Two for the Money (R, 2005)

In TWO FOR THE MONEY, Al Pacino plays Walter, an aging mentor to a young, able, arrogant rookie. His student is Brandon (Matthew McConaughey), onetime sports devotee (baseball as a child, football as a teen and college student) who never recovers from a devastating injury during a big college game. And so he's working in a cubicle, answering 900-number lines and feeling bored. Brandon thus welcomes what appears to be his rescue by Walter, who gets wind of Brandon's remarkably good percentage in picking winners for sporting events. He moves to New York and into Walter's building, where he spends all his time working out and doing his sports homework, picking winners for clients at an astounding rate. Rechristened "John Anthony," he adopts a new persona, with slicked-back haircut and designer suits, and, painfully naive rube that he is, believes that the pretty girl (Jaime King) Walter purchases for him one evening actually "likes" him. But Walter's got all kinds of ulterior motives, none especially disguised, except, it seems, to Brandon. For one thing, he's a former gambler-addict-mess himself, now seeming to focus his energies on his six-year-old daughter and recovering junkie/beauty salon owner wife Toni (Rene Russo).

Though Toni believes that "Walter's held together by meetings," the film reveals otherwise, in part by making its smartest point -- not gambling on gambling is still gambling. That is, while Walter and Brandon and their fellow handicappers all talk big about not actually gambling, only picking winners for clients and drawing money from their winnings, in fact, it's all gambling. While Toni's untold story hints at intriguing complications (how did she meet Walter and why is she devoted to him?), Brandon's saga is as boring as can be. He gets cocky, he overreaches, he falls (during one especially yucky punishment scene, a client [Armand Assante] finds him in Central Park and has a thug hold him down so the client can urinate all over him). Eventually, Brandon finds his way back to himself, that is, Brandon rather than "John Anthony" (again, his faith in a real self that might be lost and found is rather quaint). Walter's story is much more compelling, because he does, at some level, get what gambling is about.

At one point during his lessons for Brandon, he drags the student and Toni into a Gamblers' Anonymous meeting and begins, by way of a speech about his long-term sobriety and his earnest understanding of the group members' complaints, explains that they're addicted to losing, then invites them to use his service, in order to be winners. "Gambling's not the problem. We're the problem," he rasps, "We're lemons. We're addicted to losing." It's something of an ingenious speech, ebbing and flowing, and Pacino chews it up as you might expect. It's a lie, too, which is the underlying point of Two for the Money. Losing or winning is not what's at issue in gambling. Rather, it's the potential that can be experienced only in the pre-conclusion moments. And here it becomes clear that Toni is the major stake for the two boys.