“Julio was literally down by the schoolyard.”

Having built a reputation as one of the preeminent mumblecore directors, Joe Swanberg’s improv style of the directing has gathered a bit of cult status. That status particularly grew after Drinking Buddies, an entirely improvised film, premiered at the 2013 SXSW Conference. Fans of this style may be disappointed to hear Win It All was scripted (with Jake Johnson co-penning the screenplay).

Yet if you weren’t aware of this style change you might not even notice. The conversations built on the imagination and wit of Swanberg’s actors in the past are now mostly up to Swanberg and Johnson’s vision on paper, creating something clearer with an enhanced naturalism that improv provided for Swanberg’s first projects.

At last year’s SXSW, Swanberg gave a keynote address that dared filmmakers to take risks. Just as writing a script seems to be a risk for him, that’s also reflected in the plot of Win It All, following a gambling addict, Eddie (Jake Johnson) who comes into a pile of money during a losing streak. He’s asked to hold onto a gym bag for a friend heading to prison for six to nine months, and is told not to look inside until he’s out. In return, he’ll get $10 thousand. Instead of putting the bag away, he opens it up and slowly chips away, betting the bag contents away and in turn his life, since his friend gets an early release.

Eddie tries to hold it all together by betting even more but keeps digging his hole deeper, eventually enlisting the help of his gambling addiction counselor, (Keegan-Michael Key), and his brother (Joe Lo Truglio). But the biggest gamble taken by Eddie is trying to swing a new relationship with a girl (Aislinn Derbez) he meets at a bar during one of his winning streaks.

It all boils down to Swanberg’s continuous dissection of modern relationships. In Drinking Buddies and Digging for Fire (also co-written by Johnson), it was platonic relationships between guys and girls that were probed. Here, there’s a greater focus on developing a love interest while also digging at the bond between brothers and friends that will do anything for the blackest of sheep in the family. If we’re getting really technical, the relationship with money is also at the center of this all, but the human bonds both created and resurrected are at the heart.

There is one inherent issue with the entire premise. If Eddie is betting away his life, he’s either going to win it back or lose it all. If he wins it all, there’s not much of a lesson learned and only feeds the idea that one lucky move can change a person’s life. If he loses out, it’s a bleak life that awaits Eddie (his parallels to Fast Eddie from The Hustler are too great to be a coincidence.)

But that can be forgiven, as the process to get to the end makes for thoroughly smart comedy. While Johnson and Lo Truglio have shown their chops on our TV screens on New Girl and Brooklyn Nine-Nine and do a more than fine job here as well, the MVP is Keegan-Michael Key. As the taller half of Key & Peele and a MADtv alum, he’s used to scripted work but has an ability to make it all seem like improv and command each scene — all exclusively shared with Johnson.

Also at the aid of Swanberg is his song selections. While never known as a music-heavy director or one to conduct show-stopping scores, his tracks have typically had a good effect on the story. His selection of old soul and R&B songs, while old school and unexpected, completely sell Eddie’s troubled soul with ease.

While Win It All is not a complete break from Swanberg as far as overall structure and subject matter (another Chicago-based film) are concerned, the sum is greater than the sum of its parts and should have fans excited for more of his official scripts in the future.

8/10