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! True to Woody Allen style, this movie is more about how Ray and Frenchy's relationship progresses in the face of their new success and wealth.
- Big Applesauce: The setting, as usual for Allen.
- Brick Joke: Benny, a career arsonist, becomes the fire safety inspector for Sunset Cookies.
- Chekhov's Skill: Several people comment on Frenchy's cookies before she sets up the shop. Ray's teaching Frenchy in how to pick locks 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.
- 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.
- Fake-Real Turn: Again, the cookie shop.
- 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.
- 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".
- 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.