Ian Hobbs’s review published on Letterboxd:
I don't know what it is about gambling and casino movies but they always intrigue me and I always end up liking them more than I think, and with Joe Swanberg's Win It All that continues. I always see the Netflix movies on the suggested, but I never really watch them cause they always get a bad rep, so I don't know why I clicked this one, but I'm so glad that I did; because I had so much fun with it.
Co-written & directed by Joe Swanberg, Win It All is a sad and happy movie at the same time; having a man deal with his gambling problem in a new and unique way and I appreciate that a lot. The direction here is pretty strong as Swanberg handled intense, intimate, and funny moments with flare; there wasn't a dull moment in the whole 88 minutes of it's short runtime.
The performances here are the films greatest aspect. Jake Johnston absolutely, without a doubt, kills it as Eddie. He's so relatable, fun, and his characters arc never really goes through but it kinda does? It's hard to explain but it works. Joe Lo Truglio & Keegan-Michael Key were also fantastic additions to the cast.
It's a pretty underrated flick of 2017, and I definitely think everyone should check it out once. While the film is only 88 minutes the script doesn't have that many *high* points, it's just kinda mellow throughout and that's really the only downfall I found with it. Besides that, Joe Swamberg's Win It All is a nice, fresh, and entertaining film for any fan of gambling or poker.