| 301. | Travel Via Plant is a dumb D&D spell | High Rollers: Aerois #shorts | 60 | | High Rollers
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| 302. | High Rollers: Aerois #183 | The Infinite Staircase | 60 | | High Rollers
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| 303. | Into Dangerous Lands | Altheya: The Dragon Empire #37 | 59 | |
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| 304. | High Rollers: Aerois #167 | Open the Cargo Door | 58 | | High Rollers
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| 305. | High Rollers: Aerois #151 | The Stalking Sickness | 58 | | High Rollers
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| 306. | High Rollers: Oneshot - ROOT THE RPG #AD | 58 | | High Rollers
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| 307. | Breaking the Game and Creating an Alternate Reality | High Rollers play Baldur's Gate 3 #2 | 57 | | Baldur's Gate III
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| 308. | All Bark and All Bite | Altheya: The Dragon Empire #35 | 57 | |
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| 309. | BIOMUTANT RPG ONE-SHOT - Episode 1 #AD | 56 | Show | Biomutant
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| 310. | High Rollers: A Rogue's Gambit #6 | The ISTAR Trials | 56 | | High Rollers
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| 311. | High Rollers: Curse of Strahd #33 - Mouth of the Beast | 56 | | High Rollers
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| 312. | High Rollers: YogCon 2019 One Shot | Wicked Wit's Wonderium! | 56 | | High Rollers
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| 313. | High Rollers: Aerois #166 | Valkyrian Vandalism | 56 | | High Rollers
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| 314. | Embers Between Friends | Altheya: The Dragon Empire #39 | 56 | |
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| 315. | Creating THE MIRE! | D&D Tasha's Cauldron Character Creation (Swarmkeeper Ranger & Spores Druid) | 56 | | World of WarCraft
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| 316. | Don't 'Google' NPC Names! | High Rollers: Aerois #shorts #dnd #dungeonsanddragons | 55 | | High Rollers
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| 317. | High Rollers: Aerois #184 | The Horrors of Hadar | 55 | | High Rollers
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| 318. | High Rollers: Lightfall's Descent #4 | Demon Deceptions | 53 | | High Rollers
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| 319. | High Rollers: Curse of Strahd #34 | Dogsbody's Revenge | 53 | | High Rollers
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| 320. | 100% Random, 100% Chaos | Pokemon Fire Red Nuzlocke #1 | 52 | | Pokémon FireRed and LeafGreen
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| 321. | High Rollers: Curse of Strahd #32 | Howls in the Night | 51 | | High Rollers
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| 322. | The Descent Into Chaos | Pokemon Fire Red Nuzlocke #2 | 49 | | Pokémon FireRed and LeafGreen
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| 323. | High Rollers: Curse of Strahd #36 | Darkness Descends | 48 | | High Rollers
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| 324. | High Rollers: One Shot | Infernal Asylum #2 | 48 | | High Rollers
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| 325. | You Scream, You Lose | Alien Isolation #1 | Chaos Twins | 48 | | Alien: Isolation
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| 326. | High Rollers: Aerois RHICAP Chapter 3 - The Road to Goldthrone (D&D Recap) | 48 | | High Rollers
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| 327. | High Rollers: Curse of Strahd #35 | The Dollmaker's Promise | 48 | | High Rollers
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| 328. | Sonic Adventure 2: Battle | CHAOS TWINS | 48 | | Sonic Adventure 2
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| 329. | Wiping out a legendary (and sentient) family of birds | High Rollers: Aerois #shorts | 47 | | High Rollers
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| 330. | High Rollers: One Shot | Honey Heist & Jason Statham's Big Vacation | 46 | | High Rollers
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| 331. | High Rollers: A Rogue's Gambit #7 | The Eye Catcher | 46 | | Idle Champions of the Forgotten Realms
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| 332. | High Rollers: Oneshot - ONE MORE QUEST #AD | 46 | | High Rollers
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| 333. | The Ashen Citadel | Altheya: The Dragon Empire #38 | 45 | |
