Penelope
Penelope Elcott (Natalie Wood) is the wife of wealthy banker James Elcott (Ian Bannen). Penelope decides to disguise herself as an old woman and rob her husband's bank. While the police, including Lieutenant Horatio Bixbee (Peter Falk), rush to get to the bank, Penelope escapes in a red wig and yellow suit. She donates some of the stolen money to a Salvation Army worker and donates the suit to a second-hand thrift shop. Con artists Sabada (Lila Kedrova) and Ducky (Lou Jacobi) immediately recognize the suit as an original designer outfit from Paris, and purchase it for a mere $7. Penelope visits her psychiatrist Gregory (Dick Shawn) and tells him all about her criminal activities. She says it began in college when a professor (Jonathan Winters) lured her into his laboratory and attempted to rape her, but she escaped, leaving her dress ripped off in the process. During the chase, she stole the watch fob of the professor. She next stole on her wedding day. When she caught her maid of honor Mildred Halliday (Norma Crane) kissing James, she swiped Mildred's earrings and necklace. Gregory suggests she is stealing to attract attention from her distant husband. A young woman, Honeysuckle Rose, is accused of being the thief. Gregory wants to return the stolen money to the bank, but panics when he hears police cars arriving. Penelope confesses and tries to clear the innocent Honeysuckle, but Horatio the cop and husband James do not believe her. Ducky and Sabada pay a visit, trying to blackmail her, but Penelope foils their blackmail attempt. Penelope hosts a dinner party, having stolen from all the invited guests. She tries to return the stolen items, but all claim that they never have seen them before. Penelope, confused and frightened, runs away. She again robs James' bank, but unlike the previous time, she is crying. James begs Horatio to find her. Penelope goes to Horatio with the stolen money, but the cop knows James would not press charges against his own wife. The psychiatrist explains the dinner guests denied recognizing the stolen items because they would lose the fraudulently inflated insurance claims they collected. Gregory breaks down and begs Penelope to run away with him. She refuses, telling him she is cured. James realizes that he has neglected Penelope and starts seeing her face everywhere he turns. He goes to the psychiatrist's office, where James and Penelope happily reunite.
