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Rolling with Difficulty
Rolling with Difficulty
Author: Rolling with Difficulty Table
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© 2026 Rolling with Difficulty Table
Description
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!
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!
150 Episodes
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Go little to go big as Rolling with Difficulty tries out Humblewood! With special guests Olivia and JoCat, Red and Austin enter Sophia's tiniest adventure as they set off to find a new home for the Pennypack. Will they be successful? After all, the world is full of many dangers for creatures so small...---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-difficultyRolling with Difficulty Patreon:patreon.com/rollingwithdifficultyRolling with Difficulty Discord:https://discord.gg/8c9e4xhUKyMerch:https://crowdmade.com/collections/rolling-with-difficultyContact the Pod:[email protected] Feed: https://rollingwithdifficultypod.transistor.fm/Youtube: https://www.youtube.com/c/RollingwithDifficultyInstagram: @rollwithdifficultyBlueSky: @rollwithdifficulty.bsky.socialTik Tok: @rollwithdifficultyCast:Game Master - Sophia RicciardiBlueSky: @sophiekay.bsky.socialInstagram: @_sophie_kayMoviestruck: https://moviestruck.transistor.fm/Patreon: https://www.patreon.com/moviestruckSer Gareth - JoCatYouTube: https://www.youtube.com/c/JoCatTwitch: https://www.twitch.tv/jocatBluesky: @jocat.netTheodore - OliviaInstagram: @o.k.rosArt Instagram: @oliviarosartsRolls Untold: @rollsuntoldElwen the Shepherd - Austin FunkBlueSky: @atthefunk.bsky.socialThe Set's Journal of Faerun: https://www.dmsguild.com/product/345568/The-Sets-Journal-of-Faerun-Vol-1?term=the+setLakha - OSP RedBlueSky: @overlysarcastic.bsky.socialInstagram: @overly.sarcastic.productionsOverly Sarcastic Productions: https://www.youtube.com/c/OverlySarcasticProductionsChannel/Want to send us snail mail? Use this Address:Austin Funk1314 5th AvePO Box # 1163Bay Shore NY 11706Character Art by SophiaBackground Art by @tanukimi.sMusic by: Dominic Ricciardihttps://soundcloud.com/dominicricciardimusicFeatured Tracks:Hunt Downtime ThemeHunt Battle Theme
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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:https://crowdmade.com/collections/rolling-with-difficultyRolling with Difficulty Patreon:patreon.com/rollingwithdifficultyRolling with Difficulty Discord:https://discord.gg/8c9e4xhUKyMerch:https://crowdmade.com/collections/rolling-with-difficultyContact the Pod:[email protected] Feed: https://rollingwithdifficultypod.transistor.fm/Youtube: https://www.youtube.com/c/RollingwithDifficultyInstagram: @rollwithdifficultyBlueSky: @rollwithdifficulty.bsky.socialTik Tok: @rollwithdifficultyCast:Dungeon Master - Austin FunkBlueSky: @atthefunk.bsky.socialThe Set's Journal of Faerun: https://www.dmsguild.com/product/345568/The-Sets-Journal-of-Faerun-Vol-1?term=the+setKatya - Sophia RicciardiBlueSky: @sophiekay.bsky.socialInstagram: @_sophie_kayMoviestruck: https://moviestruck.transistor.fm/Patreon: https://www.patreon.com/moviestruckTrystine - OSP RedBlueSky: @overlysarcastic.bsky.socialInstagram: @overly.sarcastic.productionsOverly Sarcastic Productions: https://www.youtube.com/c/OverlySarcasticProductionsChannel/Kireek - NoirBlueSky: @noirgalaxies.bsky.socialInstagram: @noirgalaxiesGarou - WallyBlueSky: @wallydraws.bsky.socialInstagram: @stuckinspacePortfolio: https://ghost_astronaut.artstation.com/Want to send us snail mail? Use this Address:Austin Funk1314 5th AvePO Box # 1163Bay Shore NY 11706Character Art by @stuckinspaceBackground Art by @tanukimi.sMusic by: Dominic Ricciardihttps://soundcloud.com/dominicricciardimusic
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Content warning: thalassophobia, body modificationIn 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 occasional foul language), treat us like a PG-13 program!