Nestled between the insufferable The Station Agent (2003) and the immensely moving The Visitor (2007), Thomas McCarthy’s third movie, Win Win, is luckily closer to the latter than the former in terms of quality. There’s a real earnestness to the proceedings: if someone had relayed the setup to me via email or over cocktails, I would have bet heavily that we’d be looking at a sappy mess of clichés. To my delight, McCarthy continues to display an evolving delicacy (my primary, and major, issue with The Station Agent was its complete lack of subtlety, and how it hammered its viewers over the head with its point on a regular basis), managing to avoid portraying Win Win‘s characters as caricatures. The premise: beleaguered attorney Mike Flaherty (Paul Giamatti), who doubles as a wrestling coach at the local high school, has a faltering legal practice—he can’t afford an IT guy, or even a new boiler—and his personal finances are becoming shakier and shakier. Through a legal loophole, he appoints himself guardian of his elderly, wealthy client Leo (Burt Young), and shuttles him off to a nearby old-age home, thereby avoiding the responsibility of guardianship while pocketing the $1,500-a-month commission. But things get hairy when Leo’s grandson Kyle (Alex Shaffer) shows up at his doorstep, having run away from his alcoholic mother Cindy (Melanie Lynskey) in Ohio, and Mike has to balance his careers, moral hazards, and a developing fondness for the quiet-but-supremely-talented Kyle.

McCarthy deftly keeps things from spiraling into the predictable or hokey. For instance, despite Mike’s conniving move, he never comes across as a particularly slimy guy. In fact, if we didn’t know that he’d played the court, we wouldn’t think much was wrong with him at all. He visits Leo regularly, grows to care for Kyle deeply, and wants the best for his family. Of course, there’s certainly some opportunistic behavior going on—when Mike discovers that Kyle used to be a top-ranked wrestler in Ohio, it takes him about two seconds to pounce—but his emotions and actions always seem authentic. This is a man who’s scared, and if he can find a way to help the ones he loves without seriously affecting someone else, he’s willing to do it. Similar analyses apply to Kyle’s evolution as a character, and even those of Mike’s down-to-earth wife Jackie (Amy Ryan) and his recently-divorced, lost-in-life best friend Terry (Bobby Cannavale). All have personality traits that seemingly lend themselves to hokum, but they all manage to transcend that and come  across as totally believable. The acting certainly helps matters: while there’s not a mind-blowing performance in the bunch, Giamatti, Young & co. all turn in stellar work.

So what holds Win Win back from being a great film? Well, first and foremost, it lacks the emotional heft of The Visitor. While McCarthy shows the same compassion for those that society has discarded as he did in his previous works—little people in The Station Agent; illegal immigrants in The Visitor; emotionally abandoned child in Win Win—he’s unable to deeply tap into our reservoir of feelings here. There’s a workmanlike feeling throughout Win Win, one that’s effective and unsentimental, but never ultimately rewarding. The final 20 minutes or so also aren’t on the same level as the rest of the picture: they feel slightly more scripted and less authentic. That’s a shame, because it saps a lot of the momentum that Win Win had built up throughout. Flaws aside, there’s a lot to like about Win Win, and McCarthy’s approach and sensitivity should serve him well as he continues to evolve as a filmmaker.

65/100