Eddie (Jake Johnson, looking good shouldering a heavier role than usual) is a charming loser who can’t hold a decent job, hasn’t been to a meeting in six months, and squanders his nights and his money playing cards in underground speakeasies in Chicago.
When a lowlife associate headed to prison asks him to hold onto a bag full of ill-gotten cash for six months, we can all guess where this is headed for Eddie: rock bottom.
Win It All is both a smooth-edged comedy and an addiction drama fluent in the language of recovery. While the combination of the two is not always intellectually satisfying – Eddie’s whole charm is his nihilism, and it’s hard to imagine his happy ending sticking – Swanberg knows how to work the emotional levers of his audience. This is just the movies, after all. Like a good dealer, Win It All doles out the feeling that a guy like Eddie is chasing more than anything else: a reason to believe it’s all gonna work out beautifully.
Win It All
Narrative Spotlight, World Premiere
This article appears in March 10 • 2017.