---Thank you to our friends over at Twice Rolled Tales! Check them out:https://www.twicerolled.com/Patreon: patreon.com/twicerolledtalesDani enamel pins available now! Order yours while supplies last:https://crowdmade.com/collections/rolling-with-difficultyRolling with Difficulty Patreon:patreon.com/rollingwithdifficultyRolling with Difficulty Discord:https://discord.gg/8c9e4xhUKyMerch:https://crowdmade.com/collections/rolling-with-difficultyContact the Pod:[email protected] Feed: https://rollingwithdifficultypod.transistor.fm/Youtube: https://www.youtube.com/c/RollingwithDifficultyInstagram: @rollwithdifficultyBlueSky: @rollwithdifficulty.bsky.socialTik Tok: @rollwithdifficultyCast:Dungeon Master - Austin FunkBlueSky: @atthefunk.bsky.socialThe Set's Journal of Faerun: https://www.dmsguild.com/product/345568/The-Sets-Journal-of-Faerun-Vol-1?term=the+setKatya - Sophia RicciardiBlueSky: @sophiekay.bsky.socialInstagram: @_sophie_kayMoviestruck: https://moviestruck.transistor.fm/Patreon: https://www.patreon.com/moviestruckTrystine - OSP RedBlueSky: @overlysarcastic.bsky.socialInstagram: @overly.sarcastic.productionsOverly Sarcastic Productions: https://www.youtube.com/c/OverlySarcasticProductionsChannel/Kireek - NoirBlueSky: @noirgalaxies.bsky.socialInstagram: @noirgalaxiesGarou - WallyBlueSky: @wallydraws.bsky.socialInstagram: @stuckinspacePortfolio: https://ghost_astronaut.artstation.com/Want to send us snail mail? Use this Address:Austin Funk1314 5th AvePO Box # 1163Bay Shore NY 11706Character Art by @stuckinspaceBackground Art by @tanukimi.sMusic by: Dominic Ricciardihttps://soundcloud.com/dominicricciardimusicFeatured Tracks:Hunting Party ThemeBig BattleWhen Will the Beast Land?The Beast Has LandedFinal Battle
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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 (and the occasional foul language), treat us like a PG-13 program!---Thank you to our friends over at We Are Legion! Check them out:We Are Legion: Libertines: https://linktr.ee/WeAreLegionPodDani enamel pins available now! Order yours while supplies last:https://crowdmade.com/collections/rolling-with-difficultyRolling with Difficulty Patreon:patreon.com/rollingwithdifficultyRolling with Difficulty Discord:https://discord.gg/8c9e4xhUKyMerch:https://crowdmade.com/collections/rolling-with-difficultyContact the Pod:[email protected] Feed: https://rollingwithdifficultypod.transistor.fm/Youtube: https://www.youtube.com/c/RollingwithDifficultyInstagram: @rollwithdifficultyBlueSky: @rollwithdifficulty.bsky.socialTik Tok: @rollwithdifficultyCast:Dungeon Master - Austin FunkBlueSky: @atthefunk.bsky.socialThe Set's Journal of Faerun: https://www.dmsguild.com/product/345568/The-Sets-Journal-of-Faerun-Vol-1?term=the+setKatya - Sophia RicciardiBlueSky: @sophiekay.bsky.socialInstagram: @_sophie_kayMoviestruck: https://moviestruck.transistor.fm/Patreon: https://www.patreon.com/moviestruckTrystine - OSP RedBlueSky: @overlysarcastic.bsky.socialInstagram: @overly.sarcastic.productionsOverly Sarcastic Productions: https://www.youtube.com/c/OverlySarcasticProductionsChannel/Kireek - NoirBlueSky: @noirgalaxies.bsky.socialInstagram: @noirgalaxiesGarou - WallyBlueSky: @wallydraws.bsky.socialInstagram: @stuckinspacePortfolio: https://ghost_astronaut.artstation.com/Want to send us snail mail? Use this Address:Austin Funk1314 5th AvePO Box # 1163Bay Shore NY 11706Character Art by @stuckinspaceBackground Art by @tanukimi.sMusic by: Dominic Ricciardihttps://soundcloud.com/dominicricciardimusicFeatured Tracks:Hunting Party ThemeWhen Will The Beast Land?Party Time TimeTense Moment
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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!---Dani enamel pins available now! Order yours while supplies last:https://crowdmade.com/collections/rolling-with-difficultyRolling with Difficulty Patreon:patreon.com/rollingwithdifficultyRolling with Difficulty Discord:https://discord.gg/8c9e4xhUKyMerch:https://crowdmade.com/collections/rolling-with-difficultyContact the Pod:[email protected] Feed: https://rollingwithdifficultypod.transistor.fm/Youtube: https://www.youtube.com/c/RollingwithDifficultyInstagram: @rollwithdifficultyBlueSky: @rollwithdifficulty.bsky.socialTik Tok: @rollwithdifficultyCast:Dungeon Master - Austin FunkBlueSky: @atthefunk.bsky.socialThe Set's Journal of Faerun: https://www.dmsguild.com/product/345568/The-Sets-Journal-of-Faerun-Vol-1?term=the+setKatya - Sophia RicciardiBlueSky: @sophiekay.bsky.socialInstagram: @_sophie_kayMoviestruck: https://moviestruck.transistor.fm/Patreon: https://www.patreon.com/moviestruckTrystine - OSP RedBlueSky: @overlysarcastic.bsky.socialInstagram: @overly.sarcastic.productionsOverly Sarcastic Productions: https://www.youtube.com/c/OverlySarcasticProductionsChannel/Kireek - NoirBlueSky: @noirgalaxies.bsky.socialInstagram: @noirgalaxiesGarou - WallyBlueSky: @wallydraws.bsky.socialInstagram: @stuckinspacePortfolio: https://ghost_astronaut.artstation.com/Want to send us snail mail? Use this Address:Austin Funk1314 5th AvePO Box # 1163Bay Shore NY 11706Character Art by @stuckinspaceBackground Art by @tanukimi.sMusic by: Dominic Ricciardihttps://soundcloud.com/dominicricciardimusicFeatured Tracks:Hunting Party Theme
★ Support this podcast on Patreon ★






