Father Is a Bachelor (1950)

Carefree vagabond Johnny Rutledge (William Holden) is stuck in a small town when his medicine show employer and friend Professor Mordecai Ford (Charles Winninger) is put in jail. He befriends a young girl named May Chalotte (Mary Jane Saunders). She, her brothers January (Gary Gray) and February (Billy Gray), and her twin brothers March (Warren Farlow) and April (Wayne A. Farlow) are orphans. However, fearful of being separated, they haven't told anybody. Johnny finds himself being "adopted" as their uncle. Johnny starts working hard to support his new family, working on a farm during the week and singing and waiting tables on Sunday in a restaurant owned by Jericho Schlosser (Sig Ruman). Johnny makes the acquaintance of lovely heiress Prudence Millett (Coleen Gray) when she comes to inquire why the children are not in school. A romance begins to blossom, despite Johnny's determination to remain free of entanglements. When wealthy, unloved Jeffrey Gilland Sr. (Frederic Tozere) orders Johnny to keep his disreputable children away from his son Jeffrey Jr. (Tommy Ivo), Johnny scuffles with him and gets thrown in jail. He is bailed out by Prudence, but his troubles are not over. Plato Cassin (Clinton Sundberg) finds out about the children's parents and blackmails Johnny into agreeing to marry one of his older, spinster sisters, Genevieve (Peggy Converse) or Adelaide (Lillian Bronson), in order to keep the kids. (Adelaide wins a ring toss game for the privilege.) Plato also convinces Prudence that Johnny was using the children to romance her. After thinking it over, Johnny decides to run away with Professor Ford. May overhears and invites people to her birthday party, intending it to be a going-away party for Johnny. Prudence shows up, having seen how far Johnny is willing to go for the children, and suggests he marry her instead. Adelaide proves to be a sport; they toss a coin for Johnny. Prudence wins, and Professor Ford leaves town alone.