From awkward teens navigating high school to a ‘Game of Thrones’-inspired food fight
By Jacey Gibb, Distribution Manager
I have an unwavering bias towards Dimension 20, the tabletop roleplaying show from streaming platform Dropout. When the first season debuted in 2018, I’d played Dungeons & Dragons (D&D) a handful of times, but never really gelled with it. I’d even dabbled with some D&D podcasts to no avail. Then, along came the nearly two-hour pilot, appropriately titled “The Beginning Begins.”
D20 was cheeky. It never lost sight of what it was, and it featured seven of my favourite CollegeHumor (CH) cast members sitting around a table, just yukking it up together. The silliness and humour have 100 percent been influential in my own D&D journey. However, even a devote fan like myself can admit the seasons vary in quality.
Here is my breakdown, from bottom of the (still high) barrel to *chef kiss* magnificent:
5. Tiny Heist (Season Four): On paper, D20’s fourth season and second sidequest looks amazing. The McElroy family (of The Adventure Zone and My Brother, My Brother, and Me fame) join D&D newcomers/CH cast members Lily Du and Jess Ross for a pint-sized heist to steal a roll of quarters. Tiny Heist features a slew of memorable supporting characters, but the group dynamic just isn’t there. The McElroys’ wealth of D&D experience often overshadows the lesser-experienced players, and the plot feels very one-track. That said, the set pieces and character design for this season are incredible, and it’s almost worth it for Justin McElroy’s character alone, a knock-off LEGO man-slash-master of disguise.
4. The Unsleeping City (Season Three): Dungeon Master Brennan Lee Mulligan’s love for New York City is unwavering (he even wrote a sketch back in 2018 titled “Don’t Trash Talk New York,” where he hilariously rails against people dissing his hometown.) Unsleeping City is meant as an homage to the world-famous city but with a real-life magical twist: the aging Broadway star is in fact a faerie half-elf; the down-on-his-luck nurse from St. Owen’s Hospital is actually a cleric; the super-jacked firefighter is actually a paladin. The campaign is littered with shoutouts to NYC (digs at the inconsistent subway schedule, SantaCon being a secret purge of demonic Santa clones, and even Pizza Rat!) which even I could appreciate, as someone who’s never been there. The season is a ton of fun and features some incredible battles, but the exposition overload in the later episodes really muddle the stakes.
3. Escape from the Bloodkeep (Season Two): I fucking love D20’s first sidequest, so don’t let its placement at number three fool you (numbers one and two are just that good.) Mulligan assembles an all-star cast (including Matt Mercer) to form a team completely of villains. It feels jarring, hearing a typical fantasy narrative entirely from the villains’ perspective, but the characters are played with such humour and richness that you often forget they are the ones trying to stomp out the forces of good. My only complaint about EFTB is its short episode-run of only six episodes.
2. Fantasy High (Season One): The first season of D&D set the bar impossibly high, following six teen misfits learning the ins and outs of being a hero at their adventuring academy. The cast is bursting with iconic characters, but Beardsley’s corn-worshipping Kristen Applebees stands out immediately, along with Axford’s rebel tiefling Fig Faeth. Imagine the characters of Breakfast Club but they ultimately have to try and save the world—all while navigating crushes and trying to avoid detention. This season was popular enough to inspire Dimension 20: LIVE, which followed the same characters through their sophomore year.
1. A Crown of Candy (Season Five): What a satisfying juxtaposition, having the darkest and most ruthless season of D20 be the one where everyone plays animated food. Focusing on the royal family of House Rocks, ACOC interweaves political and religious intrigue like no other season. Did I mention how fucking brutal this season is? Multiple characters permanently die, real tears are shed by the cast (and myself), and the sets and minis look good enough to eat. The stakes have never felt more real, and the world-building never more absurd than in D20’s latest season.