The Pre-Timeline of Dimension 20
Just because I've seen a lot of confusion about this following the release of The Roll of a Lifetime: How Dimension 20 Sold Out Madison Square Garden, in which the story of how Dimension 20 got started is edited in such a way that viewers come away with an odd impression about the timeline, I thought I'd put together as clear and annotated a timeline as I can of how and when the Intrepid Heroes met, got into D&D, and got cast in Dimension 20, plus some of the greater context they were operating in. All of this is publicly available information, gleaned mostly from years of interviews, Adventuring Parties, NADDPod Short Rests, and social media posts.
1998: Noted science-fiction author Elaine Lee signs her ten-year-old son Brennan up for a Dungeons & Dragons game at October Country, a local comics and gaming shop, in order to provide him with a social and creative outlet after having to start homeschooling him due to pervasive bullying at school. Within weeks, he begins running his own games for fellow children.
December 1999: CollegeHumor.com launches, posting user-submitted funny and/or titillating content from around the web. Within a few years, banner ad revenue and merch sales have made its founders young tech millionaires. By 2004 they are hiring writers to produce original content.
August 2006: CollegeHumor is acquired by InterActive Corp. Shortly thereafter, Sam Reich is hired to produce video content on the strength of videos he'd posted online of his improv team Dutch West.
April 2007: CollegeHumor staff writers Jake Hurwitz and Amir Blumenfeld begin posting videos of themselves performing absurdist sketches in their downtime at work; this inspires the long-running Hardly Working series, in which CollegeHumor staff appear as heightened versions of themselves in the office.
2008: Brian Murphy is hired to answer phones at the CollegeHumor offices. He soon begins writing for the website and appearing in videos, striking up a nerdy friendship with staff artist Caldwell Tanner.
2011: Emily Axford is hired by CollegeHumor as part of a wave of new talent as the original CollegeHumor cast moves on to bigger opportunities. She and Murph are memorably cast as romantic interests in Jake & Amir videos; some time later, they begin dating.
Early 2014: CollegeHumor's video team relocates to Los Angeles in order to establish themselves as a traditional TV production house, including shows like Adam Ruins Everything and the Jake and Amir series Lonely and Horny. Murph and Emily are among the cast who make the move. They marry in September and begin developing the TV sketch show Hot Date.
Early 2015: Siobhan Thompson, Zac Oyama, and Grant O'Brien are hired to write and act in sketches for CollegeHumor as cast turnover continues. Emily and Siobhan become close friends, and Zac bonds with Murph and Emily over anime.
August 2015: Jake and Amir, having quit CollegeHumor earlier that year, start the podcast network Headgum, whose initial slate of podcasts is shows by other CollegeHumor alums.
November 2015: Brennan Lee Mulligan wins $50,000 on Who Wants to Be a Millionaire?, pays back a loan for medical expenses, and begins the process of relocating to Los Angeles to pursue more opportunities in production and development.
July 2016: Siobhan throws herself a birthday party, inviting people she knows from doing comedy in New York and Los Angeles. At the party, Emily overhears Brennan talking about D&D and corners him to ask him to run a game for her and her friends. During the conversation, Zac turns around, asking what they're talking about, and gets invited too. Siobhan, Zac, Emily, Murph, and Adam Ruins Everything producers Jon Wolf and Travis Helwig start playing in a home game with Brennan DMing. Murph plays a paladin, Emily a druid, Siobhan a ranger, and Zac a monk.
Around the same time: Lou Wilson meets Brennan through Upright Citizens Brigade (where Brennan coaches improv) and begins playing in a different home game as a barbarian. Both of these games are played in 3.5, Brennan's preferred edition of Dungeons & Dragons at the time.
September 2016: Murph, Emily and Caldwell start 8 Bit Book Club, a podcast about video game adaptations, on the Headgum network.
April 2017: Ally Beardsley is hired (along with Raphael Chestang and Rekha Shankar) to join the CollegeHumor sketch-video cast, as Siobhan has left to pursue other opportunities and Murph and Emily are busy with Adam Ruins Everything and Hot Date. During this round of hiring, Brennan is considered but doesn't make the cut, although a few months later he is hired part-time to write questions for Um, Actually. Ally and Zac become close friends and perform improv together.
Summer 2017: Zac leaves CollegeHumor to write on a new season of Adam Ruins Everything. Rather than go through another round of auditions and hires, Sam bumps Brennan up to main cast.
Fall 2017: Wanting more of a return out of their investment, IAC insists on CollegeHumor starting its own streaming service. Existing staff are required to pitch original shows. Brennan is halfway through writing a pitch document for a TTRPG actual play, citing the success of The Adventure Zone and Critical Role, when he is called into a meeting and asked how he would feel about DMing an actual play.
October 2017: Brian Murphy guests on If I Were You, Jake and Amir's flagship podcast, and explains Dungeons & Dragons. Jake is intrigued, Amir not so much.
November 2017: Dimension 20 begins the planning stages. For the next three months, Brennan works with producer David Kerns, coordinator Ebony Hardin, director Michael Schaubach and designer Rick Perry to develop a unique set, feel, and pace for the show. After some chemistry test games, the initial cast is set as Brian Murphy, Emily Axford, Siobhan Thompson, Zac Oyama, Lou Wilson, and Rekha Shankar, who has never played before.
December 2017: At a Headgum Christmas party, Jake Hurwitz corners Murph and suggests that they start a D&D podcast so that Jake can play.
January 18, 2018: Murph, Emily, Caldwell and Jake announce Not Another D&D Podcast on an episode of 8 Bit Book Club.
February 7, 2018: The first shooting day of Fantasy High, which will be the first season of Dimension 20. Only a few weeks before shooting, Rekha has a scheduling conflict and can't fit Dimension 20 in between her duties as head writer of CollegeHumor's sketches and developing other shows for Dropout; Ally Beardsley becomes her replacement at the Dimension 20 table. It is Ally's first time playing D&D at all; it is Brennan, Zac, Siobhan, and Lou's first time playing 5th edition. Earlier that day, Brennan shoots the first CEO video, which will net him viral notoriety and a vocal fanbase within the CollegeHumor audience, with an undercurrent of "finally, a straight white man" to the praise.
February 8, 2018: The first campaign episode of Not Another D&D Podcast is released. It releases weekly thereafter, and they are 32 episodes in and have done their first live show before Dimension 20 premieres.
September 26, 2018: The first two episodes of Fantasy High are available when Dropout goes live. It is the immediate breakout hit of the platform, so much so that the second season, The Unsleeping City, goes into production while Fantasy High is airing; but because it will take so long to edit before it's ready to air, a short "sidequest" is filmed in a weekend with Matt Mercer, Erika Ishii, Amy Vorphal and Ify Nwadiwe from the online gaming world and Mike Trapp and Rekha from CollegeHumor to tide the audience over, establishing D20's production rhythms for the next several years.
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