
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 | 135 | Founded | 4 years ago |
|---|---|---|---|---|---|
| Number of Listeners | Categories | LeisureFictionGames | |||

Journey into Draw Steel and the Dark Heart of the Wood as Rolling with Difficulty attempts to heroically handle this official module in one shot fashion! With special guest Jacques ze Whipper, they journey into a haunted forest, in a desperate attemp... more
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
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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
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.
👍🏻
Key themes from listener reviews, highlighting what works and what could be improved about the show.
How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.
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Apple Podcasts | #158 |
Recent interactions between the hosts and their guests.
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This actual-play tabletop podcast mixes cinematic combat, intricate Planescape lore, and character-driven storytelling across evolving campaigns. Listeners often encounter cinematic dungeons, interplanar intrigue, and a stylish blend of humor and high-stakes decisions that reward longform worldbuilding and tactical play. A standout here is the balance between crunchy rules discussion and narrative moments, plus a rotating cast of players and a DM who emphasizes cinematic momentum, house rules, and early access to future arcs. Potential listeners who enjoy intelligent banter, large-scale adventures, and a strong sense of camaraderie will likely find it engaging and repeatable across seasons.
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1. Overly Sarcastic Podcast
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3. The Adventure Zone
4. Worlds Beyond Number
5. The Magnus Archives
Rolling with Difficulty launched 4 years ago and published 135 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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Recent guests on Rolling with Difficulty include:
1. Jack Lepiars
2. Linnie Schell
3. Adam Gonzalez
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