Writer/director Thomas McCarthy has made a name for himself through the delivery of rich characterizations, using formulaic plots to help establish the mood while developing three-dimensional personalities set loose inside a turbulent event of emotions. "Win Win" is generally more of the same from the filmmaker, though it suffers from a lopsided execution, struggling to stabilize dramatic footing with this fascinating group of lost souls. It's a pleasant film with marvelous performances, but it loses a great deal of stamina in the second half once McCarthy succumbs to predictability.

An attorney struggling to makes ends meet, Mike (Paul Giamatti) is losing his battle with stress, looking to keep his wife Jackie (Amy Ryan) calm and deal with his job as coach of the local high school wrestling team. When an opportunity to make a quick buck finds him the guardian of senior citizen Leo (Burt Young), Mike unknowingly steps into the middle of a tricky custody arrangement, a problem further exacerbated by the arrival of Kyle (Alex Shaffer), Leo's withdrawn teen grandson. Discovering the boy has a gift for wrestling, Mike makes him a part of the team, allowing Kyle a chance to rediscover the discipline he craves and the domestic stability he never enjoyed with his estranged addict mother (Melanie Lynskey).

In McCarthy's favor is a great deal of sincerity, from his chilly New York locations to the authenticity of discomfort churning within Mike as he falls deeper into dishonesty. It's a filmmaking quality that's rare to find these days, and "Win Win" benefits from a lived-in feel that helps to appreciate the characters and their fears, losing the mechanical push of development for the most part to keep tight to the actors and their incredible conviction to depicting uncertainty.

The first half of the film is devoted to establishing Mike's quicksand arrangement with Leo and his budding relationship with Kyle, setting the foundation of motivation while playing around with the tenets of underdog cinema as the boy is revealed to be a wrestling wonder. McCarthy is great with these establishing moments, constructing the mindset of the conflicted group while maintaining the machine of Mike's domestic duties, with Giamatti sharing outstanding chemistry with Ryan, who gives the traditional wife role a warmly confrontational spin (she's a Jersey girl after all, complete with a Jon Bon Jovi tattoo). When McCarthy allows his cast to interact, "Win Win" strikes a potent human note of discovery, exploring Kyle's anger issues and Mike's determination to protect all these strangers in his life. Giamatti nails the unsettled carriage of Mike, playing quiet moments of realization spectacularly. Newcomer Shaffer is wisely downplayed by McCarthy, kept to blunt answers and minimal physical communication, reflecting a genuine teenager. I haven't seen one of those on-screen in quite some time.

The second half of "Win Win" goes dramatic after a rather euphoric set-up, though the deceleration isn't the problem. McCarthy soon trots out conventional entanglements for Mike and Kyle that drag the story to a stop, electing familiarity over a more enriching plan of conflict for the makeshift family. The film loses balance quickly, moving from an animated sports film to a dull custody drama, without needed downshifting to allow the audience a chance to process the change of scenery. "Win Win" is a charming film, but loses focus when it strains to retain insight, artificially bottoming out the characters so their final reel reunion will mean something. There are already profound feelings in play without underlining, with the grind of convention squeezing the life out of an endearing film.