Some critics have dismissed this story of a man who escapes his worldly woes by fleeing his office to return to his small-town, rundown origins as "pure trash," but we uncover some historical reasons it should be of interest. First, "John Jackson's Arcady" was the last short story Fitzgerald wrote in April 1924 before departing for the Riviera to write The Great Gatsby. As such, it has some intriguing overlap with the novel. Second, although not republished in a collection until 1979, the story enjoyed a curious afterlife as an elocution text for aspiring high-school orators (and Rotarians). But third and most importantly, the story's closing scene in which John Jackson discovers just how much the world appreciates the good deeds he's done may just be---oh heck, we'll go on a limb and say we're ninety percent certain it is---the inspiration for Frank Capra's It's a Wonderful Life, starring (of course!) Jimmy Stewart. We explore that tantalizing connection, as well situate the story in the very popular 1920s' genre of the "revolt from the village." We also ask why "Arcady" is the rare sympathetic portrait of an American businessman at a time when nonfiction bestsellers such as Bruce Barton's The Man Nobody Knows (1925) proclaimed Jesus the quintessential entrepreneur. Along the way, after figuring out how to pronounce "Arcady," we quiz each other on famous Jacksons, from Stonewall to Tito to Luscious.