Offices & Bosses is a spin-off miniseries of the main podcast. The tabletop role-playing game Offices & Bosses was introduced in episode 32, "Offices & Bosses", when Arnie, Chunt and Usidore met Metamore. In this series Metamore returns to reprise his role as Office Manager and guide the other players through their campaigns.
All three seasons were originally available on Earwolf. Season 1 of O&B was released to the main feed between Seasons 2 and 3, and Seasons 2 and 3 of O&B are now available to Patreon members, with an additional introduction from the High Time Queen to provide context and spoiler warnings.
| Offices & Bosses | |
| Offices & Bosses logo | |
| Hosts | Arnie, Chunt, Usidore the Blue |
| Release | |
| First episode | January 11, 2017 |
| Network | Patreon (originally on Stitcher) |
| Production | |
| Producers | Arnie Niekamp (Seasons 1–2) Evan Jacover (Seasons 1–2) Ryan DiGiorgi (Seasons 1–2) Adal Rifai (Season 3–) |
| Theme music | Andy Poland |
| Logo | Allard Laban |
Cast
Season One
In Season One, Arnie, Chunt and Usidore are joined by Metamore as Office Manager and several of their friends as they attempt to collect the Q4 numbers.
| Character | Class / Position | Player |
| N/A | Office Manager | Metamore |
| John Bastion | Marketing Manager | Usidore |
| Dan Smith | Temporary | Chunt |
| Orlando Bloom | Elf | Arnie |
| Gail Davidson-Durst | I.T. Professional | Flower |
| Gail Davidson-Durst | I.T. Professional | Krom the Barbarian |
| Gail Davidson-Durst | I.T. Professional | Singing Sword |
| Gail Davidson-Durst | I.T. Professional | Caball'on Valentin |
Season Two
Metamore returns as Office Manager for another campaign. This time they’ll be playing the new “Unemployed” expansion.
| Character | Class / Position | Player |
| N/A | Office Manager | Metamore |
| John Bastion | Previously Employed | Usidore |
| Danger La Grange | Trust Fund Baby | Chunt |
| Hayden Christensen | Art School Graduate | Arnie |
| Mr. Ropely | Landlord | Dorian Deville |
| Ron Bingo | Junkie | Klax |
| Marilyn Beef | Lunch Lady | Claudia |
| Matthew Bernstein | Aspiring Model | Chest Trünkborn |
| Mariska Hargitay | Orphan Pickpocketer | Momo |
| Mark McGrath | Street Kid | Chip von Pierre |
| Angelique | Street Kid | Bippy von Pierre |
| Dr. Daniel Pyledriver | Level 3 Garageband Member | Dripfang |
Season Three
Traach the Kobold takes over as Office Manager for an exciting new campaign featuring the Chief Executive version of Offices & Bosses.
| Character | Class / Position | Player |
| N/A | Office Manager | Traach |
| Clairm Collaite-Mug | Usidore | |
| P.J. Success | Seasonal Manager | Chunt |
| The Masked CEO | Vampire | Arnie |
| Tony Obsidian | Hornelius the Fintaur | |
| Blame Racoon | Culture Captain | Jayme Ragoon |
| Shame Racoon | Culture Captain | Sayme Ragoon |
| Charles Smartcock | Tomblain Belaroth | |
| Larry Lumpkin | Metamore | |
| Sonia Harding | Trainwreck | Flower |
Season Four
Chunt takes over as game master for an exciting new campaign featuring the Teachers & Classrooms expansion pack.
| Character | Class / Position | Player |
| N/A | Game Master | Chunt |
| Lloyd Master-Chief | High School Student | Usidore |
| Stoney Rivers | High School Student | Momo |
| Lhu | High School Student - also a Cthulhu | Arnie |
| Clarice Templeton | High School Student | Hildy Shiblin |
Season Five
Metamore returns as Office Manager for a new campaign set at a large multinational tech company in Silicon Valley.
| Character | Class / Position | Player |
| N/A | Office Manager | Metamore |
| Warmie Hammer | Sales | Arnie |
| Ron Zertnert aka The Nerts | Marketing Manager | Chunt |
| Jenny “Gonzo Nom-Nom” Ergonomics | Secretarial Pool | Usidore |
| Kelly “Kellmobile” Giorn-Lohman | Intern | Hildy Shiblin |
| Dr. Daniel Pyledriver | Head of Building Management and Operations | Dripfang LeDesparé |
| William H. (The “H” stands for the “The Cooler”) Macy | Water Deliveryperson | Fluff the Squirrel |
Episodes
Season One
Season One began airing in January 2017, on the Earwolf premium service Howl (later merged into Stitcher Premium). It was released for free on the main feed starting April 2019, during the hiatus between Seasons 2 & 3. It is set at the time of episode 92, "Resonance Stone". Arnie, Chunt and Usidore are joined by Flower, Krom The Barbarian, Singing Sword and Caball'on Valentin in a quest to attain the Q4 numbers.
| No. in season | Title | Original air date |
| 1 | "Flower From I.T." | January 11, 2017 |
| The game of Offices & Bosses begins! Metamore plays Office Manager guiding Arnie, Usidore, Chunt and Flower on an adventure to attain the Q4 numbers. | ||
| 2 | "Krom from I.T." | January 18, 2017 |
| Krom the Fingarian joins the campaign to retrieve the Q4 numbers, as our band of adventurers contends with…Happy Hour! | ||
| 3 | "Singing Sword From I.T." | January 25, 2017 |
| The Singing Sword joins our heroes for a battle in a Panera. There is stabbing. | ||
| 4 | "Caball'on from I.Tree" | February 1, 2017 |
| A talking tree joins the campaign as our team enters the deadly Company Retreat. | ||
| 5 | "The I.T. Team" | February 8, 2017 |
| Everything comes to a head at the office Holiday Party. | ||
| 6 | "Teachers & Classrooms (Live from Very Very Fun Day in Chicago)" | April 12, 2017 |
| Metamore has an expansion pack for the game. And Flower is back to play. | ||
Season Two
Season Two began airing in April 2018 via Stitcher Premium, set around the time of Season 2, episode 53 "Advanced Offices & Bosses".
