DVD Release Date: August 23, 2011
Theatrical Release Date: March 18, 2011 (limited)
Rating: R (for strong language)
Genre: Comedy-Drama
Run Time: 106 min.
Director: Jonathan Liebesman
Cast: Paul Giamatti, Amy Ryan, Bobby Cannavale, Alex Shaffer, Jeffrey Tambor, Burt Young, Melanie Lynskey, Margo Martindale

Win Win is an emotionally engaging slice-of-life dramedy about compromises and sacrifices, and how the former can, well, compromise the latter despite good motives. 

It’s also the kind of smart crowd-pleaser that major studios were making a generation ago, but today it’s a low-budget indie. On one hand that’s a shame, but on the other we’re lucky that this little charmer had the independence to preserve its integrity even while appealing to a wide mature audience.

Mike Flaherty (Paul Giamatti, Duplicity) is a small-claims attorney who moonlights as a high school wrestling coach. He’s compassionate at his job, committed to his team, but struggling with both. He tries to carry the burden alone as much as he can, keeping both his wife and employees in the dark about escalating financial straits while still maintaining his dedication to his wrestlers. He’s a good man with a big heart who wants to provide—both as a husband/father and mentor—but something’s gotta give.

Or does it? An opportunity presents itself to pull in substantial extra money with little effort, although it requires both a moral and legal compromise. The temptation is too great (and the window to take it too short), so Mike gives in with the best intentions—but if he’s caught, he could lose his practice. This looming Sword of Damocles makes an already-worrisome Mike even more anxious, resulting in brief smoking relapses and intense panic attacks.

Complicating matters even more is that this decision leads to Mike and his wife Jackie becoming custodians of the teenage runaway grandson of one of Mike’s clients. What at first appears temporary becomes more complicated, emotionally and relationally, as the kid is a stand-out wrestler from another state who could end up helping Mike’s team. Yet for as genuine a bond as they form, Mike’s sincerity toward this neglected young man could be seen as self-serving and manipulative if Mike’s secret is ever revealed.

All of this sounds very weighty—and indeed, it’s taken seriously—but Win Win is a comedy, often taking a light approach to its subject without ever taking lightly its themes or moral layers. More specifically, while the circumstances are played straight, the humor is found in the characters’ oddities and anxieties. 

This isn’t situational comedy; it’s human comedy. The former only strives for laughs. The latter aspires to reveal things about ourselves: the good, the bad, the gray, and in the case of Win Win that moral compromises can never be trusted even when they’re made with genuinely selfless objectives in mind. In the end, you risk losing all of the people you were trying to save.

It takes a deft directorial touch to blend reality and comedy without diluting either, something writer/director Tom McCarthy has displayed in previous award-winning festival favorites The Station Agent and the more-serious The Visitor. This proves to be a funnier and more mainstream effort, but one that maintains an honest and subtle tone. McCarthy’s screenplay is a model of structure, character, wit and depth, and his perfectly calibrated direction feels simple and effortless (which means it was anything but).