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 different entry in our adventures, and are intended to be watched in any order your heart desires. Follow the tale from the beginning, or jump in along the way, however you listen it's sure to be a wild ride!
Chart trend
Position in the Games chart (US), last 90 days.
#1#55#108JunJulAugSep
#26
all-time peak
114
days in the top 50 since Nov 2024
Latest episodes
Showing 20 · updated from the feed
Hunting Party Season 3 Episode 8: "Black Swan"
#13 trending · Games
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
Sep 4 4 h 36 min
Hunting Party Season 3 Episode 7: "Storm's Edge"
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
Aug 28 4 h 26 min
Hunting Party Season 3 Episode 6: "Twisted Fates"
Content Warning: Character Conflict, Character Death
The fractured party splits only further. As each Knight loses themselves in their own obsessions, will they remember
Aug 21 4 h 09 min
Hunting Party Q&A: Gone Fishin'
The party is split but the cast is together! We answer your questions in our mid-season Q&A!
---Our show contains fantasy violence (and the occasional foul language), tr
Aug 12 57 min
Hunting Party Season 3 Episode 5: "Seer Astray"
Alone again, Katya is drawn by the threads of destiny towards the Prowl. Who, or what, awaits the Seer Stray there?
---Our show contains fantasy violence (and the occas
Aug 7 2 h 51 min
Hunting Party Season 3 Episode 4: "Foul Tides"
One wizard poorer, the remaining Unicorn Knights resolve to focus on their quest. The bivalves wait for no one, but they are not the only ones lurking in the Sessile Pool
Jul 31 4 h 22 min
Hunting Party Season 3 Episode 3: "Reflections: Part 2"
Garou is dead, but if the party has their way it won't be for long. His life is not simply in the hands of Kireek however, and as great forces tangle for his mortal soul
Jul 24 2 h 38 min
Hunting Party Season 3 Episode 2: "Reflections: Part 1"
Content Warning: Character Death
In search of a solution to the Aboleth's toxic waters, the Hunting Party makes for the refuge of the Gnamma. Across the desert's sands w
Jul 17 4 h 33 min
Hunting Party Season 3 Episode 1: "A Broken Song"
Awakening in the relative safety of the Blackstone Lodge, the Hunting Party reunites and begins their hunt for the aboleth cursing the waters of Brux. Their first lead ta
Jul 10 4 h 11 min
Rolling with Difficulty Presents: "The New Nexus Knights"
Welcome to the New Nexus Academy! In a world of Superheros and villains, only one school can teach young crime fighters to wield their powers with great responsibility, a
Jul 3 3 h 02 min
Rolling with Difficulty Presents: "Dark Heart of the Wood"
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 gue
May 8 4 h 42 min
Rolling with Difficulty Talkback: Draw Steel
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 m
Apr 24 1 h 08 min
Hunting Party Q&A: Fresh Prey
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!
---Ou
Apr 8 1 h 09 min
Hunting Party Season 2 Episode 10: "Rainfall"
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
Mar 27 4 h 35 min
Hunting Party Season 2 Episode 9: "Riddles and Rats"
The way closed behind them the Hunting Party are finally in Brux! The welcome party is not unfriendly, but certainly not what our heroes expected...
---Our show contains
Mar 20 2 h 36 min
Hunting Party Season 2 Episode 8: "Lists and Layers"
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,
Mar 13 3 h 38 min
Hunting Party Season 2 Episode 7: "Vasilix"
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 f
Mar 6 5 h 15 min
We're Level Fourteen!
When you slay a Beast Lord, your get to level up! I don't make the rules, I just write about them here in the episode descriptions - Sophia
---Our show contains fantasy
Mar 2 12 min
Hunting Party Season 2 Episode 6: "Fracture"
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 Be
Feb 27 3 h 12 min
Rolling with Difficulty Presents: "Writing Wrongs"
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
Feb 20 2 h 06 min
Chart positions
Where Rolling with Difficulty ranks today in each Apple Podcasts chart (US, Sep 7, 2026).
A curated, balanced selection of Apple Podcasts reviews.
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.
ChefJoe7 · Mar 2025
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.
hello you are a nice person · Sep 2024
I found this podcast via a couple of the players other works (shout out Sophia and Red of Moviestruck and OSP respectively) and I tried to get into it early on without much success. I bounced off of it like I have with most actual play podcasts at first while just trying to listen casually, but thanks to a long road trip recently I got through enough episodes to make it through the train heist and subsequent planescape high speed chase episodes and I've been hooked since! Austin is a masterful DM and really putting his all into this adventure, and I love his house rules for monks and crits especially. Everyone has fun characters and play's them well. Sophia does a great job editing and producing and the show is well paced, a solid adventure in each episode so far while maintaining a fun continuity. It definitely took everyone an episode or two to start feeling comfortable, but the time investment has been well worth it! Highly recommended even(or especially if) you've bounced off of other less edited real play podcasts, or if you're tired of the material plane in your campaigns and want a DnD adventure based on a more sci-fi-fantasy high concept. The show pitches a kind of Cowboy Bebop/Firefly vibe; but the crew quickly come together as more of a group of heroes exploring the planescape in a very Star Trek kinda way. Love the show, love the cast and crew and characters, loving the music(which they've added more of on the second season and I'm hoping that continues as I make my way thru!) Also special thanks again to OSP shouting out the podcast enough that I remembered it long enough(after four seasons XP) to give it a second try and get hooked properly this time!
Kiton · Aug 2023
I was brought here by Red and Indigo (Sophia/Danni) and stayed because I fell in love with these goofy little nerds. In every episode I legit laugh out loud (much to the confusion of my roommate and neighbors who have no idea what I’m listening to) and love the all the background mumblings and whispers throughout the adventure. I can’t wait until January for Season 3 so that I can have more adventures!
MrDCConn · Sep 2022
We strive to present a balanced view by showing a diverse range of reviews from Apple Podcasts.
Here you find the Apple Podcasts chart positions of Rolling with Difficulty, its latest episodes to listen to directly, and reviews from listeners. Rankings are updated daily for the United States.