A live episode was recorded at the Bootleg Theater, Los Angeles, on April 22, 2018.
These episodes were made available to Patreon members on February 17, 2022.
| No. in season | Title | Original air date |
| 1 | "Skeleton Roommate" | April 4, 2018 |
| Klax the Skeleton joins Arnie, Usidore and Chunt for an all-new game of Offices and Bosses, led by Metamore. | ||
| 2 | "Witch Roommate" | April 11, 2018 |
| Claudia the witch joins the game, as the players visit a job fair. | ||
| 3 | "Mimic Roommate" | April 18, 2018 |
| Chest Trünkborn the Mimic joins the game as the players take on a catering gig. | ||
| 4 | "Mouse Roommate" | April 24, 2018 |
| Momo the mouse with human strength joins the game as the players accept a mysterious delivery job. | ||
| 5 | "Vampire Neighbors" | May 1, 2018 |
| The vampires Chip and Bippy stop by to play squatters living next door. Sure hope you like Star Wars! | ||
| BONUS | "Blue Tiger Team-up (Live from LA)" | May 8, 2018 |
| The magical Blue Tigers play a special offshoot game Office Managed by Chunt. Recorded live on April 22, 2018 at the Bootleg Theater in Los Angeles, CA. | ||
| 6 | "Necromancer Bandmate" | May 15, 2018 |
| Dripfang joins the game as the campaign turns towards starting a band. | ||
| 7 | "The TV" | May 22, 2018 |
| The Funemployed campaign comes to a close and Klax returns to play Ron Bingo. | ||
Season Three
Season Three began airing in January 2020 via Stitcher Premium, set sometime during Season Three of the main podcast.
These episodes were made available to Patreon members on March 3, 2022.
| No. in season | Title | Original air date |
| 1 | "Chief Executive Fintaur" | January 30, 2020 |
| Hornelius the Fintaur helps kick off a new season of Offices & Bosses with new Office Manager, Traach the Kobold! Arnie, Chunt and Usidore introduce their latest characters for this exciting Chief Executive version of O&B! Who will be the first to reach C level?! Is Arnie a vampire?! Grab your stapler and die and let's get rolling! | ||
| 2 | "Chief Executive Bathroom Boys" | February 6, 2020 |
| Arnie, Chunt and Usidore make their way into the higher ups bathroom and try to work their corporate magic! | ||
| 3 | "Chief Executive Holiday Twins" | February 13, 2020 |
| While admiring an erotic sculpture garden the hosts stumble upon old….friends(?) Jayme and Sayme. Arnie, Chunt, Usidore and the twins then 'roll up' to the corporate holiday party and let's just say things go south from there. | ||
| 4 | "A Series of Chief Executives" | February 20, 2020 |
| Uh oh! Reserve the conference room because Tomblain Belaroth joins the gang for an intense meeting! Be prepared…you're going to want to eat some pizza while enjoying this episode! | ||
| 5 | "Chief Executive Metamore" | February 26, 2020 |
| The boys stumble upon their old friend and Office Manager, Metamore! They can’t resist one round of O&B with him for old times sake! | ||
| 6 | "Chief Executive Flower Finale!" | March 4, 2020 |
| In the O&B season 3 finale the crew runs into Flower who adds a dash of chaos to the search for the final Sigma! Fingers crossed for only rolling 7's! | ||
Season Four
Season Four began airing in January 2024 exclusively on Patreon, set after Season Four of the main podcast.
These episodes were posted to Patreon beginning on January 11, 2024.
| No. in season | Title | Original air date |
| 1 | "The First Day of High School" | January 11, 2024 |
| Chunt is the Game Master for Offices and Bosses: Roll Call. Three freshmen played by Arnie, Usidore, and Momo work together to rule the school! | ||
| 2 | "Freshmen" | January 25, 2024 |
| As freshmen year continues, Arnie, Momo, and Usidore fight for their very lives and try to avoid improv class. | ||
| 3 | "Senior Year" | February 8, 2024 |
| It's time to put on the senior play (and for everyone to fall in love with Clarice). | ||
| 4 | "Prom" | March 7, 2024 |
| Tonight is the most important boss battle of their lives. | ||
| 5 | "Reunion" | March 21, 2024 |
| 20 years later, the gang must defeat at curse at their class reunion. | ||
Season Five
Season Five began airing in June 2026 exclusively on Patreon, set after Season Five of the main podcast.
These episodes were posted to Patreon beginning on June 11, 2026.
| No. in season | Title | Original air date |
| 1 | "New Edition" | June 11, 2026 |
| Metamore is back! Let's roll up new characters and start working at InSysTek! | ||
| 2 | "Orientation" | June 18, 2026 |
| Hildy joins the party as they meet Thad, the Orientation Tech Bro. | ||
| 3 | "Office Birthdays" | July 16, 2026 |
| Dripfang joins the gang to help plan the monthly birthday for the office. | ||
| 4 | "The Top Floor" | July 30, 2026 |
| Fluff the Squirrel joins the team as they ascend the building's elevator to C-Suite. Also, be sure to place your order for Cheesy Edible Triangles™ HERE! | ||