The first 15 minutes of Win Win are bumpy. It starts out with that familiar whimsical Indie movie music that signals we’re about to meet a bunch of intentionally quirky White people who mean well in spite of the fact that they’re socially awkward and have trouble connecting. To drive home the point, the king of Wonder Bread angst Paul Giamatti is present and accounted for as Mike Flaherty, a struggling lawyer.
The cutesy music soon fades away though and the story’s choppy beginning is quickly forgotten as the characters begin to emerge as real people. Mike, a family man with two kids and an opinionated but loving wife Jackie played by Amy Ryan, is on the verge of losing his law practice. When a client Leo Poplar (Burt Young) suffering from dementia comes to him for help he sees a way out of his financial dilemma that is not only unethical but doesn’t serve what’s in the best interest of Leo. Mike’s actions, of course, will come back to bite him later.
In his spare time, Mike is a high school wrestling coach to what may be the worst team anyone has ever seen. Helping him out as assistant coach is his buddy Stephen (Jeffrey Tambor). Scene-stealer Bobby Cannavale is Mike’s best friend Terry who is obsessed with following his cheating and soon to be ex-wife. Yes, Cannavale can make stalking your ex seem simultaneously harmless, hilarious and all too familiar. The hyper Terry forces his way in as a volunteer coach on Mike’s team to get his mind off his divorce.
Life becomes even more complicated for Mike and his family when Leo’s teenage grandson Kyle (Alex Shaffer) unexpectedly shows up for a visit and decides to stick around. Jackie insists that Kyle stay with them when she learns his mother is in drug rehab. Before long Kyle joins the wrestling team and Mike discovers that he’s a talented athlete with a chance at a scholarship and the ability to help him transform his team of misfits. With Kyle on board the team slowly begins to take shape and surrounded by a loving family the detached, alienated Kyle slowly opens up.
The pretty picture doesn’t last for long. The sudden appearance of Leo’s long lost daughter, Kyle’s mother Cindy (Melanie Lynskey) threatens to expose Mike’s dishonesty and sends Kyle into a tailspin.
The cast gels together to form a group of people you come to believe do exist. Alex Schaffer manages to make Leo withdrawn yet conveys the teen’s emotion and strong will underneath the surface. Burt Young portrays Leo as a man suffering from dementia who still knows what he wants and certainly more than he lets on. Amy Ryan turns Jackie’s desire to punch anyone who has wronged the people she cares about into an endearing quality.
Win Win turns out to have that same quality without the forced preciousness that is a mark of too many of these indie type family movies.