In Small Time Crooks, Ray (Woody Allen) concocts a plan to rob a bank. He wants to buy out a space neighboring the bank, then he and his wife and a small gang of fellow thieves will create a cookie store as the front while they tunnel into the bank.
It feels like an extended sketch show in which they fail repeatedly and in silly ways. First they dig into a pipe, and water floods the basement. Then they dig the wrong way and tunnel into a clothing store. Then, ultimately, the cookie store becomes wildly successful. The last one is a problem because Ray’s wife Frenchy (Tracey Ullman) can’t run the store by herself, but bringing in another set of hands means risking exposure to the bank robbery plan.
The risk is elevated when a police officer gets involved, but it turns out to be a good thing because he suggests they franchise the cookie store, and he wants in. So the story abandons the robbery idea, and we cut to a year later in which the franchise is running strong, and everyone’s rich.
The story then becomes about how Ray and Frenchy’s marriage is tested by wealth. Frenchy wants to fit in with the wealthy elite, including Hugh Grant, while Ray just wants to go back to his old life.
They briefly split up, but Frenchy is quickly dumped by Hugh Grant after he discovers her business has gone bankrupt (due to corrupt accountants). While that’s going on, Ray has returned to his thieving ways, trying to get a diamond necklace from a dinner party. Through a couple mishaps, he ends up with the fake necklace that was meant to be the decoy. He reunites with Frenchy, and they retire to Florida, with just enough money from a gift Frenchy bought for Hugh Grant but never gave to him.
Small Time Crooks is a comedy like Allen’s earliest films. The story goes wherever it wants to. Right when you think it’s going to be a heist film, it instead changes direction completely and becomes about characters assimilating into the upper class. Previous Woody Allen films have touched on the upper class world, but never so explicitly. In Manhattan, the characters love to talk about art and go to every museum opening, but they also don’t completely dress the part. Those characters probably wouldn’t think of themselves as being in the upper class. They’re too self-centered to see themselves as anything other than themselves.
In Small Time Crooks, however, the upper class knows they’re the upper class. They’re very aware of who’s in and who’s out, and Frenchy’s definitely out, though she desperately wants to be in. Hugh Grant indulges in her wealthy fantasies, educating her along the way, but he never means it. He only wants to take advantage of her. Grant is conniving in the same way Ray is. They’re both angling to steal something, but Grant does in under the disguise of his accent and lifestyle. Surely that type of person couldn’t be out to get you, right?
Ray is much more upfront about his intentions, though of course not with the people he’s targeting. He avoids people as much as possible when it comes to robbery. He snoops around and sneaks into safes whereas Hugh Grant milks his charm and looks Frenchy directly in the eye while he tries to undermine her.
Ray, though, is surprisingly genuine. He reminded me of Danny Rose in Broadway Danny Rose. Despite being a thief there’s something honest about him, probably because he knows what he wants. His thieving ways have some sort of end. He wants to live with Frenchy in Florida. It never feels too malicious, and that might just be because Ray is constantly failing, and he’s played by Woody Allen himself so there’s something disarming about Allen’s neurotic fast-talking. Actually, in the same way High Grant uses his charm to disarm Frenchy, Allen uses his familiar mannerisms to disarm the audience. Or does he? We always know what he’s up to, but we never care so much for the people he’s going after. He seems harmless, and he is harmless because he keeps failing. Maybe we just know he won’t succeed so it’s okay.
There’s something familiarly funny about someone trying to do something bad and then constantly messing up. There’s even an entire feature-length comedy about terrorists who keep messing up: Four Lions (2010).
So it’s okay to do something bad (in a movie) as long as you keep failing. At a certain point we begin to respect your drive or at least enjoy it knowing that it won’t hurt anyone. Another example is the guy who’s always trying to capture the Road Runner or Pinky and the Brain.
Maybe if we saw Ray succeed, we could get a better understanding of his character. Would he regret it?
We do get the sense that he can’t handle success when the cookie shop takes off. He’s someone who steals in order to maintain a simple life. The upper-class folk, though, would see their own thievery in the same light. Hugh Grant needs more money to extend his lifestyle and expand it because there’s pressure to keep up a certain image.
I have no idea what I’m saying anymore, I’m rambling.