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Artwork for Rolling with Difficulty

Rolling with Difficulty

Rolling with Difficulty Table
Planescape
Sigil
Dungeons & Dragons
Dungeons and Dragons
Beastlands
Mind Flayers
Character Development
Elder Brain
Grove Of the Unicorn
Per Aspera
Fortune's Wheel
The Beastlands
Chronosphere Of Lagos
Laurel Lockwood
Planar Trade Consortium
Nix
Open and Shut
Leveling Up
Mindflayers
Paladin

Throughout the Planescape there are countless wars between good and evil, lawful and chaotic. Forces of great power shift the very nature of reality. These are not their stories... Join Rolling with Difficulty as we explore the Planescape, following adventurers out on the Astral Sea, on the streets of the City of Doors, and beyond! Every episode of this D&D 5e actual play podcast follows a differe... more

PublishesWeeklyEpisodes134Founded4 years ago
Number of ListenersCategories
LeisureGamesFiction

Listen to this Podcast

Artwork for Rolling with Difficulty

Latest Episodes

This episode originally aired as a Patreon reward. For more talkbacks on systems we've tried, check out the Rolling with Difficulty Patreon page for those and much much more!

Noir, Red, and Austin get together to share their thoughts on Draw Steel a... more

Freshly in Brux, the Unicorn Knights are taking a brief break to get out of the rain. For the podcast the fun never stops though, as we answer your questions live!

---Our show contains fantasy violence (and the occasional foul language), treat us li... more

As old grudges come to a head, the Hunting Party takes their first real steps in Brux. Their path will lead them directly to the lair of Garou's greatest foe, but enemies of enemies have been known to become friends...

---Our show contains fantasy v... more

The way closed behind them the Hunting Party are finally in Brux! The welcome party is not unfriendly, but certainly not what our heroes expected...

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 prog... more

Key Facts

Accepts Sponsors
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Number of Listeners
Find out how many people listen to this podcast per episode and each month.

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Recent Guests

Linnie Schell
TTRPG player, DM, and creative director of Twice Roll Tales
Twice Roll Tales
Episode: Open and Shut Season 2 Episode 6: "Monstrous Intent"
Adam Gonzalez
Co-host from 5 GMs in a Podcast
5 GMs in a Podcast
Episode: Rolling with Difficulty Presents: "Heartwood Coven"

Hosts

Austin
Dungeon Master and central campaign organizer across multiple seasons; core host for Rolling with Difficulty campaigns.
Sophia
Host and editor/producer with co-hosting duties on Rolling with Difficulty campaigns.

Reviews

5.0 out of 5 stars from 1.7k ratings
  • I’m here against my will and I love it

    My brother sucked me in to this and now I can’t leave, but I don’t care

    Apple Podcasts
    5
    An ADHD teen
    Canada10 months ago
  • Best Actual Play Ever

    I love you guys so much you always find a way to make the most stressful decisions and events funny. Though I miss the Per Aspera campaign I have loved the Open and Shut campaign from what I’ve heard as well. Though I am also sad that the campaign has ended so short too I’m sure that the next campaign will be better than the last. The character interactions and Wally’s character in the Open and Shut campaign (though I can’t remember his name. XD) is great the accent is so good and I wanted to kn... more

    Apple Podcasts
    5
    MaplewoodReports
    United Statesa year ago
  • This podcast has my favorite piece of media I’ve consumed

    Vr-la’s monologue is worth it alone to consume every bit of this podcast to that point. It it my favorite piece of media I have ever consumed. And not just that speech but the entire podcast is beyond amazing. I envy people who get to listen to this the first time. The bit of Vr-la gives me goosebumps every time, even just thinking about it has that affect. Bravo noir, and thank you Sophie and red for osp that helped me end up here.

