Synopsis
Win It All (2017) is an American comedy you can watch online on iFILM, directed by Joe Swanberg. Jake Johnson plays Eddie Garrett — a gambling addict who is fully aware he shouldn't be trusted with other people's money and does nothing useful with that awareness.
A friend heading to prison asks Eddie to hold a bag. Eddie agrees. The bag contains cash. He opens it. The money goes to poker. Now Eddie has a few months to win it back before his friend gets out, which is a terrible plan, and Eddie knows it. Meanwhile he meets someone — Aislinn Derbez — and finds himself wanting, for once, to be a person worth staying around.
Keegan-Michael Key shows up as Eddie's AA sponsor and steals every scene he's in. The film is low-key Chicago mumblecore: no musical swells, no redemption-arc speeches, just a guy being bad at self-control in a very recognisable way. Johnson makes Eddie likeable enough that you root for him even when he absolutely shouldn't be rooted for. Stream Win It All online on iFILM.
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