Win Win

The funny and poignant Win Win is best enjoyed with minimal information going into it, allowing the story to unfold with its dramatic and humorous exchanges intact. The trailer gives away too many second-half developments for a movie that could be described as an R-rated version of The Blind Side.

Don’t read too much into that comparison, though: The Blind Side was based on a true story; this one is pure fiction. The Blind Side was wholesome; Win Win has a fair amount of profanity and lacks overt Christian undertones (though the core family in the film is seen going to church). But both films share a heartwarming mixture of drama and comedy, depicting families whose lives are enriched after loving troubled teens with hidden talents.

Paul Giamatti—always terrific at playing the down-on-his-luck everyman—gives one of his most charming and relatable performances as Mike Flaherty, a family man with two young children living in suburban New Jersey. He operates a struggling law firm while also coaching the high school wrestling team with his friend Vigman (perpetually dour Jeffrey Tambor). As the clients dwindle and the bills pile up, Mike suffers from stress attacks, trying to get healthier by faithfully jogging every morning; it’s not helping much.

A simple solution arises via one of Mike’s clients. The state wants to put elderly Leo (Burt Young from the Rocky movies) in a hospital since he is in the early stages of dementia with no immediate family in contact—his daughter in Ohio has been out of touch for 20 years. Drawn to the extra income that Leo can afford for personal care, Mike offers to serve as guardian so that Leo can rest comfortably at home. A seemingly noble gesture, except Mike isn’t entirely truthful to the judge (or his family) about the arrangement: he puts Leo in a local retirement home, checking on him just enough to get away with collecting the monthly paycheck.

With Mike’s financial burdens lightened and no one the wiser, everything seems to be fine … until Leo’s grandson Kyle (newcomer Alex Shaffer) shows up for an unexpected visit. Despite the reservations of Mike’s wife Jackie (Amy Ryan), they agree to let the quiet and troubled teen stay in their basement, and soon become more sympathetic after learning that Kyle’s mom is a drug addict back in Ohio. As they figure out what to do with the boy, Mike allows Kyle to tag along with him to work and wrestling practice, only to find out there’s more to Kyle than meets the eye.

Conveniently, Kyle and Mike turn out to be exactly what they need each other to be. Some might see that as a plot contrivance, but isn’t life filled with stories of happenstance and serendipity? It doesn’t feel contrived here; Win Win somehow makes its developments feel true to our own experiences.

Director and co-writer Thomas McCarthy (2007’s critically acclaimed The Visitor) has crafted a film with authenticity and heart. There are times where it teeters close to sitcom territory, but there’s enough weight to the moral dilemmas to elevate it. Even if it were a sitcom, it’d be one of TV’s best.

It also helps that the plotting is somewhat unpredictable. In the first thirty minutes, Win Win flirts with approximately six different genres/scenarios (e.g. the midlife crisis movie, the caring for the elderly movie) before it becomes more apparent where things are headed. That’s not to say the story goes to strange places or treads toward unfamiliar territory, but that it won’t settle for the most obvious route in getting there. For example, Mike does get to deliver the standard inspirational coach speech, but things don’t turn out quite as expected afterwards.

Grounding all of this are strong performances. Giamatti is always terrific, but it’s a pleasure to see him play a less smarmy, generally well-intentioned character faced with moral conflict. Ryan is one of today’s most underappreciated actresses; here she plays a believable and relatable parent (and only five months after giving birth in real life). Bobby Cannavale is a scene-stealer as Mike’s best friend Terry, a foul-mouthed but lovable man-child who says whatever is on his mind, no matter how inappropriate. Though he’s the primary reason for the R rating, it’s nice to see how his character grows throughout the story.

And special recognition for the spot-on portrayal of modern teenage boys. Too often the kids are portrayed as unrealistically smarter than the adults, or else turned into two-dimensional caricatures. As Kyle, Shaffer (who really is a high school wrestling champ) shows depth despite the monosyllabic and monotone delivery (more realism); plus it gives his character room to grow from indifference to passion as he finds something worth fighting for. Kyle’s sweetly dorky friend Stemler is also a joy to watch.

Win Win lives up to its title, championing virtue by presenting a realistic moral dilemma that shows consequences to wrong (selfishness) and right (sacrifice) in relationships. It shows how one (not entirely) unselfish act can start a chain reaction of good in the lives of other people. It’s the rare gem of a modern comedy that’s smart, touching, funny—and, like life, a little unpredictable.

Talk About It

Discussion starters

What do you make of Mike’s initial decision to become Leo’s guardian? Might he have planned it one way but then changed his mind at some point? What do you think would have been the right thing to do concerning Leo?
What about the situation with Kyle? Does Mike act selfishly concerning Kyle’s well-being or is he only concerned about his own success? Is Kyle better off for knowing Mike or is he a victim? Would you have handled their relationship any differently?
Where does Mike screw up in his efforts to do good? How does he ultimately redeem himself? Explain how he does what is easy instead of doing what is right.
How would you characterize Mike and Jackie’s marriage at the beginning of the film? How is it strained? How is it strengthened? What does this film teach us about the basis for a strong marriage—what to do and what not to do?
Give examples of how each character is strengthened by the actions of another. How is this movie an illustration of things working together for good despite our sinfulness (Romans 8:28)?

The Family Corner

Parents to Consider

Win Win is rated R for language, including misuse of God’s name and recurring f-bombs; even the first line of dialogue has a young girl using a bad word. There’s brief nudity when one character photographs his bare bottom to send on a cell phone. Characters are also shown smoking, including 16-year-old Kyle, but it’s consistently depicted as a bad habit.