Miss Leeson is a young woman who works as a freelance typist with the big firms in the city. Her income is, however, insufficient to get her decent lodgings, so she is forced to rent what experienced house hunters call "the skylight room". The skylight room is a "well of stygian blackness", a sort of black hole where once light enters, it just dies in agony. The only source of natural light here is a small rectangular skylight. The skylight room has no windows; a small door leads to the landing. For a bright, vivacious and whimsically imaginative girl like Miss Leeson, this is the worst it can get. The bare room has a small cot, a wash stand and a dresser- all that Miss Leeson can afford. On the floors below live the more affluent lodgers of the sharp tongued and snobbish Mrs. Parker, Miss Leeson's landlady. Mr. Skidder is a playwright, perpetually on the lookout for a muse. Miss Leeson fits the bill, and the heroine of Mr. Skidder's next play becomes a short, happy-go-lucky woman who has long auburn hair. Mr. Hoover, a fat, middle aged man, is not above taking advantage of poor young girls, and the young Mr. Evans develops a boyish infatuation toward this woman whose fancies are forever skimming the skies and the stars.

Another one of O Henry's delightful stories, The Skylight Room is a modern day fairy tale, set in the heart of the author's favorite city, New York. A girl moves to the city looking for a friend she had lost track of and finds him in a very unusual way. This heartwarming tale describes the dream come true romance of Miss Leeson, a poor working girl in New York.

William Sydney Porter (September 11, 1862—June 5, 1910), known by his pen name O. Henry, was an American writer. O. Henry's short stories are known for their wit, wordplay, warm characterization and clever twist endings. The best known ones are A Service of Love, The Cop and the Anthem, The Furnished Room, The Gift of the Magi and The Last Leaf, which help him win fame abroad.

O. Henry's stories are gems of their kind; mellow, humorous, ironic, ingenious and shot through with that eminently salable quality known as 'human interest.'" —Bennet Cerf and Van Cartmell