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Artwork for Rolling with Difficulty

Rolling with Difficulty

Rolling with Difficulty Table
Planescape
Sigil
Dungeons & Dragons
Beastlands
Dungeons and Dragons
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
Open and Shut
Nix
Leveling Up
Paladin
Mindflayers

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

PublishesWeeklyEpisodes147Founded5 years ago
Number of ListenersCategories
GamesFictionLeisure

Listen to this Podcast

Artwork for Rolling with Difficulty

Latest Episodes

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?

---Our show contain... more

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

Key Facts

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

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Recent Guests

Jack Lepiars
Guest player known from radio, performs as Jacques ze Whipper
Guest performer
Episode: Rolling with Difficulty Presents: "Dark Heart of the Wood"
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"

Host

Austin
Dungeon Master and host guiding sessions; central figure in multiple campaigns.

Reviews

5.0 out of 5 stars from 1.7k ratings
  • Up there among the best DND podcasts

    Podcast Addict
    5
    Dragion
    22 days ago
  • D&D

    The best dnd podcast I have ever listened to!!!

    Thank you Red for introducing me to the podcast.

    Apple Podcasts
    5
    Nodnarb9455
    United States4 months ago
  • Good DnD. Great 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.

    Apple Podcasts
    5
    dnd play
    United States4 months ago
  • 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
    Canadaa year 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

Listeners Say

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

Guests and DMing style are frequently highlighted as compelling and energetic, driving long-term engagement.
Fans cite strong world-building and character interactions as a major draw, with playful humor throughout.
Listeners praise high production quality and engaging editing, making complex narratives easy to follow.
The show's openness about safety and debriefs is noted as a positive, responsible model for shared storytelling.
Audience appreciation for nuanced mechanics explanations and accessible rules discussions.

Chart Rankings

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

Apple Podcasts
#116
United States/Leisure/Games
Apple Podcasts
#159
United Kingdom/Leisure/Games
Apple Podcasts
#190
Canada/Leisure/Games
Apple Podcasts
#116
Italy/Leisure/Games
Apple Podcasts
#132
Australia/Leisure/Games
Apple Podcasts
#35
Russia/Leisure/Games

Talking Points

Recent interactions between the hosts and their guests.

Hunting Party Q&A: Gone Fishin'
Q: How do you balance high‑level threats like the Aboleth slime with player agency?
The DM emphasizes letting players improvise and show resilience, using escalating slime points as a mechanic to raise stakes while still rewarding creativity and teamwork.
Hunting Party Q&A: Gone Fishin'
Q: Was the subclass change planned from the start?
No; the idea for Guru's class change emerged as the story unfolded and became a deliberate narrative decision to deepen the character and the Beastlands arc.
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.

Audience Metrics

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

Listeners per Episode
Gender Skew
Location
Interests
Professions
Age Range
Household Income
Social Media Reach

Frequently Asked Questions About Rolling with Difficulty

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

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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How many listeners does Rolling with Difficulty get?

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What are the audience demographics for Rolling with Difficulty?

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How many subscribers and views does Rolling with Difficulty have?

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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. Mom Can't Cook! A DCOM Podcast
4. Worlds Beyond Number
5. Humans

How many episodes of Rolling with Difficulty are there?

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.

How do I contact Rolling with Difficulty?

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Where can I see ratings and reviews for Rolling with Difficulty?

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What guests have appeared on Rolling with Difficulty?

Recent guests on Rolling with Difficulty include:

1. Jack Lepiars
2. Linnie Schell
3. Adam Gonzalez

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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