Insomnia File #25: The Winning Season (dir by James C. Strouse)

Posted on May 10, 2017 by Lisa Marie Bowman

What’s an Insomnia File? You know how some times you just can’t get any sleep and, at about three in the morning, you’ll find yourself watching whatever you can find on cable? This feature is all about those insomnia-inspired discoveries!

If, last night, you were up at 11:45 then … well, you were probably like most people. To be honest, I don’t know if The Winning Season, which aired on Cinemax last night, really counts as an insomnia file. Being up at midnight probably doesn’t qualify as insomnia.

That said, The Winning Season is an extremely sweet and likable movie that, until I came across it last night, I had previously heard nothing about. Even if it wasn’t directly inspired by insomnia, this was a film that I was happy to discover and I’m going to recommend that, if you haven’t seen it, you discover it too.

Of course, I guess I shouldn’t be too shocked that I loved this film because it stars Sam Rockwell. Sam Rockwell is one of my favorite actors. It’s not just that he’s talented and that he frequently takes risks and chooses interesting projects, though all of that is certainly true. There’s a sincerity to Sam Rockwell’s performances. He’s one of those actors who, when you watch him, you feel as if he’s literally opening up his heart and soul to you. There are few actors who can make me cry quite as effectively as Sam Rockwell. That he didn’t win an Oscar for Moon (and has, in fact, never even been nominated) remains one of the most glaring mistakes in the history of the Academy Awards.

Sam Rockwell is at the center of The Winning Season and it’s hard to imagine the film working with anyone other than him in the leading role. Sam plays Bill, a former high school basketball star who is now a divorced alcoholic with a 16 year-old daughter that he struggles to communicate with. Like many of Rockwell’s character, Bill is irresponsible but he means well. Bill spends most of his time drinking and working as a busboy at a restaurant.

One night, Bill is approached by his former teammate, Terry (Rob Corddry). Terry is now a high school principal and he has an offer for Bill. Terry needs a new coach for the Girls’ Basketball Team. Even though Bill doesn’t consider Girls’ Basketball to be a real sport, he accepts the position.

And you can guess what happens. When Bill is first hired, no one takes the team seriously. There’s only six players on the team and none of them — not even the ones played by Emma Roberts and Rooney Mara — believe that they have a chance at a winning season. In fact, their best player breaks her ankle before the season even begins. After a rough start, Bill and the girls bond and soon, they start to win games.

Again, it’s not surprising but it is incredibly sweet. And, as predictable as it may be, the film still throws in a few unexpected twists. One thing that I liked is that, even after they started to get good, the team still struggled and lost the occasional game. They didn’t all magically become the best basketball players ever and, for that matter, Sam didn’t magically become the best coach in the world. This is an unapologetic crowd pleaser that still keeps one foot in reality. Everyone, in the film, fully commits to their roles. In particular, Margo Martindale is great in the role of Bill’s assistant. It’s always a pleasure to watch two good actors play off of each other and Martindale’s scenes with Sam Rockwell are fun to watch.

But really, the entire film belongs to Sam Rockwell. Sam Rockwell can take the most predictable dialogue imaginable and make it sound like poetry. About halfway through the film, Bill loses his driver’s licence and is reduced to showing up at the games on bicycle. There’s little that is more adorable than Sam Rockwell pedaling across the screen.

The Winning Season is an incredibly sweet and likable movie. I’m glad that I discovered it.