David Rooney, THR:
"It's no surprise that McCarthy is a skilled actor's director, but the heartfelt compassion and observational acuity that infuses the writer-director's films is what distinguishes them most. In all three features, he has shown a rare ability to shape unexpected connections between very real people, guiding them toward gently uplifting outcomes that are neither manipulative nor sentimental. That might make him one of the least cynical filmmakers working in America…McCarthy's screenplay never strikes a false note…newcomer Shaffer is genuinely moving as a good-hearted, damaged kid and a motivated sportsman who is the antithesis of the standard-issue screen teen jock. It's as much his movie as Giamatti's, though Mike's understated sweetness and the melancholy pragmatism with which he faces up to his transgression make this arguably the actor's best role since Sideways."
Pam Grady, Box Office Magazine:
"Win Win is a film with a big heart; it's an eccentric dramedy and a crowd pleaser…It's to Giamatti's credit as an actor (and McCarthy's as a writer) that we have an unerring feel for the soft center in Mike; even as he's behaving badly we sympathize with him…The entire cast is great, with the ebullient Cannavale a standout, but the real find here is Shaffer in his first movie…With witty and believable dialogue, a situation that's both funny and sad, and a group of actors that sink into their roles, this is McCarthy's best film yet. Once again, he proves that he is a writer with a grasp of character and story, a warm-hearted, generous chronicler of human connection. With his latest, he certainly got the title right. It really is a Win Win."
Chris Bumbray, JoBlo:
"In many ways, Win Winfeels like a less schmaltzy and cloying version of The Blind Side. It's certainly a more authentically moving film, as this contains actual characters and not caricatures. This is a great change of pace for Paul Giamatti, who tends to specialize in edgy roles, but is wonderful here as a struggling lawyer/coach, who's also an ideal father/husband, and can't help but take a troubled kid like Kyle under his wing. It's a moving, gem of a part for Giamatti, and I especially liked his chemistry with Amy Ryan, with the two of them making the screen's most ideal parents since Stanley Tucci and Patricia Clarkson in Easy A…it makes me upset to think that a real, quality family flick like WIN WIN is going to get slapped with an R- Rating, due to some swearing, which is not excessive, but rather feels truthful, and altogether necessary to the parts of the movie it`s featured in. If you've got kids, and you're looking for a solid family film, WIN WIN is really the film for you."
Jeff Sneider, TheWrap:
"The performances are truly excellent across the board. Giamatti and Ryan are both predictably fantastic, though it's McCarthy's go-to-guy Bobby Cannavale who steals the movie as Mike's best friend Terry, an unemployed hedge fund type whose wife has recently left him…Sheffer delivers an impressive debut with one of the most natural teen performances I've seen in some time. He has a complicated role to play that demands more from him as the movie goes on, and the rookie actor is more than up to the task of holding his own with Oscar nominees Giamatti and Ryan…Credit is due to the film's casting director, as fellow newcomer David Thompson (making his feature debut) also makes a memorable impression as one of Kyle's less-talented teammates."