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| 334. | Dragon Prince TTRPG: Tales of Xadia #1 w/ Role & Keep! | #AD | 45 | |
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| 335. | High Rollers: A Rogue's Gambit #8 | The Drow Who Loved Me | 44 | | Idle Champions of the Forgotten Realms
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| 336. | High Rollers Battle Royale | CHAOS TWINS | 44 | | The Sims 4
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| 337. | We Made Alien: Isolation Scarier | Chaos Twins #2 | 43 | | Alien: Isolation
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| 338. | High Rollers: Aerois #165 | Night at the Museum | 43 | | High Rollers
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| 339. | High Rollers: Curse of Strahd #20 | Dance of the Dragon | 42 | | High Rollers
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| 340. | Your chance to see High Rollers LIVE! | #shorts #dnd #highrollers | 42 | | High Rollers
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| 341. | High Rollers: Aerois RHICAP Chapter 6 - The Elenasto Fiasco (D&D Recap) | 41 | | High Rollers
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| 342. | Xmas Gifts from Wizards of the Coast and D&D Beyond! | 39 | |
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| 343. | The Most Typical RuneScape Adventure in RuneScape Kingdoms: The Roleplaying Game TTRPG! | 39 | | RuneScape
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| 344. | DM SWAP! | Jingle Jam 2022 Christmas Special | 39 | |
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| 345. | High Rollers: Oneshot - Epic Encounters: Local Legends #AD | 39 | | High Rollers
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| 346. | High Rollers: Aerois RHICAP Chapter 5 - Distant Shores (D&D Recap) | 38 | | High Rollers
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| 347. | D&D Adventures written by an AI Dungeon Master | CHAOS TWINS | 37 | | AI Dungeon
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| 348. | Beating impossible odds with Death Saving Throws in D&D! | 36 | |
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| 349. | High Rollers SPECIAL: YogCon 2019 Q&A! | 36 | | High Rollers
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| 350. | The dangers of playing D&D in real life | High Rollers: Aerois #shorts | 36 | | High Rollers
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| 351. | Chaos Twins on tour | #shorts #insomnia #highrollers | 36 | |
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| 352. | High Rollers: Rogue's Gambit #9 | The Old Windmill | 36 | | High Rollers
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| 353. | High Rollers: PAX West 2019 Q&A! | 36 | | High Rollers
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| 354. | High Rollers: Fan Art 16 May 2021 | 35 | | High Rollers
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| 355. | It's Time to Fight Back in Alien: Isolation! | Chaos Twins #3 | 34 | | Alien: Isolation
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| 356. | Tom's best joke | High Rollers: Aerois #shorts | 34 | | High Rollers
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| 357. | I whip out my 'long sword' | #shorts #dnd #highrollers | 33 | |
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| 358. | High Rollers Fan Art: 26th April 2020 | 33 | | High Rollers
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| 359. | This wasn't meant to be on the website... | #shorts #dnd #highrollers | 33 | |
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| 360. | Running From 1,000 Xenomorphs in Alien Isolation | Chaos Twins #5 (FINAL) | 33 | | Alien: Isolation
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| 361. | This dice was primed for a Nat 20! | High Rollers: Aerois #shorts | 33 | | High Rollers
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| 362. | Taking Down/Taming the AI in Alien Isolation | Chaos Twins #4 | 32 | | Alien: Isolation
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| 363. | Hardcore Training Montage | Pokemon Emerald Nuzlocke #3 | 31 | | Pokémon Emerald
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| 364. | Murge and Barf Sempsin's Grand Adventure | Divinity: Original Sin #1 | 31 | | Divinity: Original Sin
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| 365. | High Rollers LIVE at MCM Comicon 2018 | The Swift and the Sorcerous | 31 | | High Rollers
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| 366. | High Rollers & Friends play Gartic Phone! | 30 | | High Rollers
