Rountree produced well-liked cartoons for the magazine Punch from 1905 to 1939, and also created advertising, posters and book illustrations for writers such as P. G. Wodehouse and Arthur Conan Doyle.
His drawings and paintings in this specialised field bore the authentic stamp of deepest study and intimate familiarity of these subjects; the expression of anatomical diversity, with the constructional variety of fur and feather revealed the sum of a lifetime's keenest observation...To his animals and birds he often gave a whimsical or semi-human twist which has made them loved by generations of children...
When first I knew him some twenty years ago at the London Sketch Club and The Savage his charming personality, the wit of his drawings and rare ability as a raconteur made him outstanding in a group which included such names as John Hassall, W Heath Robinson and Lawson Wood.