Jake Johnson, who co-wrote the screenplay, stars alongside Aislinn Derbez, Joe Lo Truglio and Keegan-Michael Key.

Eddie agrees, but a few days later gives in to temptation and opens the bag, finding several odd objects and a large sum of cash.

Although advised by his addiction recovery sponsor Gene not to touch the money, Eddie eventually takes $500 from the bag and gambles it.

He wins money, returns the $500 to the bag, and invites his friends to celebrate at the local bar.

He begins a downward spiral of gambling that ends with him owing the bag over twenty-one thousand dollars.

Eddie begins attending addiction counseling regularly and approaches his brother Ron for a job.

In August 2015, it was announced Joe Swanberg would direct the film, from a screenplay written by him and Jake Johnson.

[1][2] It was later revealed Aislinn Derbez, Joe Lo Truglio and Keegan-Michael Key had been cast in the film, and secretly shot in Chicago.

The website's critics consensus reads: "Win It All finds writer-director Joe Swanberg working in a comparatively mainstream vein -- and striking another collaborative spark with leading man Jake Johnson.