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Artwork for Rolling with Difficulty

Rolling with Difficulty

Rolling with Difficulty Table
Planescape
Sigil
Beastlands
Dungeons & Dragons
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
Nix
Open and Shut
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

PublishesWeeklyEpisodes149Founded5 years ago
Number of ListenersCategories
GamesFictionLeisure

Listen to this Podcast

Artwork for Rolling with Difficulty

Latest Episodes

Reunited and off to Karasuthra, but first, a Q&A!

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

VR-LA and Vhas enamel pins available now! Order yours while supplies last:

crowdma... more

Content warning: thalassophobia, body modification

In the darkest depths, in the Library of all Knowledge, the Aboleth awaits. Can our Hunting Party prevail? Or will they be swallowed by the deep?

---Our show contains fantasy violence (and the occ... more

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

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
    2 months 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 States5 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
#106
United States/Leisure/Games
Apple Podcasts
#81
Canada/Leisure/Games
Apple Podcasts
#181
United Kingdom/Leisure/Games
Apple Podcasts
#81
Australia/Leisure/Games
Apple Podcasts
#95
Italy/Leisure/Games
Apple Podcasts
#39
Ireland/Leisure/Games

Talking Points

Recent interactions between the hosts and their guests.

Hunting Party Q&A: Reel It In
Q: How do you find and sustain distinct character voices over extended sessions?
They suggest letting voice development come from the character, not forcing accents, practicing in advance, and using simple vocal shifts (register changes, timbre) to distinguish characters while keeping it sustainable.
Hunting Party Q&A: Reel It In
Q: How did you approach keeping players engaged and balancing different expectations at the table?
The panel recommends tailoring the game to what the players find interesting, adapting the planned plot, and using in-play adjustments or new challenges to keep everyone invested. They emphasize trust in the DM and openness to change when needed.
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.

Audience Metrics

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

Listeners per Episode
Gender Skew
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Interests
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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?

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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How many subscribers and views does Rolling with Difficulty have?

To see how many followers or subscribers Rolling with Difficulty has on Spotify and other platforms such as Castbox and Podcast Addict, simply upgrade your account. You'll also find viewership figures for their YouTube channel if they have one.

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. Worlds Beyond Number
4. The Magnus Archives
5. High Rollers DnD

How many episodes of Rolling with Difficulty are there?

Rolling with Difficulty launched 5 years ago and published 149 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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