Boiler Room (2000) is the youth-appeal version of Oliver Stone's Wall Street (1987). Giovanni Ribisi plays nineteen year old Seth Davis who has dropped out of college to run a gambling club out of his college apartment. His father, a judge, learns of it, & rails against his son's morally suspicious behavior.
The one thing Seth wants more than money is his father's approval which has always been withheld. So he tries to find an honest job, though alas he slowly realizes he has become a stock broker not in a legitimate firm, but in a "chop shop" consisting of little more than fast-talkers & phone banks for bilking the public.
When word gets back to his dad that his son no longer runs an honest amateur casino, he's glad of that; but when it turns out he's instead become a thief in a phony stock brokerage, dad wants to disown Seth entirely.
Ben Affleck, an actor I've rarely liked on the screen, is somehow great as the handsome well-dressed dirty rotten fiendish shithead coach of the trainees in the criminal brokerage. I can rarely buy into Affleck as a heroic leading man, but as a secondary villain, he was born to play that well.
Boiler Room provides a convincingly cynical view of life behind the scenes at the lower end of stock brokering. Seth is a semi-honest sort of guy who ran his illegal casino with integrity. He easily becomes guilt-ridden when he realizes he has been stealing peoples' life savings & destroying lives.
But Chris Varick (Vin Diesel) is a big-brother figure at the firm. He seems to care about Seth & counsels him to never question the system. Seth tries to buy into the idea that if he pretends not to know what's going on, then he's not doing anything wrong.
He's additionally dating Abbie (Nia Long) who likewise doesn't want the boat rocked since she relies on her overpaid secretarial position to support her extremely ill mother.
There are a lot of forces encouraging him to go with the flow. But the more he learns, the more he dislikes the firm & what it has turned him into. While trying to out-scheme the schemers, he drags his father into the mess immediately before the Feds close in.
Seth agrees to turn state's witness & retrieve for them the best evidence they'll ever see, but only if his father is allowed to walk out of the room with his judgeship intact. Otherwise he'd rather go to jail.
In a persistently cynical film, Seth's patient if sometimes badly planned quest for his father's affection provides the film's biggest moments of humanity. This subplot takes the meanness off the edge of the rest of the tale.
By the end, Seth no longer wants to gain anything for himself. He wants to take the firm down but warns his one friend Chris about the raid. And he wants to abscond with enough of the firm's loot that he can return the lost life savings of a guy who is losing his family thanks to Seth. After that, himself flat busted but in the clear, he wants to find a job that will do his father proud.
The film is slight & somewhat monotone. But Ribisi is such a fine actor. The success of the film rides on his shoulders. Boiler Room fortunately remains a film of character & never descends into Hollywood style heist & car-chase & shoot-out, in spite of a somewhat gangstery cast that couldn't gone that direction.
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