| 101. | Episode 153 – Two Ettins Enter, 1 Ettin Leaves | 1:18:16 | |
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| 102. | Episode 106 – Kill Count Confirmed | 1:17:52 | Show |
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| 103. | Episode 160 – Matt Mercer Neck Tattoo And The People Who Love Them | 1:17:31 | |
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| 104. | Episode 78 – Et Tu, Panda? | 1:16:57 | Show |
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| 105. | Episode 178 – Gary Con Dungeons and Dragons 50th Anniversary | 1:16:22 | |
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| 106. | Episode 52- Welcome to the Pixie Brigade | 1:16:07 | Show |
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| 107. | Episode 101 – Grovel For Glory | 1:15:33 | Show |
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| 108. | Episode 157 – Planescape: Redux | 1:15:13 | Show |
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| 109. | Episode 75 – Jubilicious | 1:15:00 | Show |
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| 110. | Episode 146 – AI’s Back on the Menu Boys! | 1:14:57 | Show |
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| 111. | Episode 72 – A Little Bit of Chaos in Your Character is Good | 1:14:33 | Show |
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| 112. | Episode 149 – Lady Luck Has Dirty Dice | 1:14:17 | |
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| 113. | Grumpy Guest – Bruce 2: The Brucening | 1:14:15 | |
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| 114. | Episode 168 – Beware of Toilet Mimics | 1:14:08 | |
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| 115. | Episode 172 – The Champ Returns | 1:13:31 | |
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| 116. | Episode 116 – Do or Do Not | 1:12:53 | Show |
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| 117. | Episode 152 – I Want Candy! | 1:12:51 | |
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| 118. | Grumpy Guest – David Schirduan | 1:12:50 | |
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| 119. | Episode 145 – Roll on the Table | 1:12:37 | |
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| 120. | Episode 158 – Book of Many Grumpies | 1:12:05 | |
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| 121. | Episode 125 – Roll On Shock Table | 1:11:39 | Show |
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| 122. | Episode 79 – GDM Christopher Strikes Again | 1:11:26 | Show |
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| 123. | Episode 119 – I Aint Got Time To Bleed | 1:11:15 | Show |
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| 124. | Episode 18 – The Underdark Can’t Swim | 1:11:14 | Show |
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| 125. | The Underdark Can’t Swim | Grumpy Dungeon Master Podcast #18 | Dungeons & Dragons | 1:11:14 | Show |
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| 126. | Episode 94 – Monkeying Around | 1:11:09 | Show |
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| 127. | Episode 121 – OGL My! | 1:11:03 | Show |
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| 128. | Episode 173 – The Unchecked Power Of Chicken Hypnotism | 1:11:02 | |
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| 129. | Grumpy Guest – Kat Kruger | 1:10:49 | |
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| 130. | Episode 63 – Punisher the Puffinator | 1:10:49 | Show |
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| 131. | Episode 183 – An Expert Opinion | 1:10:43 | |
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| 132. | Episode 177 – Matt Mercers Name In Every Single Episode | 1:10:38 | |
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| 133. | Episode 187 – 16 Rules For Dungeons & Dragons | 1:10:35 | Show |
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| 134. | Episode 162 – D&D 50th Anniversary Leaks | 1:10:29 | |
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| 135. | Episode 84 – Elephants Can Fly! | 1:10:20 | Show |
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| 136. | Episode 132 – Uncle Ed Said | 1:10:13 | Show |
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| 137. | Episode 132 – Uncle Ed Said | 1:10:13 | Show |
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| 138. | Episode 67 – Somebody Play us Attune | 1:10:00 | Show |
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| 139. | Episode 170 – Worst Games Of All Time? Yes Please! | 1:09:38 | Show |
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| 140. | Episode 59 – Witchlight: The Reckoning | 1:09:10 | Show |
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| 141. | Episode 83 – Dice For All And All For Dice! | 1:09:04 | Show |
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| 142. | Episode 87 – Tagging With Dragons! | 1:09:00 | Show |
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| 143. | Episode 151 – So God And Godzilla Walk Into A Bar | 1:08:56 | Show |
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| 144. | Episode 176 – Gravity Always Wins | 1:08:55 | |
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| 145. | Episode 167 – Dungeon 23 and Me and Dracula | 1:08:52 | |
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| 146. | Episode 61 – Jay Doesn’t Read Good | 1:08:31 | Show |
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| 147. | Grumpy Guest – Reverendpanda | 1:08:21 | |
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| 148. | Episode 74 – Watering Whoville | 1:08:07 | Show |
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| 149. | Grumpy Guest Gronk the Gore-May | 1:07:49 | |
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| 150. | Episode 169 – Gee Wiz Kids & Grizzled Grannies! | 1:07:43 | Show |
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| 151. | Episode 182 – Return To Keep On The Borderlands | 1:07:37 | | Borderlands
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| 152. | Episode 188 – D&D 5. | 1:07:34 | |
