Luck (2003)

1972. Canadian Shane Bradley is an aspiring writer who instead is working a dead end job writing item descriptions for a furniture catalog. His three best friends are: Andrew, who he's known since high school, a former concert pianist who now works as a pit boss in a casino; his roommate Vittorio, a chronic worrier; and Iranian Robbie, who is always pulling some scam and seemingly not worrying too much about the results or consequences. Three things happen concurrently in Shane's life. First, he is as consumed by the Canada-Russia summit series as any proud Canadian, he who didn't even know the Soviets played hockey before the series started. Second, he believes he now has a chance with Margaret, a woman he's been friends with for four years since college and who he has been madly in love with the entire time. His belief in having that chance with her is finding out she and her boyfriend Justin have broken up, and Margaret planting a spontaneous kiss on him. And third, he becomes addicted to gambling, he not even interested in gambling before the start of the first two items, unlike especially Andrew and Robbie who are always at the track. These three items quickly start falling apart. Half way through the hockey series, the Canadians are far behind. Margaret's off again relationship with Justin is possibly on again as she asks Shane to feed her cat while she and Justin are away in England on vacation. And Shane's gambling problem gets him deep into debt, ultimately with a loan shark named Bill. Regardless of if the three items or their simultaneous decline are at all connected (Shane believing they being so), Shane, with Andrew, Vittorio and Robbie by his side, force at least two of those items together as Shane does whatever he can to raise the money to pay back Bill, the consequences for not being severe. Through it all, Shane, for once in his life, wants to win, breaking even not an acceptable option.