Written and directed by former NFL wide receiver Matthew A. Cherry, Almost 30 is a coming-to-terms comedy about the life of 27 year old Justin (Michael Moss), and the disarray he’s thrown into when his marriage proposal leads to his breakup.

Working a bottom rung office job, newly single and soon to be homeless, Justin’s life could be going better. Almost 30 tackles that uncomfortable feeling that time has passed you by and you’re suddenly so old and yet achieved so little. Despite the seemingly gloomy premise Almost 30′s lighthearted and playful tone makes a directionless life at 27 not seem so bad, though the comic edge does rob the show of some emotional depth.

Shot with a fly on the wall documentary style that has its characters inexplicably sharing thoughts with the camera, Almost 30 is peppered with surreal touches, such as a horseback ride straight from the cover of a Mills & Boon novel, or a search for a roommate that quickly becomes an episode of The Voice. These unexplained, often throwaway moments are what really give the series it’s contemporary, carefree vibe. The world that Justin is navigating isn’t “anything goes” crazy, but writer/director Cherry never passes up an opportunity to make a good joke.

Starting with some uncharacteristically raw performances and camerawork, episode 1 may not instantly capture you, but is absolutely worth sticking with. Clocking in a just over six minutes long, the firt episode of Almost 30 quickly finds its footing when it introduces one of the funniest new characters in a sitcom, Justin’s best friend Ricky (Ricky Smith).

Absolutely stealing the show in episode 2, Ricky is the perfect counterpoint to Justin’s likeable yet downtrodden victim of circumstance. Opinionated, opportunistic and often thoughtless, Ricky’s brash and self serving disposition conspire to give him all of the show’s best lines – lines he knocks out of the park with his frank “tell it like it is” delivery.

Unlike the typical “character we love to hate” that Ricky may sound like on paper, the truth is Ricky is never anything less than likeable. He’s flawed but charming, and in a believable way.

In fact, Cherry clearly has a knack for unique or otherwise standout characters, as Sherial McKinney similarly shines in her supporting role as Dream – Justin and Ricky’s supervisor who confounds genre stereotyping by being interesting, multifaceted and impossible to cleanly label.

With great humour, rich characters and a documentary style that supports the comedy instead of smothers it, it should be little surprise that Almost 30 was able to snag itself a finalist position in Comedy Central’s Short Pilot Competition. Currently optioned by Comedy Central with the chance of becoming a televised series, there’s no word yet on precisely where future episodes of this promising series are going to air – whether on YouTube or our dusty set-top boxes.

Whilst it would undoubtedly be a shame for the internet to lose such a quality series as this, I’m sure the phrase about loving something and letting it go applies here, or something… I don’t know. I’ve never owned birds.

In a rare moment of lucidity from the YouTube community, I feel commenter IIslha puts it best…