Movie Review: Win It All

Win It All *** ½ / *****

Directed by: Joe Swanberg.

Written by: Jake Johnson and Joe Swanberg.

Starring: Jake Johnson (Eddie), Joe Lo Truglio (Ron), Keegan-Michael Key (Gene), Aislinn Derbez (Eva), Nicky Excitement (Nick), Arthur Agee (Arthur), Steve Berg (Berg), Cliff Chamberlain (Paul the Bartender), Kris Swanberg (Kris), Jude Swanberg (Jude).

 

Joe Swanberg is one of those filmmakers I respect, even if I’ve never really liked his films – of which, I’ve only seen a fraction of. He’s making the films he wants to make and doesn’t really care if you like them or not – so if I find his early work to be self-indulgent naval gazing, and his more recent work – where he’s trying something more mainstream – to not quite work, so be it. Few filmmakers seem willing to do what he does, and just keep churning them out. His most recent film – made for Netflix – is Win It All – and I think it succeeds where other recent stuff, like Drinking Buddies, failed for me. That film was an attempt at making a more mainstream romantic comedy – but with a twist, which is that the two people who are obviously perfect for each don’t get together. It was an interesting idea, but if you’re going to twist a cliché of the genre, you have to twist it into something – which is what he failed to do in Drinking Buddies (instead of it turning into a cliché, it turned into nothing).

 

Win It All takes another well-worn genre – the gambling addict movie – and attempts something similar. Fairly early in the film, Eddie (Jake Johnson) really, truly does realize he has a problem and goes straight. He starts working for his brother’s (Joe Lo Truglio) landscaping company – and surprises even himself with how much he enjoys it. He starts dating a nurse, Eva (Aislinn Derbez) who he genuinely likes, and wants to be with. He starts going to meetings, with the help of his sponsor Gene (Keegan-Michael Key). He has really, and truly turned his life around. There’s just one thing though – before he did all of that, he was given a bag by a scary looking friend, and told to hold it for him while he goes to jail for 6-9 months – and if he does, he’ll get $10,000. Of course, the bag contains money – under what looks like evidence of what could have been a fairly gruesome murder – and of course, Eddie gambles some of it away - $20,000 to be exact. He has a plan to get the money back – and it doesn’t even involve gambling. But then, he finds out his friend is getting out early – so, of course, he needs to head back to the tables, for one last time.

 

You could probably write many of the story beats of Win It All right now knowing nothing more about it. It’s not unlike The Gambler – either the James Caan or Mark Wahlberg version, or Rounders with Matt Damon, without an Edward Notion. Or countless other films. Yet, there is something genuinely different about Win It All as well – and it’s that middle section. The beginning, when Eddie falls down the rabbit hole into mounting debt, and the end – when he either has to win it all or get killed – we have seen but the middle, when he really does get clean is somewhat different. If there is a flaw in that, it’s the same type of flaw that was in Drinking Buddies – if you’re not going to follow the clichés, what are you going to follow? The middle section is fairly easy going, with great comic relief by Key and Truglio, and a sweet relationship between Eddie and Eva (including a rather chaste sex scene – by Swanberg standards). But all of that cannot fully cover up the fact that what we’re doing is watching someone do yardwork, and enter invoices into a computer for an hour. There isn’t much momentum there – and we know how the film will end.

 

But even during the rough patches in Win It All, there is Jake Johnson’s performance – which is the best I’ve seen from him in a film. His Eddie is kind of sweet guy – even if he is an idiot. He’s more believable as a broken down gambler than most of the stars who do it – in part because you really do believe that him being down $2,000 is horrible for him. The movie keeps things on a believable level throughout – and Johnson delivers a raggedly charming performance.

 

I didn’t much like the end of Win It All – it’s almost as if Swanberg and Johnson (who co-wrote the script together) didn’t really know how to get Eddie out of a certain situation, and just said screw it, and came up with something silly. But other than that, Win It All, is something more traditional from Swanberg – which isn’t really a bad thing. For one thing, for once, I enjoyed it.