The last time I saw Paul Giamatti in a lead role was in "Sideways" (2004), when he played a middle-aged guy who stole money from his aging mother to winery-hop in Napa Valley. Now Giamatti resembles a trusty musical instrument, fine-tuned to the exact specifications of what can only be described as Giamatti-ness. He's now 45 years old, but it feels like he's been playing that guy — the paunchy, balding, self-indulgent, easily wounded midlife crisis guy — forever. The tides will turn, the global climate will change, but Paul Giamatti is set in stone.
Though at times, even an actor such as Giamatti will get a version update, because in "Win Win," he's not just a 40-something loser looking for ways to cuddle his fragile ego. In keeping with the times, Giamatti's character Mike Flaherty is less obsessed with himself as how to pay the mortgage and keep his family of four fed, clothed and happy, all at the same time. Mike is a middling elder-care lawyer, permanently strapped for cash and keeping his financial woes secret from his improbably hot wife, Jackie (Amy Ryan), and their two young daughters. But the strain is starting to tear a hole in his gut. Plus, his moonlighting job adds to the agony: Mike coaches for the local New Jersey high school wrestling team and they're so bad it's not even funny.
And then Mike makes a wilful ethical slip at a court proceeding that basically amounts to swindling his client Leo (Burt Young, best known for playing Rocky's brother-in-law, Paulie), who is beset with Alzheimer's and refusing to move out of his home. If all goes well, it could mean a monthly windfall of an extra 1,500 bucks for Mike's household. If it doesn't, Mike could very well lose his practice. That bit of wrong-doing drops a ton of guilt on Mike's already considerable pile of personal stress.