You’re staring at the Dropout app. Or maybe you're scrolling through the Dimension 20 YouTube channel, eyes glazing over at the sheer volume of thumbnails. Brennan Lee Mulligan is grinning at you from a dozen different posters, sometimes in a suit, sometimes in a wig, and honestly, it’s a lot. You want to start. You’ve seen the clips of Brennan describing a "provolone" accent or Lou Wilson losing his absolute mind over a nat 20, but the barrier to entry feels like a brick wall.
Where do you even begin?
Here is the thing about the Dimension 20 watch order: it isn't linear. This isn't the Marvel Cinematic Universe where you have to watch twenty movies to understand why a purple guy is mad about rocks. It’s an anthology. Think of it more like American Horror Story or Black Mirror, but with more dice rolling and significantly more improvised comedy about capitalism.
The "Release Date" Trap
Most people tell you to start at the beginning. Fantasy High Season 1 was the spark that lit the fire back in 2018. It’s great. It’s iconic. But is it the best place for you? Not necessarily.
If you watch in strict chronological order, you’re watching the production team learn how to make the show in real-time. The first season is gritty and a bit raw. By the time you hit A Starstruck Odyssey, the production value is astronomical, the LED "Dome" is doing things that shouldn't be possible, and the editing is razor-sharp. If you’re a stickler for seeing the evolution of a craft, go chronological. Start with Fantasy High, move to The Unsleeping City, then hit A Crown of Candy.
But honestly? Most fans don't do that. They jump in where the "vibe" fits.
The Core Pillars: The Intrepid Heroes
If you want the "main" experience, you're looking for the "Intrepid Heroes" seasons. This is the core cast: Brennan Lee Mulligan as the Dungeon Master, with Emily Axford, Brian Murphy, Zac Oyama, Siobhan Thompson, Lou Wilson, and Ally Beardsley. They have a chemistry that is, frankly, borderline telepathic at this point.
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The Fantasy High Universe
This is the flagship. It’s The Breakfast Club meets Dungeons & Dragons.
- Fantasy High: Freshman Year (The beginning)
- Fantasy High: Sophomore Year (A live-streamed, more experimental journey)
- Fantasy High: Junior Year (The most recent evolution)
You must watch these in order. Do not skip to Junior Year. You’ll miss the emotional weight of why a character named Fig Faeth is having a mid-life crisis at age sixteen.
The Gritty and The Weird
Then you have the standalone Intrepid Heroes campaigns. A Crown of Candy is often described as Game of Thrones meets Candyland. It is brutal. Characters die. People cry. It’s some of the best dramatic acting in actual-play history. On the flip side, A Starstruck Odyssey is a chaotic, psychedelic sci-fi romp based on a comic series by Brennan’s mother, Elaine Lee. It’s fast-paced and uses the Star Wars 5e system.
The Unsleeping City (Seasons 1 and 2) is a love letter to New York. It’s urban fantasy at its peak. If you’ve ever lived in a city and felt like the subway was actually a portal to another dimension, this is your season.
The "Side Quests" and Where They Fit
Dropout frequently brings in guest DMs and "Side Quest" casts. These are shorter, usually 4 to 10 episodes, and they are perfect for people with commitment issues.
- Misfits and Magic: DM’d by Aabria Iyengar. It’s a parody of a certain wizarding school franchise, but it uses the Kids on Brooms system. It’s short, hilarious, and features Lou Wilson playing an American muggle who is confused by everything. It’s arguably the best "palate cleanser" in the entire catalog.
- The Seven: A spin-off of Fantasy High. You should probably watch Freshman Year first, but this all-female (and non-binary) cast playing a group of high-level maidens is pure high-octane energy.
- Dungeons and Drag Queens: Exactly what it sounds like. Bob the Drag Queen, Monét X Change, Alaska Thunderfuck, and Jujubee. It’s the best entry point for someone who has never played D&D in their life.
The Confusion Around "The Ravening War"
This is where the Dimension 20 watch order gets tricky. The Ravening War is a prequel to A Crown of Candy. It’s DM’d by Matt Mercer (of Critical Role fame).
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Should you watch it first because it’s a prequel? No.
The dramatic irony of The Ravening War only works if you know what happens in A Crown of Candy. You need to see the "future" of the world to appreciate the tragic origins of the conflict. Watch A Crown of Candy first. Always.
Does Order Actually Matter?
Kinda. For the "sequel" seasons, obviously yes. You shouldn't watch The Unsleeping City Chapter 2 before Chapter 1. But you can absolutely watch Neverafter (the horror season) without having seen a single second of anything else.
The biggest mistake new viewers make is feeling like they have to "catch up." You don't. There are hundreds of hours of content here. If a season about tiny people living in a fridge (Tiny Heist) sounds boring to you, skip it. If a season about a regency-era social season (A Court of Fey & Flowers) sounds like your cup of tea, start there.
One thing to keep in mind: the mechanics change. Most seasons use D&D 5th Edition, but some use Kids on Bikes, Burning Wheel, or Good Society. If you’re a mechanics nerd, you might find yourself gravitating toward the 5e seasons first just for familiarity.
The Experimental Era
Lately, the show has been getting weird. Mentopolis takes place inside a guy's brain (think Inside Out but noir). Burrow’s End is about a family of stoats (think Watership Down but with more psychic powers). These seasons are incredible because they show the range of what actual-play can be. They don't require any prior knowledge of Dimension 20 lore.
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If you’re coming from Critical Role, you might find the pacing of D20 jarring at first. It’s edited. It’s punchy. Battles that take four hours in other shows are condensed into two-hour episodes with incredible miniature work by Rick Perry and his team.
A Practical Strategy for Beginners
If you want the most "balanced" experience, here is a suggested path:
- Fantasy High: Freshman Year (The classic start. If you aren't hooked by episode 2, maybe try a different genre.)
- Misfits and Magic (To see how different DMs and systems look.)
- A Crown of Candy (To see the show at its most high-stakes and emotional.)
- A Starstruck Odyssey (To see the cast at their peak comedic synergy.)
From there, you’re basically an expert. You can wander into the "Side Quests" or tackle the sprawling epic that is The Unsleeping City.
Don't let the "completionist" mindset ruin the fun. This isn't homework. It's a bunch of improv comedians sitting around a table telling stories that occasionally make you sob. The "correct" order is whatever keeps you hitting "Next Episode."
If you’re ready to dive in, the most actionable step is to pick a genre you already love—whether that’s high fantasy, sci-fi, horror, or regency romance—and find the corresponding D20 season. Check the Dropout schedule, because they are constantly rotating new concepts. Once you find the cast you love, the order will naturally fall into place based on what world you want to visit next.