Chris’s review published on Letterboxd:
Win it All is a low-key comedy about a gambling addict, who, of course, is a perpetual loser. He's then given the ultimate temptation for an addict, a bag full of money to look after for a period of time.
The film works largely because Jake Johnson can play a charming loser perfectly well. Amidst the humour, the film actually deals with addiction and the process of attempting to beat an addiction pretty well and the ironic subversion of the moral of the story is very nicely done.