Win It All Review

Chicago-centric writer/director Joe Swanberg has teamed up yet again with Netflix and his favorite everyman actor, Jake Johnson, for another straight-shooting comedic drama in “Win It All.” Although Swanberg bets once more on his honest-to-goodness, real people living everyday life approach to storytelling, this film has a much stronger narrative focus, marking another step forward for the modern indie auteur.

In these last couple Netflix collaborations, starting with the limited anthology series “Easy,” Swanberg has improved upon his 2013 breakthrough “Drinking Buddies” by finding ways to up the stakes while staying true to the stories he wants to tell. Some audiences will crave more intriguing premises and manufactured melodrama and never quite get on board with him, but “Win It All” shows a willingness to compromise, if that’s a fair way to put it.

Johnson’s Eddie is in many respects an ordinary, struggling blue- collar Chicagoan without a job trying to find his way, but the dimension of his gambling addiction puts a fat caveat on his “everyday” dealings. When a buddy going off to prison hands him a duffel bag with the promise that if Eddie simply returns it untouched when he gets back, he’ll make $10,000, we’re already aware of his risk-inclined personality and know this will not go well. Whereas Hollywood would take this plot and turn it into a heist film or crime drama, Swanberg is just interested in Eddie’s roller coaster, and we’re instantly curious as to which end Eddie will come out when the credits roll.

It’s not quite accurate to call “Win It All” a portrait of gambling addiction; the film is all about Eddie, but there’s still a degree of distance between him and us – the objective is sympathy rather than empathy. Per Swanberg’s M.O., the real interest is in Eddie’s responses and choices, especially as it relates to the relationships in his life. His desire to change leads him to improve his relationship with his brother (Joe Lo Truglio), who wants nothing but to get Eddie on his feet, and lands him a new romantic opportunity in Eva (Aislinn Derbez from “Easy” episode “Controlada”).

Eddie’s ups and downs give a real pulse to this film that makes it a much more compelling watch than the casual attitude and mild conflict of “Drinking Buddies.” Swanberg captures his characters in such an earnest light, like no one else telling stories today, but that down-to-earth tone can result in dull plots. “Win It All” does a lot to mitigate that problem. The intensity still grades out at mild, but there’s a distinct hook.

Given the moral question hanging above the entire movie, Swanberg finds a really thoughtful and interesting way of ending the film that reminds us that Eddie’s journey is about a lot more than whether the film ends with him in the red or the black. It may come off a bit anti- climactic, but if you know Swanberg, you can’t watch this film expecting anything different. “Win It All” suggests there’s at least reason to keep betting on him going forward.

4/5 Stars

Win It All
Written and directed by Joe Swanberg
Starring: Jake Johnson, Joe Lo Truglio, Aislinn Derbez