Rolling with Difficulty

Rolling with Difficulty

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!

Episodes

March 6, 2026 315 mins

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 program!---

Thank you to our friends over at Hilarity Save RPG! Check them out:
https://beacons.ai/hilaritysaverpg
BlueSky: @hilaritysaverpg.bsky.social
Instagram: @hilaritysa...

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

Dani enamel pins available now! Order yours while supplies last:
https://crowdmade.com/collections/rolling-with-difficulty

Rolling with Difficulty Patreon:
patreon.com...

Mark as Played
February 27, 2026 192 mins

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 (and the occasional foul language), treat us like a PG-13 program!---

Thank you to our friends at Burnt Cook Book Party! Check them out here:
www.BCBParty.com
Episode One "K...

Mark as Played

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

Thank you to our friends at Twice Rolled Tales! Check Punderworld out here:
Back Punderworld on Ki...

Mark as Played
February 18, 2026 66 mins

Aberrations continue to fall to our Unicorn Knights, but their hunt is not over yet! They are taking a brief intermission to answer some of your questions about their campaign though.

---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:
https://crowdmade.com/collections/rolling-with-difficu...

Mark as Played

The lair of the Ape Lord looms and the only way to the root of this problem is through. Hoards of primates stand in their way, but that has never stopped the Hunting Party from reaching their quarry before...

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

Thank you to our friends at Twice Rolled Tales! Check Punderworld out here:
Back Punderworld on Kickstarter:...

Preparations made, it's time for the Hunting Party to investigate the cause of all this conflict in the Beastlands. They are not the only party interested in the central point of interest however, and their scouting mission may attract more attention than they anticipated...

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

Thank you to our friends over at Mage Hand H...

Mark as Played

Fresh off their victory over the would-be Ant Lord, the Hunting Party ties up loose ends. Some traverse the land in pursuit of their own mysterious goals, others forge new bonds, but all find themselves drawn deeper into the fold of the Beastlands...

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

Thank you to our friends at QueeRPG! Check them out here:
https://...

Mark as Played

Content Warning: Entomophobia, Fungi and Rot

The Beholder out of sight, the Hunting Party turns their attention to the vestiges of his work across the Beastlands. First up, the new colony knocking on their door. Can they unite to stand against the hive mind? Or is this Queen's gambit enough to finish the Unicorn Knights?

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

Mark as Played
January 19, 2026 12 mins

Just in time for new trouble in the Beastlands, the Hunting Party levels up!

---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:
https://crowdmade.com/collections/rolling-with-difficulty

Rolling with Difficulty Patreon:
patreon.com/rollingwithdifficulty

Rolling with Difficulty...

Mark as Played

Only a day after their encounter with the Beholder at the center of the schemes in the Beastlands, the Hunting Party barely stop to breathe before returning to the cave lair. Will this showdown bring an end to the turbulence in the Happy Hunting Grounds? Or are surprises in store for the newest Unicorn Knights?

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

Thank y...

Mark as Played

Content Warning: Cartoon Violence

Enter the rad dimension! In this Slugblaster adventure our tubular team of teens find themselves a heck of a lot closer to their favorite games than expected. Can they combo their way back to the real world? And just how many nachos can one teen consume? Find out all this and more in Jungle Jammed!

---Our show contains fantasy violence (and the occasional foul language), treat us like a PG-1...

Mark as Played
September 24, 2025 60 mins

After a successful season of Beastland antics, the crew gets together to answer your hardest-hitting questions!

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

Rolling with Difficulty Patreon:
patreon.com/rollingwithdifficulty

Rolling with Difficulty Discord:
https://discord.gg/8c9e4xhUKy

Merch:
https://crowdmade.com/collections/rolling-with-difficulty

Contact...

Mark as Played
September 12, 2025 192 mins

Content Warning: Party Conflict, Body Modification

Secrets revealed, the Hunting Party resumes their chase of Trystine's cousin. But they are not the only seekers in the Beastlands, and it's time some eyes were opened...

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

Thank you to our friends at Twice Rolled Tales! Check them out here:
https://linktr.ee/twiceroll...

Content Warning: Entomophobia, Creature Body Modification

After a brief respite, the Hunting Party is forced face-to-face with the final note on their map. Beyond the trees stripped bare, a reunion awaits...

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

Thank you to our friends at Burnt Cook Book Party! Check them out here:
www.BCBParty.com
Episode One "Kill ...

Mark as Played

The hunt continues, and after a brief detour to drop of the Warden somewhere safe, the Party enters the Domain of the Boar Lord. Her domain encroaches, but just who is leading the charge?

---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:
https://crowdmade.com/collections/rolling-with-difficu...

Mark as Played

Content Warning: Cannibalism, Arachnophobia

Finally taking a moment's respite, the Hunting Party regroups at the Grove of the Unicorn before heading back out into the Beastlands. Their prey? A missing Warden, hopefully to be found in one piece...

---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:...

Mark as Played

Content Warning: Entomophobia, Austin is Gross, Decay, These bugs wanna put eggs in things

Newly assembled, the Hunting Party follows the stench on the wind in pursuit of their first prey. Can this rag-tag group find common ground? Or will the belly of the beast prove too much for the Beastland's newest heroes?

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

VR-LA an...

Mark as Played
August 6, 2025 61 mins

We're halfway through the first season of Hunting Party! The cast gets together and answers the hardest hitting questions about our new crew of hapless heroes.

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

Rolling with Difficulty Patreon:
patreon.com/rollingwithdifficulty

Rolling with Difficulty Discord:
https://discord.gg/8c9e4xhUKy

Merch:

...

Mark as Played
August 4, 2025 12 mins

The Hunting Party is assembled and ready to level up! Let's see what these creatures of habit pick in this quick bonus before the adventures resume.

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

Rolling with Difficulty Patreon:
patreon.com/rollingwithdifficulty

Rolling with Difficulty Discord:
https://discord.gg/8c9e4xhUKy

Merch:

https://cro...

Mark as Played

Popular Podcasts

    If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

    Dateline NBC

    Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

    Betrayal Season 5

    Saskia Inwood woke up one morning, knowing her life would never be the same. The night before, she learned the unimaginable – that the husband she knew in the light of day was a different person after dark. This season unpacks Saskia’s discovery of her husband’s secret life and her fight to bring him to justice. Along the way, we expose a crime that is just coming to light. This is also a story about the myth of the “perfect victim:” who gets believed, who gets doubted, and why. We follow Saskia as she works to reclaim her body, her voice, and her life. If you would like to reach out to the Betrayal Team, email us at betrayalpod@gmail.com. Follow us on Instagram @betrayalpod and @glasspodcasts. Please join our Substack for additional exclusive content, curated book recommendations, and community discussions. Sign up FREE by clicking this link Beyond Betrayal Substack. Join our community dedicated to truth, resilience, and healing. Your voice matters! Be a part of our Betrayal journey on Substack.

    The Clay Travis and Buck Sexton Show

    The Clay Travis and Buck Sexton Show. Clay Travis and Buck Sexton tackle the biggest stories in news, politics and current events with intelligence and humor. From the border crisis, to the madness of cancel culture and far-left missteps, Clay and Buck guide listeners through the latest headlines and hot topics with fun and entertaining conversations and opinions.

    The Joe Rogan Experience

    The official podcast of comedian Joe Rogan.

Advertise With Us
Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2026 iHeartMedia, Inc.