Win Win is a Win Win

Imagine my frustration. The whole point of this blog is to point an accusing finger at the sorry state of movie-making, to take out, as it were, the Hollywood trash. The along comes Win Win, a disarming and truly funny comedy. It’s a small movie, which is one of its charms, a movie clearly made for a price, and yet it surprises you at every turn.

Mike Flaherty is a down-on-his-luck lawyer who seizes an opportunity without thinking it through, an opportunity that turns into a nightmare. He takes on the care of an elderly man who’s in the early stages of dementia. And if that’s not bad enough, soon the old man’s grandson and later his daughter show up. Have you ever seen a plate-spinner in the circus or on the old Ed Sullivan show? You know, the guy who spins twenty or more plates on the ends of twenty or more wands, racing back and forth to keep them all spinning. Win Win is like that as Mike struggles to keep his bad deed from destroying everything that matters to him.

Paul Giamatti, the Indie scene’s everyman, plays Mike as a combination of loyal family man, dedicated wrestling coach, and desperate schemer. What is that trick Giamatti does with his eyes? The rest of his face may exude charm and innocence while his eyes, without even moving, convey his anxiety about being caught in a lie.

And Amy Ryan, who tore up the screen in Gone Baby, Gone, is the most fully formed female character I’ve seen in many a movie. She loves her husband, but she’ll call him on his crap when she has to. Two of our best actors, Giamatti and Ryan know how to play several shades of feeling, even contradictory shades, at the same time. Poet John Keats called it “negative capability”–“being in uncertainties, Mysteries, doubts without any irritable reaching after fact & reason.” It’s what we see in performances by DeNiro, Streep, Pacino, Denzel Washington, Ryan Gosling, Viola Davis, and only a handful of other actors.

Even young Alex Shaffer, who plays Kyle, does a stand-out job as the troubled teen who hides his pain behind a veil of insolence, indifference, and mystery.

And I can’t help mentioning one of my favorite actors, Margo Martindale, who plays Kyle’s mother’s lawyer. It’s a tiny part, but the measure of Martindale’s talent is how completely realized the character is. If you want to see what this talented actor can do with a larger canvas, watch this season’s episodes of Justified, where she plays Mags Bennett, the ruthless matriarch of a clan of redneck evildoers.

Bobby Cannavale, as Mike’s impulsive but well-intentioned friend, has the best role of his career and runs away with it. The ubiquitous Jeffrey Tambor gives the movie its deadpan anchor. We’ve seen him play over-the-top lunatics like Hank Kingsley on The Larry Sanders Show. Here he plays Stephen Vigman just this side of the line between the real and the ridiculous. You laugh at him not because he’s ridiculous but because he’s so like us. Melanie Lynskey, who for years has added a touch of surreal humor to Two and a Half Men, plays Kyle’s drug-addicted mother. It’s a measure of her talent that she can make you dislike her and feel sorry for her at the same time.

The humor in Win Win arises out of character, out of the breakdown between how we picture the world and how it really is. The screenwriter strikes this note from the very beginning. Mike’s daughter asks her mother, “Where’s Daddy?” “He’s running,” she replies. “From what?” his daughter says. This brief exchange establishes Mike’s character, the movie’s theme, and the kind of humor that runs throughout. Win Win’s got more laughs per square inch than Arthur or any other so-called comedy of recent memory.

Win Win is about old-fashioned things like honor and sacrifice and second chances, about doing the right thing even after you’ve done the wrong thing. And somehow it touches on all this without being sententious and while making us laugh. At one point, when one of his spectacularly untalented wrestlers finishes his match without being pinned by his opponent, Mike points out that sometimes not losing is the biggest victory you can win. It’s a painful yet reassuring truth like this that makes this movie matter.


Author: Brent Spencer

I'm a writer of fiction, creative non-fiction, and screenplays. My most recent book, a memoir, is Rattlesnake Daddy: A Son's Search for His Father. I live on an acreage in eastern Nebraska and teach creative writing at Creighton University. You can find out more about me and at (Photo credit: Miriam Berkley)

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