Miss Victoria Woodworth (Edith Evans) is an elderly New York heiress, living a quietly patrician life in her plush brownstone with a large household staff and frequently engaging in philanthropy. There is one rather large problem with her lifestyle, however: she doesn't actually have any money. Her wealthy father left her a mere $180, and her loyal servants, led by Fitzwilly, have been engaging in elaborate schemes and scams in order to facilitate her lifestyle.
All of this threatens to unravel, however, when Miss Woodworth brings in Juliet Nowell (Barbara Feldon), an outsider to their servant network, to assist her in compiling a dictionary containing all possible phonetic misspellings. Trying to prevent Juliet from discovering their crimes, Fitzwilly courts her in order to persuade her to leave. Things become even more complicated when he begins to fall for her for real...
This film contains examples of:
- The Atoner: Former priest servant Albert, who, consumed with guilt over his crimes, turns himself in after the Christmas job.
- Belligerent Sexual Tension: Between Fitzwilly and Juliet, initially.
- The Caper: The film climaxes with an audacious plan to rob Gimbels department store on Christmas Eve.
- The Con: The specialty of the servants.
- The Film of the Book: Adapted from a novel called A Garden of Cucumbers.note
- I Need a Freaking Drink: When Juliet tells Fitzwilly that she let their boss give away $50,000 that the household can't afford to lose, they both sit down and down glasses of wine.
- John Williams: Composed the film's score, under the name "Johnny" Williams.
- Meaningful Name: The fake thrift store Fitzwilly and co. use to fence their stolen merchandise is called "St. Dismas", after the traditional name for the penitent thief at Christ's crucifixion.
- Mock Millionaire: Miss Woodworth lacks the money for her philanthropic promises, not that she's aware of it.
- One Last Job: The Gimbels Christmas Eve heist.
- Properly Paranoid: Oberblatz, who heads up security for Gimbels, is worried about the store getting robbed. Rightfully so, as it turns out.
- Satellite Character: Most of Fitzwilly's fellow thieving domestics receive little characterization beyond being his helpers.
- Scout-Out: The "Platypi" troop of neighborhood boys that Fitzwilly leads.
- Serious Business: Juliet's father and his best friend deeply obsess over their Scrabble games and resent any interruptions.
- Uncle Pennybags: Miss Woodworth, who is very generous with her philanthropy. Very generous. She's also not afraid to lightly blackmail the district attorney to go soft on her servant.
- Wealthy Ever After: In the end, the dictionary is turned into a screenplay and is sold to Hollywood, solving the household's financial problems.