
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
| Publishes | Weekly | Episodes | 147 | Founded | 5 years ago |
|---|---|---|---|---|---|
| Number of Listeners | Categories | GamesFictionLeisure | |||

The final clams left to place, the Hunting Party enjoys a suspiciously calm series of deposits. This false security cannot last, and as the day ends, the reef looms. It's time to descend beneath the waves...
---Our show contains fantasy violence (an... more
Better belated than never! The party will need every advantage they can get to slay the Aboleth, so Austin graciously lent us a level-up.
---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-13 program!---
Da... more
The clam jam continues as the Hunting Party moves on to more sources of water in Brux. Next up, the Wells and the Synod. Old grudges rear their heads in the latter, will the Swanmays prove friends or foes for our Unicorn Knights?
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Clams in hand, the Hunting Party sets off to cleanse the waters and cut off their foe's means of escape. Brux is vast, but our heroes move quickly, and perhaps secure aid from some familiar faces along the way...
---Our show contains fantasy violenc... more
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Up there among the best DND podcasts
The best dnd podcast I have ever listened to!!!
Thank you Red for introducing me to the podcast.
This show is my favorite DnD podcast because it does a great job of being narratively entertaining while maintaining the joy of playing a casual game with friends. The characters are interesting, the way the players engage with game mechanics is fascinating, and the world of the planescape is excellently fleshed out. Plus, the music achieves tones and moods exactly as intended.
My brother sucked me in to this and now I can’t leave, but I don’t care
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
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Apple Podcasts | #116 | |
Apple Podcasts | #132 | |
Apple Podcasts | #35 |
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Rolling with Difficulty is a D&D 5e actual-play that takes listeners on planewalking adventures through Planescape-inspired settings, with a mix of strategic combat, intricate world-building, and character-driven storytelling. Episodes frequently center on party dynamics, backstories, and long-running arcs, while also exploring safety practices, debrief rituals, and the craft of crafting a compelling campaign. Noteworthy traits include a strong editing/production quality, rule explanations during play, and a willingness to experiment with multi-campaign formats—from high-fantasy Beastlands sagas to modern superhero one-shots—creating a versatile listening experience for tabletop enthusiasts and potential sponsors alike.
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These podcasts share a similar audience with Rolling with Difficulty:
1. Overly Sarcastic Podcast
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4. Worlds Beyond Number
5. Humans
Rolling with Difficulty launched 5 years ago and published 147 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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Rephonic pulls ratings and reviews for Rolling with Difficulty from multiple sources, including Spotify, Apple Podcasts, Castbox, and Podcast Addict.
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Recent guests on Rolling with Difficulty include:
1. Jack Lepiars
2. Linnie Schell
3. Adam Gonzalez
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