It's uncommon to find comedic dramas that balance themselves out so decently, mixing both genres that can create an entertaining ride. The main attraction here is Paul Giamatti, but the rest of the cast does a good job bringing along characters with a clearly defined role: comedy, irony, drama, tenderness, etc.
Thomas McCarthy was born as an independent director, but since The Station Agent (2003), he seems to have become another average and forgettable Hollywood name despite the interesting proposals of emotional downfalls and complex dilemmas that his characters had presented. He seems to present the same array of characters to balance everything. In this case, such balance is present again (sorry for being reiterative) but the film offers nothing entirely original for considering Win Win as a refreshing proposal, and the resolution, despite being quite fair and reasonable, rushes things fot a proper powerful closure.
Still, it's worth a watch.