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Artwork for Rolling with Difficulty

Rolling with Difficulty

Rolling with Difficulty Table
Planescape
Dungeons & Dragons
Mind Flayers
Per Aspera
Mindflayers
Kyana
Vhas
Progenitor
Vlocketh
D&D
Psychic Damage
Baldur's Gate 3
Resurrection
Dungeons and Dragons
Cages Of Wasting
Spelljammers
Githyanki
Mechanus
Sigil
Virla

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

PublishesWeeklyEpisodes130Founded4 years ago
Number of ListenersCategories
FictionLeisureGames

Listen to this Podcast

Artwork for Rolling with Difficulty

Latest Episodes

Their greatest foe (so far) vanquished, the Unicorn Knights turn their attention to the portal scarring the Beastlands' first layer. With the aid of their portal expert, can they bring their knowledge to bare and close the entrance to Brux?

---Our s... more

It's been long enough. The will of the Great Wheel is coming for the Beholder Vasilix, and it arrives in the form of the vengeful Hunting Party...

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

In the aftermath of their battle with the Ape Lord the party has yet to heal. Tensions send heroes on their own paths with only the guidance of the other forces in the Beastlands, and each other, to guide them.

---Our show contains fantasy violence ... more

Dive into a thrilling story as Rolling with Difficulty plays Punderworld! When an evil Eye threatens the Punderworld, our four fearless readers must find the key phrases to stop him, using only their wits and wordplay!

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

Key Facts

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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People also subscribe to these shows.

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MoviestruckSophia Ricciardi
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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
    Canada9 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
#48
United States/Leisure/Games
Apple Podcasts
#80
Canada/Leisure/Games
Apple Podcasts
#159
United Kingdom/Leisure/Games
Apple Podcasts
#39
Italy/Leisure/Games
Apple Podcasts
#67
Australia/Leisure/Games
Apple Podcasts
#202
Italy/Leisure

Talking Points

Recent interactions between the hosts and their guests.

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.
Hunting Party Q&A: Picking Up the Trail
Q: Was there a particular plot or character moment that surprised you this season?
I had a good sense that Katya and Noir's character now revealed to be Kireek would probably be buddies, but I didn't realize it would be so immediately surprising.
Hunting Party Q&A: Picking Up the Trail
Q: How do you find an appropriate balance when playing with a more antagonistic group dynamic?
It's a matter of just the table you're at. I'm grateful to have a fantastic table that will allow me to play someone so irritating and antagonistic.
Hunting Party Q&A: Picking Up the Trail
Q: What was it like preparing a structure like this?
I think that perhaps there are less details than people would assume; actually, I think it was a lot easier to do it on the run than I originally planned.

Audience Metrics

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

Listeners per Episode
Gender Skew
Location
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?

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. Moviestruck
2. Overly Sarcastic Podcast
3. Worlds Beyond Number
4. The Magnus Archives
5. The Adventure Zone

How many episodes of Rolling with Difficulty are there?

Rolling with Difficulty launched 4 years ago and published 130 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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