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| 153. | Episode 161 – Which Came First? The Lizardfolk or the Aarakocra? | 1:07:31 | |
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| 154. | Episode 118 – Is Pathfinder Not Good Enough For You? | 1:07:24 | Show |
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| 155. | Episode 100 – Card Sharks | 1:07:15 | Show |
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| 156. | Episode 189 – A Valiant Effort | 1:07:14 | Show |
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| 157. | Episode 144 – Sigil, Outlands, and All the In-between | 1:06:44 | |
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| 158. | Episode 124 – Back To Business As Usual | 1:06:40 | Show |
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| 159. | Episode 91 – The Legend of Brapp Zanigan | 1:06:34 | Show |
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| 160. | Episode 128 – How Much Is Your Soul Worth? | 1:06:34 | Discussion |
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| 161. | Episode 37 – Seasons Don’t Fear the Gatekeeper | 1:06:28 | Show |
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| 162. | Episode 97 – Cr’aig Made an Appearance | 1:06:15 | Show |
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| 163. | Episode 154 – Be Careful Taking Gifts From Strange Game Masters | 1:06:14 | |
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| 164. | Episode 185 – Beyond D&D Homebrew | 1:06:14 | |
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| 165. | Episode 60 – Don’t Spider Open Inside | 1:06:01 | Show |
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| 166. | Episode 115 – DM’s Find A Way | 1:05:59 | Show |
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| 167. | Episode 76 – Negatives Good Buddy | 1:05:57 | Discussion |
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| 168. | Episode 130 – One Part Hurricane, Two Parts Firestorm, and Mix! | 1:05:56 | Show |
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| 169. | Grumpy Special Speculation | 1:05:54 | Discussion |
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| 170. | Episode 54 – Resurrection and You: A DMs Guide | 1:05:53 | Show |
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| 171. | Episode 36 – Electrum Economics-and You | 1:05:50 | Show |
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| 172. | Episode 73 – Grumpy Cookies and Korreds | 1:05:45 | Discussion |
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| 173. | Episode 49 – Fizbang’s Glorious Nerd Adventure! | 1:05:17 | Show |
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| 174. | Episode 103 – Where’s Chris? | 1:05:16 | Show |
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| 175. | Episode 136 – Warlock Snorlock! | 1:05:05 | Show |
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| 176. | Episode 85 – GDM Christopher Strikes Again Part III | 1:05:02 | Show |
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| 177. | Episode 174 – Death By Disintegration | 1:05:01 | |
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| 178. | Episode 50 – Gnoll Mercy!! | 1:04:45 | Show |
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| 179. | Episode 175 – Dungeon Crawl Killings | 1:04:44 | |
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| 180. | Episode 40 – Out of Time and Other Things Wizards Do | 1:04:18 | Show |
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| 181. | Episode 57 – Dungeons and Manga | 1:04:17 | Show |
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| 182. | The end of the year Grumpy Dungeon Masters Special, the Grumpy Dungeon Masters present: Grumpy Playe | 1:04:12 | |
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| 183. | Episode 68 – Ghost of Christmas Grumpy | 1:03:59 | Show |
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| 184. | Episode 159 – A Feast of Heroes | 1:03:57 | Show |
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| 185. | Tashas Hideous Whispers of Dissonant Laughter | Grumpy Dungeon Master Podcast #20 | D&D | 1:03:55 | Show |
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| 186. | Episode 20 – Tashas Hideous Whispers of Dissonant Laughter | 1:03:54 | Show |
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| 187. | Episode 66 – Duel of the Magic Items | 1:03:46 | Show |
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| 188. | Episode 120 – Riddle Me This | 1:03:33 | Show |
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| 189. | Episode 28 – 7 Habits of Highly Effective Crit Tables | 1:03:29 | Show |
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| 190. | Episode 99 – D&D Movie The Movie | 1:03:28 | Show |
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| 191. | Episode 111 – What’s Got Wing’s and Rolls? | 1:03:20 | Show |
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| 192. | Episode 179 – Christopher McNotopics | 1:03:20 | |
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| 193. | Episode 90 – Resurrection’s Stupid | 1:03:19 | Show |
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| 194. | Episode 140 – Revenge of the RPG Day | 1:03:13 | |
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| 195. | Episode 150 – Thaladred’s Tacos And Dice | 1:03:11 | |
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| 196. | Episode 58 – Sticks and Stones but Rules Changes Will Never Hurt Me | 1:03:06 | Show |
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| 197. | Episode 89 – Cover Me Cr’aig! | 1:03:05 | Show |
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| 198. | Episode 98 – Spelljammin Til The Break of Dawn | 1:03:04 | Show |
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| 199. | Episode 56 – The Chris Episode Spectacular | 1:03:01 | Show |
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| 200. | Episode 45 – GDM Chris Leaves the House | 1:02:53 | Show |
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