Squaresville is a 32-episode web series that was created, written and directed by Matt Enlow and aired on Youtube from March 2012 until September 2013. It stars Mary Kate Wiles as the bored & restless, Zelda, and Kylie Sparks as the incredulous, sardonic, Esther, two best friends navigating their teenage years in suburbia and co-stars Austin Rogers as their neurotic, nerdy friend, Percy, Tiffany Ariany as former popular girl, Shelly, who Zelda befriends after her fall from grace and David Ryan Speer as Wayne, a delinquent who ends up dating Zelda and causing much of the drama in the series. Not surprisingly, Squaresville is often compared to Ghost World and Freaks & Geeks and, for the most part, it compares very favorably to both of them. While the situations in the series are often exaggerated for comedic purposes, they still remain very relatable and, even though the characters are based on classic archetypes, they're still unique and memorable.
Because Squaresville was created for the internet, its episode lengths range from just under two minutes to just over eight minutes and many episodes consist of only a single scene. This allowed Enlow to tell only as much of the story as needed to be told, without any extra filler and it also allowed him to try a number of experimental episodes. In the first season, there's one centered around two of Shelly's former, popular friends, that has only brief cameos from a few of the main cast members and another that's entirely devoted to examining one character's crutch phrase. In the second season, this experimentation is expanded with a series of monologues from all of the aforementioned actors as well as William Horwich, who has a recurring roles early in the season as, Jeremy, an acquaintance of Percy's and Christine Weatherup, who has a recurring role in both seasons as Zelda's sister, Sarah. There's also an episode that breaks completely from the narrative of the series and consists solely of Wiles, Sparks & Rogers cosplaying and referencing various movies & tv series. Admittedly, after most of the main story arc is resolved in episode 20, Squaresville does meander for a few episodes that are a bit hit or miss, but the series finds its footing again by episode 25 and ends just as strongly as it began. Monologues and experimental episodes aside, Squaresville doesn't really do much to innovate the classic teen drama/comedy, but it does a beautiful job of distilling the genre down to its most important elements and in that way not only measures up to it's better-known predecessors, but it might even exceed them.
I'll leave you with my favorite standalone episodes from each season and my favorite monologue. You can find the rest of Squaresville on Youtube and here's a playlist of just the episodes and monologues.
If there's a movie, recording artist, anime, podcast or any other media that you'd like me to check out for possible inclusion on the rec list, please contact me and let me know about it.