
Rolling with Difficulty
Hosted by Austin Funk and OSP Red and Sophia Ricciardi and Noir and Wally · Rolling with Difficulty Table
5.0from 1,636 ratings
- 146
- Episodes
- 82
- Transcribed
- 1,636
- Ratings
- Weekly
- Cadence
- 2021
- First episode
About 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!
- Publisher
- Rolling with Difficulty Table
- Category
- fiction · leisure
- Language
- en
- Explicit
- No
- First episode
- 3 Dec 2021
- Latest episode
- 6 Nov 2026
Latest episodes
82 of 146 episodes have a transcript.

6 Nov 2026TRANSCRIPT
Rolling with Difficulty Presents: "Journey of the Pennypack"

30 Sept 2026TRANSCRIPT
Hunting Party Q&A: Reel It In

18 Sept 2026TRANSCRIPT
Hunting Party Season 3 Episode 10: "The Eighth Eldest"
Who has been a guest on Rolling with Difficulty
Names identified in recent episode analyses. Showing up to five guests.
- Olivia
- JoCat
- Nando
- Imani
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
- Apple Podcasts (US)
- 4.9 / 5
- 224 ratings
- Spotify
- 5.0 / 5
- 1,412 ratings
Podcast Authority Score: 45 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
- Quality
- 32
- Social presence
- 94
- YouTube
- 0
- Engagement
- 99
Contact Rolling with Difficulty
- Guest appearances
- Does not typically book guests
Based on episode analysis; this does not confirm that the show is currently accepting guests.
Shows with a similar audience
Questions about Rolling with Difficulty
Who hosts Rolling with Difficulty?
Austin Funk and OSP Red and Sophia Ricciardi and Noir and Wally host the show. Published by Rolling with Difficulty Table.
How often do new episodes come out?
The show publishes weekly, based on its RSS feed.
Does Rolling with Difficulty take guests?
The show does not typically feature guests, based on episode analyses.
Where can I read transcripts?
82 of 146 episodes have a transcript on Pod Engine. Full transcripts are available with a Pod Engine plan.
Host of Rolling with Difficulty?
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