John McCaskey, a street sweeper living in O. Henry's New York neighborhood once aspired to be somebody. Today he can barely hold his job or stand up to his wife Maggie. John's only joy comes from filling a neighbor boy with fanciful tales about serving with General Custer at the Little Big Horn massacre.

"The O. Henry Playhouse" is a 1957 single season, 39-episode TV series. O. Henry (William Sydney Porter) is considered one of America's greatest writers of short stories. His writings are laced with humor and irony and often end with a sly twist ending. Veteran character actor Thomas Mitchell stars in each episode as writer O. Henry himself as he relates his stories to his publisher, his housekeeper, a barber, a bartender, or the cop on the beat. In some episodes, O. Henry meets his characters as he discovers firsthand the story he will later write. This unique storytelling method gives great insight into the famous author's creative process.