    Apple Podcasts
    5
    ChefJoe7
    United Statesa year ago
  • 👍🏻

    👍🏻

    Apple Podcasts
    5
    wowinthewold
    United Statesa year ago
  • I wait like a dog at the door for new releases

    Truly the most amazing DnD podcast I know of, worthy of rivaling CR itself. The stories are riveting, the characters are delightful, and the nonsense that makes Dungeons and Dragons so fun is potent and wonderful.

    Apple Podcasts
    5
    hello you are a nice person
    United States2 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Fans enjoy the balance between planning, combat, and humor, plus long-running storylines.
The show is highly praised for production quality and character interactions.
Listeners often highlight the DM's pacing and world-building strength.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Apple Podcasts
#103
United States/Leisure/Games
Apple Podcasts
#76
United Kingdom/Leisure/Games
Apple Podcasts
#134
Canada/Leisure/Games
Apple Podcasts
#175
Italy/Leisure/Games
Apple Podcasts
#229
Australia/Leisure/Games
Apple Podcasts
#22
Austria/Leisure/Games

Talking Points

Recent interactions between the hosts and their guests.

Hunting Party Q&A: Fresh Prey
Q: 1231720 question: How do you make D&D combat more strategic and give players meaningful choices?
They emphasize maps with varied terrain and environmental hazards, set clear objectives beyond simply killing enemies, and incorporate skill challenges and puzzle-like goals to force players to plan, coordinate, and use non-combat options to influence outcomes.
Hunting Party Q&A: Fresh Prey
Q: 563760 question: Was it always the plan to kill Vasilix this season, or did you envision a different role for him?
The plan evolved. The storyteller initially expected the big bad to be defeated earlier but adjusted as solo arcs lengthened the season. Keeping Vasilix alive for meaningful encounters allowed the party to meet and interact with him, increasing his weight and the drama of his eventual fate.
Hunting Party Q&A: Fresh Prey
Q: 126800 question: Where do you get your sources for building the Beastlands, and is it mostly canon, old books, or homebrew?
Austin explains that they pull ideas from canonical Planescape materials, especially second edition sources, and supplement with the Codex of the Infinite Planes and community wikis; they also rely on homebrew additions and live-session prep, often cross-referencing with the group's own live-streamed prep and Patreon posts.
Rolling with Difficulty Presents: "Writing Wrongs"
Q: What's the plan to stop Isaac?
The adventurers decided to use the collected counterphrases in a creative way to counteract Isaac's ritual, which involved themes of beauty, perception, and perspective.
Hunting Party Q&A: On the Scent
Q: What is your approach to designing combat for our high-level characters without leading to a TPK?
Austin explains that there is no specific formula; he relies on his experience and a bit of luck to balance the challenge level of combat encounters as the game progresses.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

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Frequently Asked Questions About Rolling with Difficulty

What is Rolling with Difficulty about and what kind of topics does it cover?

A high-production, long-form D&D actual-play set in the Planescape multiverse. Episodes center on intricate dungeon crawls, interplanar politics, and character-driven storytelling, with tactical combat, psionics, and heavy world-building. Produced with a coherent ensemble, the show blends humor, drama, and decision-driven outcomes across diverse campaigns, including Planescape adventures and one-shot sessions, often featuring elaborate combat sequences, clever homebrew rules, and a distinctive, ambient soundscape that supports an immersive fantasy experience. This mix of open-world exploration, planewalker intrigue, and strong DM stewardship tends to appeal to dedicated tabletop RPG players and fantasy fans who enjoy deep campaigns with ong... more

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Which podcasts are similar to Rolling with Difficulty?

These podcasts share a similar audience with Rolling with Difficulty:

1. Overly Sarcastic Podcast
2. Moviestruck
3. Push The Roll with Ross Bryant | Call of Cthulhu Improv TTRPG Podcast
4. Kill James Bond!
5. Worlds Beyond Number

How many episodes of Rolling with Difficulty are there?

Rolling with Difficulty launched 4 years ago and published 134 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Rolling with Difficulty?

Recent guests on Rolling with Difficulty include:

1. Linnie Schell
2. Adam Gonzalez

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