Eddie’s friend asks him to babysit a duffel bag for him, while he’s in prison. He’s not to touch it, not to open it. Just house it for the duration of the prison sentence, and he’ll be handsomely rewarded. But Eddie’s an addict. He’s not good at resisting temptation. He certainly doesn’t resisit this one, at least not for long. And when he finds loads of cash inside it, it triggers his gambling addiction, never exactly dormant, always waiting for a cash infusion.
Cut to – you guessed it – Eddie’s lost everything. He’s deeply in debt. He is drowning in regret. And also debt, duh. Eddie (Jake Johnson) takes his sob story to his older brother Ron (Joe Lo Truglio) who’s heard it all before but takes pity on him, and offers him a job in the family business. If Eddie works as a landscaper for the months remaining on the prison sentence, Ron will make up the difference in whatever else he owes. It’s a great deal, and Eddie throws himself into the honest work for the first time in his life, extra determined to turn things around because of a new woman on the horizon. But guess what? Prison buddy is getting out early! So the months-long plan to make the money back is now completely fucked, and so is Eddie. What shall he do?
Director Joe Swanberg is known for his low-budget, genre-blending stuff. He had such a good time doing Drinking Buddies that he decided to keep the mojo going with its star, Jake Johnson, and the two became a writing team who eventually came up with the script for Win It All. Jake Johnson is extremely charismatic, which helps sustain his losery character through lots of personal ups and downs. Pairing him with Joe Lo Truglio is the real stroke of genius. He’s affable and earnest, the exact opposite of the sleaze that pops up in Eddie’s other life. Keegan-Michael Key also pops up as his sponsor, who is sometimes shockingly and hilariously very un-sponsor-like.
The script is true to addictions without getting lost in their seriousness. It does go to some dark places, inevitably, but you can feel Johnson and Swanberg always tugging the reins back toward the light. It’s the little field trips from expectation that elevate this material about the normal schtick. Win It All ends up being a little slice of human nature with room for some character work. Falling into this film is a heady experience; it keeps subverting its own subversion, which keeps you on your twinkle toes. And possibly casting some side-eye to whatever duffel bags are in your closet.
Catch this film April 7 on Netflix.