How is a family made? And what makes it a family anyway? Sometimes the answers aren’t what we might expect, and Win Win presents just such a situation. It manages to be heartwarming and sweet while remaining wryly funny and avoiding the syrupy depths these films are so often prone to.
Mike Flaherty (Paul Giamatti) is a man in crisis. He supports a wife, Jackie (Amy Ryan), and two young daughters in New Providence, New Jersey; his law practice isn’t going much of anywhere; the ancient boiler in the basement of the house where his practice shares space with that of his CPA friend Stephen (Jeffrey Tambor) is about to explode. Mike has a panic attack while jogging with his high school friend Terry (Bobby Cannavale) — one of several, for which his doctor has prescribed jogging. He’s the coach of his old high school wrestling team, which is abysmal. Mike is the picture of quiet desperation.
But there emerges a ray of hope. Mike has been appointed as counsel to Leo (Burt Young), an elderly man on the cusp of senility. Leo wants to remain living at home, but without any family to be found, he’s about to be declared unfit and a ward of the state. But Mike realizes that Leo is pretty well loaded; he can assume guardianship, place Leo into a retirement home, and collect a sizable stipend for his troubles.
Unfortunately, it’s not that simple. Leo’s teenaged grandson Kyle (Alex Shaffer) turns up on the doorstep of Leo’s vacant house. His mother Cindy (Melanie Lynsky) — Leo’s estranged daughter — is in a rehab program, and her boyfriend evidently doesn’t treat Kyle very well. Unsure what else to do, Mike and Jackie take him in for the time being.
Now, Kyle’s situation could easily provide the excuse for some epic histrionics, but writer/director Thomas McCarthy’s story is smarter than that. Kyle has some issues, sure — he’s made some mistakes and he has a tendency to be withdrawn and introspective — but at heart he’s a good kid. Mike enrolls him in the high school when he finds out that Kyle is actually a phenomenal wrestler. And despite some early misgivings Jackie’s mothering instinct quickly takes hold, and Kyle blossoms in a truly caring environment for the first time.
What emerges is a portrait of a family determined more by the whims of chance and the bonds of affection than by the mere facts of biology. It’s a place of mutual support and encouragement, where people make mistakes but are also given second chances. It’s the sort of environment all of us wish for.
Giamatti is, of course, excellent. Ryan is absolutely charming, pulling a real character out of what could easily have been a stereotype. Cannavale, Tambor, and Young are all wonderfully comedic leaveners, each in their own ways. And Clare Foley is adorable as the older of Mike’s daughters.
But Shaffer may be the real gem here. With a single credit to his name, it may well be that he is basically just playing a version of himself, but that’s not the sense I get. Kyle may be the single most realistic teenaged character I’ve seen in any movie, and I just don’t see that happening by chance. He has depth and nuance far beyond simply being “troubled”. We sense layers beneath his curt responses that take real skill to portray this effectively.
As a whole, Win Win is a truly moving picture. It balances its sweetness with enough of a bite to keep it from getting sappy or maudlin. It feels very true, avoiding the easier, more well-traveled narrative pathways that end up ringing hollow. And it’s genuinely funny in a way that builds up the characters and the audience alike.
Worth It: definitely.
Bechdel Test: fail.