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One of Woody Allen's zanier latter-day films, the 2000 comedy Small Time Crooks follows a former criminal named Ray (Allen) and his wife, Frenchy (Tracey Ullman), poor but happy in their New York City apartment. Ray hatches an elaborate scheme: Rob a bank by buying the building next door and tunneling under it. To explain their presence, Ray has Frenchy set up a cookie shop as a front. Two days later, the tunneling is getting nowhere, but the cookie shop is a huge success!

While the plot shares some similarities with S. J. Perelman's play The Night Before Christmas (itself adapted to the screen as the 1942 comedy Larceny, Inc. with Edward G. Robinson), in true Woody Allen style this film is less about the heist itself and more about how Ray and Frenchy's relationship progresses in the face of their newfound wealth and status.

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Tropes:

  • Authority in Name Only: Tommy becomes the company's chairman of the board, but doesn't do anything more important than hiring a plumber to fix the office building's toilets.
  • Big Applesauce: The setting, as usual for Allen.
  • Brick Joke: Benny, a career arsonist, becomes the fire safety inspector for Sunset Cookies.
  • The Caper: The final quarter of the film is a jewel heist. They end up stealing the fakes they intended to replace the real one with.
  • Chekhov's Skill: Several people comment on Frenchy's cookies before she sets up the shop. Ray's teaching Frenchy in how to crack safes saves the day, too.
  • Cloud Cuckoolander: May is a major source of humor in the film.
    May: Then the lights begin to flash. Little pinpoints of light. Then my tongue turns black and I can't swallow.
    Dr. Henske: Really?
    May: The diagnosis is Parkinson's, but they think it could be the Ebola virus, or mad cow disease.
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  • The Convenient Store Next Door: The cookie shop.
  • Cut Lex Luthor a Check: Deconstructed and averted, as French's cookie selling becomes the big score, not the bank heist.
  • Dumbass Has a Point:
    • When Ray and May try to steal a socialite's necklace, they mix up the real one and the copy they plan to replace it with. Ray says that they can't take both necklaces because they've been seen acting suspiciously in close vicinity to the safe and will be the prime suspects if the necklace just disappeared.
    • Denny, a man who thinks Ray is a genius, is made head of advertising for the cookie company and focuses on putting ads in his favorite pornographic magazines, claiming that it will make readers associate the lust they feel with the cookies. Judging by how successful the company becomes, this idea seems to be working.
  • Fake–Real Turn: Again, the cookie shop.
  • Failure Hero: Ray. Frenchy, too, but she manages to save the day with one of the skills she learned from Ray. Safe cracking.
  • Genius Ditz: May is astonishly dumb, a master of Comically Missing the Point, but gives some Brutal Honesty with her "The Reason You Suck" Speech to Ray near the end.
  • Gold Digger: David, a rare male variant.
  • Haute Cuisine Is Weird: Ray wants no part of food "that leaves a slime trail" and just wants a cheeseburger.
  • Innocently Insensitive: May.
    Ray: I get a bad vibe about this guy, David. It's my street instinct, but I just don't trust him.
    May: Yeah, I know why. Because he's younger than you are, handsomer than you are, he's much taller than you are, he's smarter than you are, he's much more exciting than you are...
    Ray: May, don't feel obligated to pull any punches with me. I can take it.
  • Insurance Fraud: One of Ray's friends sent two of his children to college with money from that kind of fraud and was planning another insurance fraud when he decided to set this plan aside to help Ray with a bank robbery.
  • It Is Pronounced "Tro-PAY": Low class Frenchy calls crudites "crudd-iytes".
  • Let Off by the Detective: Ken, a cop who buys cookies from the store, figures out the gang's robbery scheme and catches them in the act of tunneling into the wrong building. He lets them go once they promise to stick to the cookie business and offer him a cut of it.
  • Line-of-Sight Name: The cookie business is called "Sunset Cookies" after Ray convinces Frenchy to be in on the scheme while on the roof during a beautiful sunset.
  • Nouveau Riche: Ray and Frenchy are the very definition! Even the caterer seems offended.
  • "The Reason You Suck" Speech: May gives Ray a thorough dressing down late in the film.
  • Small Name, Big Ego: Ray thinks he's a genius, and notes everyone in prison called him "The Brain". His former cellmates insist it was an Ironic Nickname.
  • Stupid Crooks: And small time, too. It's one of the rare movies in which Allen plays a complete idiot.
  • What Happened to the Mouse?: Denny, Benny, Tommy, and Ken all get jobs with the cookie company after the Fake–Real Turn, but disappear after a couple of scenes, and it isn't shown what happens to them after the company goes bankrupt.
  • Where It All Began: Ray and Frenchy end up from where they started from, but with a new appreciation for each other.

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