In Greater Boston, a man wills himself to death because he can't handle the uncertainty of something as simple as a Roller Coaster due to his obsessive-compulsiveness. His roommate is given his eventual job at an astrology magazine thanks to his (possibly ghostly?) advice, and is given the job by a woman who hates her job and coworkers at said astrology magazine. His mystery-obsessed brother leaves a camp dedicated to seeing Bigfoot, only to quit and find work on a submarine trying to find the lost city of Atlantis. An eccentric college professor suggests that the Red Line of Boston secede from the city to become its own independent municipality.
Yes, it all sounds weird on the level of a certain other podcast, but it's all told with a completely straight face. The more surreal elements of the podcast, much like said other podcast, take a backseat to the complex relationships between the eccentric Bostonians to whom we are introduced. For example, while the story of Michael Tate - who is advised by what may be the ghost of his roommate Leon - could be construed as a ghost story, there's more emphasis on the fact that he's coping with his roommate's death and relapse into alcoholism, and attempting to get his life together. Though the circumstances through which he does so are somewhat more surreal than normal.
This is, this is, this is... Greater Boston's Tropes:
- The Alcoholic: Subverted by Michael Tate - while he makes admirable effort to be The Teetotaler, it's both implied and shown that when he falls off the wagon, (such as with the death of Leon) he falls hard.
- He reforms by the end of season one.
- Amusement Park of Doom: Wonderland's roller coaster is this for Leon. Subverted in that it wasn't the ride itself that killed him, but his own inability to deal with the anticipation.
- Claustrophobia: Inverted - Isabelle has a bad case of agoraphobia.
- Cloud Cuckoo Lander: Dmitri is seen as this by his siblings and most people that knew him, with his obsession with mysteries and bizarre problems - especially his anecdotes of living on a submarine - being seen as outlandish. Paul Chelmsworth, the "Mayor of the Red Line," an eccentric college professor, is a straighter example for his desire to create the Red Line as an independent city within Boston.
- Crossover: The podcast had one with the podcast The Amelia Project, where Chuck Octagon and the Greater Boston narrator meet main characters from The Amelia Project.
- Crystal Ball: Leon's ghost is trapped inside the one given to Gemma and it is used by Oliver to spy.
- Deadpan Snarker: Leon, especially when around Oliver.
- Ghostly Goals: Leon's seems to be to help Michael, but Oliver has other plans.
- Hostile Animatronics: Ethan has a few cheese robots from Wonderland, and they are pretty scary.
- Jerk with a Heart of Gold: Gemma. Seen as abrasive (Not unjustifiably so) by the rest of her workplace, but she was nice enough to give Michael a job. So there's that in her favor.
- Living Lie Detector: Melissa classifies herself as one.
- Love-Interest Traitor: Louisa's new boyfriend Phil is working with Oliver.
- The Maiden Name Debate: Male variant. Chuck considers taking Andy's name Wood, but Mallory convinces him to keep Octagon.
- Meaningful Rename: Gerald Poletti 'consults the ghost of Mary Wollestone Craft' to decides to change his name to Panda to Extinction Event to Dipsh*t. His co workers laugh at him behind his back, but he believes in the power of his name.
- Mundane Fantastic: Slightly surreal things happen daily - they just rarely directly impact the lives of the protagonists.
- Mysterious Backer: Few people know Oliver is the publisher of Third Sight and the backer of Emily's campaign.
- Phony Psychic: Subverted: though Gemma believes everyone at Third Sight is just BS-ing, it is shown some people at the company think it is real.
- Random Events Plot: ...Maybe?
- Real Joke Name: Yes, Chuck Octagon is not a fake name.
- Rich Bitch: Emily, though it turns out she isn't so rich.
- Schedule Fanatic: Leon Stamatas - to the point of planning out even the most mundane events months in advance on his calendar.
- Sir Swears-a-Lot & Cluster F-Bomb: Gemma often falls into this, but Mallory is the queen of the trope.
- Starts with a Suicide: A variant. Though whether it was a suicide is debatable (it's somewhat implied to be), Leon's death is in the first episode and sets off much of the events.
- Stock Unsolved Mysteries: Dmitri encounters a few on his journeys:
- He joins a group looking for Atlantis and finds it himself.
- He meets DB Cooper, who gives him some money and tells him a story.
- Underground City: The City of Red Line, as it was formerly (and still is) a subway. Not all of it is underground.
- Walk the Earth: Dmitri's current position.
- Wedding Smashers: Episode 22 is a disaster. Oliver and his group organize it so hot baked beans splatter down on the cast, scalding some people, and the broken train canopy destroys a couple of residences.
