When we first meet up with the hapless hero of "The Winning Season," Bill Greaves (Sam Rockwell), he’s busing tables at a T.G.I. Friday’s-like establishment and drinking himself into a stupor. An old friend (Rob Corddry) and current high school principal shows up to make an inexplicable offer for Greaves to become coach of the girls' basketball team (inexplicable because Greaves gives no indication that he’s either interested or in enough possession of his faculties enough to handle the job).
Greaves lived and breathed basketball for most of his life, but after a very public meltdown while coaching a boys' team, he retreated into a bottle and a dead-end job. His wife left him and he shares custody with a daughter that is boiling over with teen angst and resentment. After first thumbing his nose at the idea of coaching a bunch of girls, Greaves realizes it might be just the opportunity he needs to turn his life around.
To praise Sam Rockwell’s performance in any role at this point feels redundant. He’s one of the best actors of his generation; his inclusion in any cast bolsters even the least interesting flick. "The Winning Season" is certainly not that, but it isn’t a particularly great film, either. It has a strong start and a terrific ending with occasional winning moments in between, but the uneven story is heavily hindered by about 45 minutes smack in the middle of its 98-minute running time that feel forced, aimless and often redundant.
Writer/Director James C. Strouse ("Grace is Gone") never seems quite sure what he’s trying to do and say with 'The Winning Season." Rockwell’s Greaves is a broken character, but in order for us to root for his redemption, it’s important to feel he’s worthy, which grows difficult as the plot plods along. The film wanders intermittently into a few other disconnected and incomplete story lines - the lesbian bus driver-turned assistant coach dealing with acceptance in a close-minded small town; the player (future "Girl with the Dragon Tattoo" Rooney Mara is strong in the small part) dating a much-too-old deadbeat; the sexually confused daughter of the principal. Emma Roberts ("Nancy Drew") and Shareeka Eps ("Half Nelson") also play nicely off Rockwell as members of his team.
The issues that are related to the central storyline, such as Greaves' alcoholism (it can only play as a joke for so long), his daughter’s issues with him and the mysterious past incidents take far too long to unfold and still aren’t clear as we head into the third act. We don’t really know a lot about the character coming in and there are still questions late in the film. While it isn’t always necessary to reveal a character’s entire life story in the opening frames, it is a bit confounding in a story so rooted in past events.
"The Winning Season" teeters hither and thither on its tonal seesaw, never quite sure where it’s going and often forgetful of where it’s been. As Greaves faces down one missed opportunity after another and constantly shits on those who try to help him, it grows difficult to watch, much less cheer for, this shiftless antihero. Sure, there may be a level of sad realism to Greaves’ on-the-wagon, off-the-wagon struggle with drinking and emotional immaturity, but it often feels out of place in this otherwise lighthearted effort.