Winsor McCay drew delightful drawings about the dreams of a Welsh rarebit fiend, 'rare bits' inspired by an overindulgence in cheese. Dreams of the Rarebit Fiend was a Saturday cartoon that appeared in the New York Evening Telegram from 1904 to 1911, psychic twin to Little Nemo in Slumberland that appeared concurrently in the Sunday Funnies of the New York Herald from 1905-1911. 'Slumberland' was a Neo-classical fantasy that closely resembled the idealized White City of the Chicago World's Fair (1893), that inspired the architecture of Coney Island's Dreamland (1905-1911), which beckoned to McCay as he drew from his house just across Sheepshead Bay in Brooklyn. The capricious side of this Architecture emerged in McCay's cartoons. A self-taught illustrator, McCay began his career in Detroit working in dime museums, worlds of wonder—filled with monsters—dioramas and sideshow performers whose livelihood depended on their ability to amaze an audience. Just this sort of rare and gifted fellow, McCay parlayed his entertaining lampoonery of Slumberland into some of the world's first animations on vaudeville. As with the Rarebit Fiend, Little Nemo's dreams were brought on by overindulgence, in his case of too many donuts or Huckleberry Pie. But, this was merely a pretense for McCay's fantastical 'dream' mode of thinking, a potentially useful body of knowledge that was simultaneously explored by Sigmund Freud, Henri Bergson and Marcel Proust, who linked the mechanisms employed by the unconscious in dreaming to those at play in wit. Architectural drawing—seen through McCay's cartoons and early animations—has a kind of 'gastronomical' alchemy that inadvertently became a treatise on the architectural imagination. Fiend and Little Nemo affected the psychic mood of early modern Architecture—its 'childhood' in the milieu of White Cities—that was both added to and commented on by Winsor McCay's pen. His cartoons portray the hidden 'flavors' of the buildings springing up a century ago. This 'other'—surreal—aspect of the White Cities, seasoned with whirling iron Ferris wheels and Flip-Flop rides, newly invented elevators and electric lights—and even fun house mirrors that made buildings suddenly seem very tall—were the ingredients that caused the fiend and Nemo to wake up, which ultimately became the culinary school of modern Architecture. McCay's 'fiendish' depictions show us that the right blend of humor and awe is a recipe for happiness. / Doctor of Philosophy / Winsor McCay made cartoons of the 'nightmares' of a Rarebit Fiend with a witty, unflinching eye for detail. Those illustrations became a psychic twin to the architectural fantasies of a little boy in the 'funnies' section of the New York newspapers from 1905-1911. Dreams of the Rarebit Fiend and Little Nemo in Slumberland continue to entertain and edify us, while inadvertently acting as a guide to how the imagination works. McCay's celebrity as a cartoonist also led him to become one of the world's first animators, amazing vaudeville audiences with depictions of Little Nemo that were suddenly larger than life, illuminated, and mobile. Dreams were rediscovered in the early twentieth century as useful bodies of knowledge for understanding the self, seen through the writings of Sigmund Freud, Henri Bergson and Marcel Proust, who linked the mechanisms employed by the unconscious 'dreamer' to those at play in wit. That thinking was surrounded by the atmosphere in McCay's comedic sequential images, which in turn inspired the iconic dreamlike silent movies of Buster Keaton. A look at the birth of these art forms a hundred years ago provides insight into the psychic mood of early modern Architecture, but also to the imagining of today's world (both material and virtual) using the digital tools that are just being invented. Although McCay's cartoons are fiendish, they sustain the balance between dreaming and humor that is essential to imagining a happy modern life.