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| 367. | When the DM goes Teacher Mode on his students | #shorts #dnd #highrollers | 30 | |
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| 368. | The Rise of Jeighsun | CHAOS TWINS | 30 | |
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| 369. | High Rollers VLOG: NEW MERCH! | 30 | | High Rollers
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| 370. | Idle Champions - New Champion Qillek! #ad | 28 | | Idle Champions of the Forgotten Realms
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| 371. | When an NPC breaks down! | High Rollers: Aerois #shorts | 28 | | High Rollers
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| 372. | We Have Regrets | Pokemon Emerald Nuzlocke #10 | 28 | | Pokémon Emerald
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| 373. | High Rollers Fan Art: 8th July 2018 | 27 | | High Rollers
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| 374. | Robbin' Graves and Breakin' Webcams | Divinity: Original Sin #2 | 26 | | Divinity: Original Sin
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| 375. | DM wills a Nat One into existence | High Rollers: Aerois #shorts | 26 | | High Rollers
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| 376. | BIOMUTANT RPG ONE-SHOT - Episode 2 #AD | 26 | Show | Biomutant
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| 377. | The Fall of Jeighsun | CHAOS TWINS | 26 | | Plants vs. Zombies
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| 378. | High Rollers Cling Together! | Tactics Ogre: Reborn #ad | 25 | | Tactics Ogre: Reborn
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| 379. | We need a bigger Dice Jail... | High Rollers: Aerois #shorts | 24 | | High Rollers
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| 380. | High Rollers: Fan Art 11 October 2020 | 24 | | High Rollers
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| 381. | High Rollers Fan Art: 2nd February 2020 | 24 | | High Rollers
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| 382. | High Rollers: Xmas Special Family Boardgames! | 24 | | High Rollers
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| 383. | The worst thing to say as a Druid in D&D | #shorts #dnd #highrollers | 24 | |
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| 384. | Legendary Fishing Spot! | Pokemon Emerald Nuzlocke #2 | 23 | | Pokémon Emerald
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| 385. | This Kills the Chaos Twins | Pokemon Emerald Nuzlocke #5 | 23 | | Pokémon Emerald
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| 386. | Day of Many Deaths | Pokemon Emerald Nuzlocke #4 | 23 | | Pokémon Emerald
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| 387. | High Rollers Fan Art: 17th November 2019 | 22 | | High Rollers
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| 388. | High Rollers: Fan Art 12 July 2020 | 22 | | High Rollers
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| 389. | Befriending Cannibals by Destroying Mother Nature in The Forest | Chaos Twins | 22 | | The Forest
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| 390. | Idle Champions - New Champion Sentry! #ad | 21 | | Idle Champions of the Forgotten Realms
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| 391. | 1/160,000 chance roll in D&D | High Rollers: Aerois #shorts | 20 | | High Rollers
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| 392. | High Rollers Fan Art: 19th August 2018 | 20 | | High Rollers
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| 393. | Scottish Accent 101 | #shorts #dnd #highrollers | 20 | |
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| 394. | The Banished Pokémon | Pokemon Emerald Nuzlocke #8 | 20 | | Pokémon Emerald
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| 395. | My Alchemical Romance | High Rollers: Aerois #shorts | 20 | | High Rollers
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| 396. | Can you stealth with Wisdom? | High Rollers: Aerois #shorts | 19 | | High Rollers
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| 397. | Best NPC introduction | High Rollers: Aerois #shorts | 19 | | High Rollers
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| 398. | High Rollers Presents: RuneScape Kingdoms TTRPG w/ Jagex Mods! | 18 | | RuneScape
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| 399. | What do Bards dream of in D&D? | #shorts #dnd #highrollers | 18 | |
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| 400. | Sweet, young boy summons a giant demon of death #ttrpg #runescape | 18 | | RuneScape
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