Five O. Henry stories, each separate. The primary one from the critics' acclaim was "The Cop and the Anthem". Soapy tells fellow bum Horace that he is going to get arrested so he can spend the winter in a nice jail cell. He fails. He can't even accost a woman; she turns out to be a streetwalker. The other stories are "The Clarion Call", "The Last Leaf", "The Ransom of Red Chief", and "The Gift of the Magi".

When billionaire Jean-Marc Clement learns that he is to be satirized in an off-Broadway revue, he passes himself off as an actor playing him in order to get closer to the beautiful star of the show, Amanda Dell.

Molly and Terry Donahue, plus their three children, are The Five Donahues. Youngest son Tim meets hat-check girl Vicky and the family act begins to fall apart.

Jim and Connie's postwar New York building troubles keep Jim from working on his novel. Ex-WAC from Jim's army days Roberta moves in, further upsetting Connie but pleasing Jim's friend Ed. Tenant Charley, who marries tenant Eadie, loans money to Jim to help him keep the building, money which this Casanova obtains from rich widows.

A Justice of the Peace performed weddings a few days before his license was valid. A few years later five couples learn they have never been legally married.

Former burlesque star May and her daughter Peggy dance in the chorus. When May has a fight with featured dancer Bubbles, Bubbles leaves the show and Peggy takes her place. When Peggy falls in love with wealthy Randy, May fears class differences may lead to misery.

The untold and intimate life story of one of the greatest American photographers of all time, Bert Stern. After working alongside Stanley Kubrick at Look Magazine, Stern became an original Madison Avenue 'mad man', his images helping to create modern advertising. Ground-breaking photos of Elizabeth Taylor and Richard Burton, Marilyn Monroe and Twiggy, coupled with his astonishing success in advertising, minted Stern as a celebrity in his own right.

A 65-year-old printer hatches an elaborate scheme to avoid forced retirement.