The film's screenplay was based on the true short story "Uncle Clem's Boy" by Rogers' widow Betty Blake, which was published in The Saturday Evening Post in 1940.

Bing Crosby secretly made a screen test for the lead role in 1943 (available for viewing at the Paley Center for Media in New York City and Los Angeles), but Warner Bros owned the rights to the Will Rogers story while Crosby was under contract to Paramount and, in 1941, he had given up the clause that had allowed him to make one independent movie per year.

After the Great Depression strikes, Will works long hours flying around the country to perform benefit shows lifting the spirits of the American people and raising funds for the poor.

Bosley Crowther of The New York Times wrote that there was "not much action," but that Will Rogers Jr. was "vastly natural" in the part, and while "not an important film" it "gives a tender reflection of a character many people loved.

"[5] Variety called the script "a sketchy affair," but thought that Curtiz' direction "does a good job in presenting nostalgia, drama and humor, with only occasional slopping over into sentimentality.

"[8] The Monthly Film Bulletin wrote: "Rogers was in turn performer in wild west shows, successful Ziegfeld star, dabbler in popular politics, aviation enthusiast, great movie box-office attraction and 'favourite son' nominee for the American presidency, but Will Rogers Jr. impersonates his father with an indolent lack of charm that fails entirely to create a character interesting enough to hold these straggling episodes together.