Starring: Jake Johnson, Aislinn Derbez, Joe Lo Truglio
Director: Joe Swanberg
Running Time: 90 mins
Win It All is an American film about a gambling addict who finds himself in hot water after he gambles away $50,000 he had been entrusted with guarding by a man soon to be released from prison.
Win It All is a film with some great charisma, brought to life by a fantastic central performance by Jake Johnson. However, what really makes the film is its riveting and sobering portrayal of addiction, powerfully capturing the endless rabbit hole that can – at worst – entirely ruin a person’s life.
That makes things sound a little dark, however, and the strength of Win It All is its ability to blend that very challenging and uncomfortable central theme with what is an undeniably rather fun and entertaining story.
Counting on good humour and a fast pace throughout, the story of Johnson desperately trying to recuperate the funds he lost before he gets whacked is actually a fairly entertaining part of the movie. It’s not necessarily there to get laughs, but Win It All isn’t afraid to look back in on itself and poke fun even at the darkest moments.
And there are indeed some very dark moments here, as Johnson finds his entire world falling apart when he realises what’s happened to the money he’s meant to be protecting. However, while that puts him right at rock bottom, that means there is only way forward: up.
That’s perhaps the crux of what makes this movie such a charming and ultimately uplifting watch. While there is dark and challenging drama throughout, it’s interspersed with wonderfully heartwarming drama, as we see Johnson finally begin to appreciate his life by getting a job and entering into a relationship.
In tandem with the film’s excellent humour, that’s the kind of story that really gives hope to you even in the darkest moments, suggesting that there’s always a way forward away from rock bottom.
Overall, I really enjoyed Win It All. A thoroughly captivating watch from start to finish, the film features brilliantly engrossing and often challenging drama that combines with an uplifting and heartwarming story, good humour and a great central performance to deliver a great watch throughout. So, that’s why I’m giving the film a 7.5.