| 101. | THE NINTENDO RANT - Best of Chuggaaconroy | 2:38 | |
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| 102. | Chuggaaconroy on His Future | 2:33 | |
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| 103. | TheRunawayGuys Leaderboards: Total Stars in Mario Party | 2:31 | | Mario Party
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| 104. | Chuggaaconroy's Favorite Video Game Music | 2:31 | | The Legend of Zelda: Majora's Mask
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| 105. | Chuggaaconroy Eats a Vegemite/Sardine Sandwich | 2:30 | |
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| 106. | Chuggaconroy Talks About Canceled Let's Plays | 2:30 | Let's Play |
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| 107. | It Doesn't Affect Misdreavus | 2:29 | |
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| 108. | Chuggaaconroy's Let's Plays Ranked by Views (June 2019) | 2:29 | Let's Play |
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| 109. | Chuggaaconroy - The Shelved LP That Lead to Chrono Trigger | 2:24 | Let's Play | Chrono Trigger
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| 110. | Chuggaconroy on Being a YouTuber in College | 2:23 | |
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| 111. | Chuggaaconroy's Thoughts on His Zelda LPs | 2:20 | Let's Play |
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| 112. | Nintendo Sent Chuggaaconroy a Nintendo Switch a Month Early! | 2:19 | | The Legend of Zelda: Breath of the Wild
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| 113. | Chuggaaconroy Talking About His Dad Compilation | 2:16 | |
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| 114. | Chuggaaconroy Loves Redheads | 2:16 | |
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| 115. | Chuggaaconroy's Thoughts on Yoshi | 2:16 | |
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| 116. | Chuggaaconroy's Let's Plays Ranked by Length (2008-2019) | 2:15 | Let's Play |
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| 117. | Introducing...TheRunawayGuys! | Anniversary Edition! | 2:10 | |
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| 118. | Chuggaaconroy the Hopeless Romantic (Compilation) | 2:09 | |
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| 119. | Chuggaaconroy on Recording DS Games | 2:07 | |
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| 120. | Chuggaaconroy Gets a Wedgie | 2:05 | |
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| 121. | Forest Maze - Chuggaaconroy | 2:04 | |
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| 122. | Chuggaaconroy Foreshadowing Let's Plays (Compilation) | 2:01 | Let's Play |
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| 123. | Chuggaaconroy on Majora's Mask | 1:59 | | The Legend of Zelda: Majora's Mask
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| 124. | "CAPITALISM" - Chuggaaconroy | 1:55 | |
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| 125. | Chuggaaconroy Hates the Postman | 1:55 | |
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| 126. | Chuggaaconroy Football Moments | 1:51 | |
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| 127. | Evolution of Chuggaaconroy's Editing | 1:50 | |
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| 128. | Waluigi in Super Mario 64 DS - Chuggaaconroy | 1:49 | | Super Mario 64 DS
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| 129. | "BIG" KEY - Chuggaaconroy (Mini-Compilation) | 1:48 | |
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| 130. | The Worst Feeling in the World - Chuggaaconroy | 1:47 | |
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| 131. | Chuggaaconroy on Current Let's Play Culture | 1:47 | Let's Play |
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| 132. | ONE TRY! | 1:46 | |
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| 133. | Chuggaaconroy - Power Outage | 1:46 | |
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| 134. | Mario & Luigi: Partners in Crime - Chuggaaconroy | 1:45 | |
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| 135. | Chuggaaconroy Made His Own DS Capture Card! | 1:45 | |
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| 136. | Chuggaaconroy on Disney/Pixar Sequels | 1:42 | |
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| 137. | Longest Tongue in the Galaxy - Chuggaaconroy | 1:41 | |
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| 138. | World Record - Chuggaaconroy (101 Power Bounce Combo) | 1:40 | |
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| 139. | Chuggaaconroy as TOADS | 1:40 | |
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| 140. | When Chuggaaconroy Used to Hide His Face | 1:35 | |
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| 141. | Why Chuggaaconroy is Afraid of Roller Coasters | 1:33 | |
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| 142. | Chuggaaconroy Does the Chubby Bunny Challenge | 1:33 | |
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| 143. | Chuggaaconroy on the Toy Story Series | 1:32 | |
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| 144. | I R SMRT - Chuggaaconroy | 1:32 | |
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| 145. | Chuggaaconroy Finds a Shiny Pokemon! | 1:31 | |
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| 146. | Chuggaaconroy Making Cybershell References | 1:31 | |
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| 147. | MURDERER! | 1:30 | |
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| 148. | Chuggaaconroy - Desert Levels | 1:29 | |
