Miss Victoria Woodworth (Edith Evans) is an elderly New York heiress, living a quietly patrician life in her luxurious mansion 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 jerkass 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:
- Affectionate Nickname: "Fitzwilly" for Fitzwilliam, and "Miss Vicki" for Miss Woodworth.
- 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.
- Breaking the Fourth Wall: Right after the opening credits, Fitzwilly addresses the camera directly:"Once upon a time, the very privileged lived the way we [in Miss Woodworth's household] still do: in quiet luxury, elegance, grace. It's an almost vanished way of life. Not easy to hold on to. And terribly expensive to maintain."
- 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 Poyntz Tyler's 1960 novel A Garden of Cucumbers.note
- Flirtatious Smack on the Ass:
- Fitzwilly gives one of these to Juliet after kissing her.
- At Gimbels one of the crew creates a distraction by pinching the rears of various women in the crowd.
- 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.
- Money to Throw Away: One of Fitzwilly's crew does this outside one of Gimbels' store entrances to attract a door-blocking mob.
- One Last Job: The Gimbels Christmas Eve heist. Or, as Fitzwilly calls it, "Operation Get Out While You're Ahead".
- Properly Paranoid: Oberblatz, of the Gimbels security department, is very worried about the store getting robbed. And 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 Miss Woodworth and Fitzwilly lead. Justified in-universe as her disapproving of some of the official Cub Scouts’ rules.
- 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.
- Write Who You Know: In-universe, Miss Woodworth's dictionary doubles as a sub rosa memoir of her late father. Which is ultimately deemed entertaining enough to sell to Hollywood for a movie.