Today: October 6, 2026

Win Win

Paul Giamatti is Hollywood’s go to man if you want a grumpy sad sack dealing with a mid-life crisis – Sideways, American Splendor, Barney’s Version – you name it, he’s been miserable in it.

Paul Giamatti is Hollywood’s go to man if you want a grumpy sad sack dealing with a mid-life crisis – Sideways, American Splendor, Barney’s Version – you name it, he’s been miserable in it. That’s fine, he’s good at what he does but it’s no surprise to find him playing a similar role in Win Win where he stars as struggling attorney and high school wrestling coach, Mike Flaherty.

Mike’s almost at breaking point. He’s happily married to his understanding if uncompromising wife Jackie (Amy Ryan), and he loves his two young children but his practice is on the rocks and he’s in desperate need of money. In his spare time, he coaches the high school wrestling team but they haven’t ever won a match. He shares his office with equally glum accountant Vig (perennial misery guts Jeffrey Tambor) who also helps out as assistant coach, and hangs out with Terry (the ever-likable Bobby Cannavale), a loudmouth still reeling from the aftermath of a bitter divorce.

The chance of a financial reprieve comes when he realises that he can get $1,500 a month if he signs up for the guardianship of one of his clients Leo (hey, it’s that guy! – Burt Young – yes, Rocky’s brother-in-law) who wants to live at home but is battling senility. After pocketing the money, Mike promptly double-crosses Leo and puts him in nursing home anyway. It’s a despicable act but Mike rationalises that the nursing home’s a good one and he really needs the money.

Predictably, Mike’s shiny apple cart is upset by the arrival of the peroxided and tattooed Kyle, Leo’s 16 year old grandson who’s run away from his recovering junkie mother with hopes of staying with his grandfather. Instead he moves in with Mike and his wife and surprise surprise turns out to be a high-school wrestling champion, who single-handed manages to turn the team’s favours.

As Mike’s original deception grows and the situation becomes even more complicated, it’s inevitable that the whole house of cards will come crashing down.

Amy Ryan and Paul Giamatti make an extremely convincing onscreen couple – years of history are implied in a single scene and they really do feel like they’re married with children; he’s weary, but she’s tolerant of his foibles – to a point. The supporting cast are equally good – Jeffrey Tambor in particular has a hang-dog expression to rival Giamatti’s, so much so that they appear to be runners up in a Droopy look-a-like competition when they’re on screen together. Bobby Carnavale also provides some comedy relief as competitive man-child Terry – living vicariously through Kyle wrestling victories.

Newcomer Alex Shaffer is surprisingly effective, even if he was hired more for his wrestling rather than his acting skills. Peroxided, tattooed and possessed of the monosyllabic grunting that some teenagers substitute for conversation, he’s actually extremely charming and oddly magnetic.

Win Win’s improbable situations are more the stuff of TV sitcom than big screen comedy but it’s effortlessly well-acted and frequently very funny and so it’s easy to forgive its rather too neat tie-up-all-the-threads ending. It also earns points for sidestepping the “dramatic sports cliché ending” by focusing on the inter-family dynamic instead of the competition – it would have completely fallen apart if it featured a Karate Kid-esque showdown.

It won’t send you running from the cinema with your t-shirt pulled over your head, but it’s an likable and good natured comedy. Well worth a look.

Marcia Degia - Publisher

Marcia Degia, who has worked in the media industry for more than 20 years, is the Publishing Editor of KOL Social Magazine. See website: thekolsocial.com

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