Film

Small Time Crooks

Name: Small Time Crooks
Genre: Comedy, Crime
Released: 2000
Cast: Woody Allen, Tracey Ullman, Michael Rapaport, Tony Darrow, Jon Lovitz

Woody Allen's lighthearted heist comedy about a small-time crook whose cookie shop front for a bank robbery becomes wildly profitable instead. It's a breezy, accessible Allen film—funny without pretension, interested in lovable failures and sudden wealth's awkwardness. For viewers who want crime caper charm without darkness or stakes.

TMDb rating

3.3

Should you watch it?

Watch it if you enjoy small-scale caper comedy where the schemers are more endearing than competent, and a dry, slightly shabby Woody Allen world is a pleasure in itself.

Skip it if you need sharp pacing and a steady run of gags, since its humor is loose, ambling and often content to let a scene sit without much urgency.

What it asks of you: Expect a brisk, easy ride of about ninety-four minutes with little to decode; settle into its low-key rhythm and enjoy small, deadpan awkwardness rather than waiting on big payoffs.

Not sure? Find tonight's pick in a minute.

If you liked this

Ocean's Eleven2001

A heist caper overflowing with charm, style, and an ensemble cast having genuine fun. Like Small Time Crooks, it prioritizes wit and likability over tension, making the crime almost secondary to the camaraderie.

But The plot is deliberately slight, and if you want real jeopardy or consequences, the breezy tone might feel evasive.

It's a Wonderful Life1946

Both films are warmly humanist stories about ordinary people in extraordinary circumstances, exploring what money means and whether it matters. Capra and Allen share an affection for the underdog.

But It's a Wonderful Life is deeply sentimental and runs three hours. If Small Time Crooks' lightness is what drew you, this emotional weight might feel oppressive.

The Wolf of Wall Street2013

A film about sudden, disorienting wealth and the absurdity of excess. Where Small Time Crooks finds the situation endearing, this finds it grotesque—same premise, opposite moral register.

But At nearly three hours and relentlessly loud and crude, it's the opposite of Small Time Crooks' gentle pacing. The nihilism might exhaust you.

Not sure tonight? Get a pick in a minute, starting from Small Time Crooks

The wildcard

Something you would not have found on your own.

A Fish Called Wanda1988

Both films trust that character and humor are enough to carry a crime plot; neither needs actual stakes or danger to be engaging.

A heist-comedy hybrid where the crime plot is genuine but secondary to character comedy. Like Small Time Crooks, the real story is about flawed people learning something about themselves through chaos.

But It's British and raucously sexual in ways that might feel dated. The animal cruelty running gag will disturb some viewers.

Raising Arizona1987

Coen Brothers comedy about criminals who are fundamentally decent and ill-suited to actual crime. The tone—funny, warm, chaotic—closely mirrors Small Time Crooks' sensibility.

But It's much weirder and more frenetic. The visual comedy is avant-garde by comparison, and the plot mechanics are less straightforward.

Local Hero1983

Bill Forsyth's film about an oil company representative sent to a Scottish village. Like Small Time Crooks, it's a comedy about ordinary people in unusual positions, full of gentle humor and heart.

But It moves slowly and requires patience with whimsy. If you want plot momentum, this is a meandering walk rather than a sprint.

Working Girl1988

A scrappy underdog story about ambition and class, with real warmth and humor. The sense of triumph through cleverness rather than virtue parallels Small Time Crooks' core appeal.

But It's a romantic comedy first and foremost, and the '80s corporate setting is very of its moment. The romance might feel saccharine if you're resistant.

Ghostbusters II1989

A comedy sequel that's earnest about its ensemble and genuinely funny without cynicism. It shares Small Time Crooks' willingness to be unpretentious and warmly absurd.

But It's a straight sequel to a cultural phenomenon, and if you haven't seen the original, this will feel like an in-joke. The spectacle is '80s heavy.

The Grand Budapest Hotel2014

Wes Anderson's jewel-box heist film, full of whimsy and visual delight. Like Allen's film, it treats crime as an occasion for charm rather than drama.

But Anderson's fastidious style is polarizing. If you prefer naturalism and don't love symmetry and pastel colors, the artifice will feel suffocating.

Paddington 22017

A film about kindness and goodwill solving problems that crime created. It shares Small Time Crooks' fundamental optimism about human nature and finds comedy in decency.

But It's a children's film, and if you watch exclusively adult content, it might feel saccharine or boring regardless of quality.

Ghostbusters: Afterlife2021

Both prioritize likable characters stumbling into success over plot momentum; both are structured around joy rather than conflict.

A comedy about people discovering they're unexpectedly good at something they never intended, and learning to work together. The warmth and heart—the genuine affection between characters—echoes Small Time Crooks perfectly.

But It's beholden to franchise nostalgia and IP; the emotional core struggles against the obligation to fan-service. Cynics will feel the machinery.

Yi Yi2000

Both films treat sudden or persistent wealth as a lens to examine what actually makes people happy—and both conclude the answer is simpler and messier than money.

Edward Yang's Taiwanese epic about a middle-class family navigating money, status, and happiness. It's funny, tender, and genuinely wise about whether wealth changes anything that matters. Made the same year as Small Time Crooks but from the opposite corner of the world.

But At 173 minutes, it's a commitment. It's patient and observational in ways that demand active attention; there's no plot machine carrying you forward.