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| 149. | How Chugga Got His House | 1:29 | |
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| 150. | Chuggaaconroy on Moving to Twitch | 1:29 | |
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| 151. | PK STARSTORRRRRRMMMM! | 1:28 | |
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| 152. | Rest in Peace, Pippy. | 1:27 | |
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| 153. | Chuggaaconroy's Favorite Disney/Pixar Film | 1:26 | |
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| 154. | Chuggaaconroy's First Game Over in a Video | 1:26 | |
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| 155. | Saturday Night Fever - Chuggaaconroy | 1:25 | |
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| 156. | Why there are two A's in Chuggaa's Name | 1:25 | |
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| 157. | Chuggaaconroy on His Old Videos | 1:24 | |
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| 158. | 🎶 Chrono Trigger: The Musical! 🎶 - Chuggaaconroy | 1:24 | | Chrono Trigger
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| 159. | Chuggaaconroy's Sensor Bar | 1:23 | |
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| 160. | Chuggaaconroy Talks About His Depression | 1:21 | |
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| 161. | Chuggaaconroy's Designer | 1:19 | |
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| 162. | WHAT DO YOU MEAN I DID BADLY ON TIME (Chuggaaconroy Compilation) | 1:15 | |
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| 163. | "If They Ever Remade Link's Awakening..." - Chuggaaconroy | 1:13 | |
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| 164. | Chugga's Dream Comes True | 1:13 | | Mario Party DS
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| 165. | My Mom is HOT! | 1:12 | |
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| 166. | Steve the Trooper: Origins | 1:10 | |
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| 167. | I GRABBED ONTO THE LEDGE: The Lost Levels | 1:09 | |
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| 168. | TASTE THE RAINBOW MOTHERFU-- | 1:09 | |
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| 169. | Return of the Battery Meter | 1:09 | |
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| 170. | Timeline of Chuggaaconroy's Longest Let's Plays (2008-2019) | 1:07 | Let's Play |
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| 171. | Mikau's Song - Chuggaaconroy | 1:07 | |
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| 172. | TWO!?!? | 1:07 | |
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| 173. | "Chugga...are you dating Masae?" | 1:06 | |
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| 174. | Chuggaaconroy Nerds Out | 1:06 | |
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| 175. | Toolatetobehelpful | 1:05 | Let's Play |
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| 176. | Chugga Gets Jinxed. | 1:03 | |
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| 177. | Chuggaaconroy's Favorite Video Game Moments | 1:02 | |
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| 178. | Bee Movie but it's a Chuggaaconroy Reference | 1:02 | | Super Mario Galaxy 2
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| 179. | FOR THE LOVE OF... | 1:02 | |
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| 180. | SOMEBODY CALL CHRIS HANSEN | 1:02 | |
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| 181. | Chuggaaconroy ASMR: Pokemon Puns | 1:01 | |
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| 182. | PREVIOUSLY ON SUPER MARIO SUNSHINE... | 1:00 | | Super Mario Sunshine
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| 183. | "Their attacks are very weak." - Chuggaaconroy | 0:54 | |
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| 184. | Chocolate ( ͡° ͜ʖ ͡°) | 0:54 | | Super Mario Galaxy 2
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| 185. | Chuggaaconroy Explains Spaghettification | 0:53 | |
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| 186. | Chuggaaconroy on Stephen Hawking | 0:53 | |
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| 187. | The First Epic No - Chuggaaconroy | 0:51 | |
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| 188. | CHARLIE! - Chuggaaconroy | 0:51 | |
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| 189. | Illegal Chuggaaconroy Reuploads | 0:50 | |
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| 190. | Younggaaconroy | 0:49 | |
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| 191. | Daisy Strikes Back! - Chuggaaconroy | 0:46 | |
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| 192. | Should There Be More Toy Story Movies? - Chuggaaconroy | 0:45 | |
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| 193. | What Chugga's Family Thinks | 0:40 | |
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| 194. | Mike Wazowski'd | 0:39 | |
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| 195. | Chuggaaconroy Ruins Your Childhood! | 0:37 | |
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| 196. | Black Holes - Chuggaaconroy | 0:37 | |
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| 197. | Slip of the Tongue | 0:37 | |
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| 198. | Moscow - Chuggaaconroy | 0:36 | |
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| 199. | Origin of the Hiker Dance | 0:35 | |
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| 200. | WHY DID YOU DO THAT!? | 0:35 | |
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