How you can make meeting your significant other’s family even more awkward? What if you had to do it on her grandpa’s literal death bed? So, is the cringe-comedy set up for Tim Wilkime’s Milton, a film that balances a broad comedic premise with subtle comedic timing and delivery.

We’ve learned to expect great things from writer/director Tim Wilkime. Last year, we featured his charming dramedy, Staycation (one of my favorite shorts from 2018). And, while Milton is certainly a stranger film—one that isn’t as grounded or emotionally resonate—there’s no denying Wilkime’s facility as a comedic director. Working with a cast of talented and recognizable faces (check out Stepsister and Strange Company), he crafts a piece that is thoroughly entertaining throughout its duration, balancing punchlines with the darker undercurrent of death. The set-up is compelling and the comedy has just the right amount of awkwardness: it pulls you in just to make you squirm.

The concept of one’s “last breath” is often a romanticized thing—a moment of finality that marks the end of an existence. But, really, in the grand scheme of things, it’s just another second in a stream of infinity. Time just marches forward, indifferent. And, so, Wilkime skewers the importance bestowed upon one’s final moments, juxtaposing it with the banality of awkward family meetings.

Not surprisingly, the film was based on a Wilkime’s real life experience. As he relates to Short of the Week:

“This is a semi-autobiographical story about my experience watching my then girlfriend, now wife's, grandmother pass away in hospice. I had to break the news to the family because they were catching up with each other and were unaware. It was very surreal watching someone take their last breath. I had only met the grandmother a few times before that but I felt very connected to her after her passing. It was a very emotional experience for me but years later, there was a lot of I found humorous about it as well which led me to writing this short.”

A veteran from College Humor, Wilkime is an established television and commercial director, so it’s exciting to see how he’s branching out into the world of shorts to tell original narratives. Crafting a successful joke on film isn’t easy. Making that comedy work with an undercurrent of drama? That’s doubly hard. But, considering Wilkime has done it twice in the past year with Staycation and Milton, we think it’s safe to say that this kid is going places...