It’s a win-win situation. You’re a lawyer. Not the kind with a McMansion besieged by your contractor-boinking ex like you’re childhood chum Terry (Bobby Cannavale). The kind who represents elderly gentlemen with stolen cat cases and has an office in an old house with a chiming boiler that’s about to blow. And Leo (Burt Young), a client with a lopsided grin and the adorable innocence of early dementia. So adorable you want to take him home with you, or adopt him, or -- better yet -- take his money (which he has plenty of) and deposit him at a fancy old folks facility and deposit the $1,500 a month you get for being his legal guardian (and pretending to care for him in his home) to your dwindling bank account. But no need to feel too bad about it, since before long he won’t know or care where or who he is. Or so Mike Flaherty (Paul Giamatti) rationalizes in writer/director Tom McCarthy’s (Up, The Visitor) newest indie flick Win Win.
It’s a nice movie. Even when it does bad things, it’s hard to stay mad at it -- much like Mike and the rest of its characters. Like them, the film is also sincere, soft-spoken, honest, and thoughtful. It runs on the everyday drama of family, relationships, and good people in tough situations who make morally iffy decisions.
When Leo’s grandson Kyle -- fed up with Ohio and his drug-addict mother, Cindy (Two and a Half Men's Melanie Lynskey) -- shows up on his doorstep, Mike worries that his win-win arrangement may be over. Then he discovers Kyle’s a wrestling prodigy. This is great news as Mike happens to moonlight as a high school wrestling coach. Now it’s a win-win-win situation after he takes Kyle into his home and recruits him for his lose-lose wrestling team. (It’s also an added perk for sports fans in the audience who can revel in rooting for the budding wrestling champ.) All’s well until Cindy shows up, fresh out of rehab and itching to get Leo’s money.
Poor Paulie, er Leo -- how could anyone steal from such a seemingly sweet old man? Rocky Balboa’s former coach disarmingly portrays the not-all-there object of everyone’s greed. Giamatti is also as sympathetic and genuine as you’d expect as the compassionate, internally torn lawyer, coach, and family man. Terry and fellow coach Stephen (Arrested Development’s Jeffery Tambor) fuel the film’s goodhearted sense of humor. But the star of Win Win is the same head-locking talent that every high school wrestler and coach wants to be. Wavy bleach-blond locks, an aquiline nose -- newcomer Alex Shaffer recalls a young Sean Penn with Ridgemont High hair and something approaching Thin Red Line depth. As Kyle, he’s a man-boy of few words and profound silences, tattooed, sullen sometimes, but mostly enigmatically cool and surprisingly well-mannered despite his dysfunctional roots. It’s like June Cleaver and Billy Idol had a son.
An honest, insightful, and funny feel-good film that doesn’t toot (or, like most feel-good films, blast) its own horn and life-affirming message: if that’s your notion of a good day at the movies, then Win Win should be a win for you.