| 301. | Random DOS Game Show #697: Izmir (1995) | 24 | |
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| 302. | Randon DOS Game Show #694: Gunhed (1994) | 24 | |
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| 303. | Random DOS Game Show #586: Power Drive (1995) | 24 | |
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| 304. | Random DOS Game Show #536: Lure of the Temptress (1992) | 24 | | Lemmings
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| 305. | Random DOS Game Show #721: Fantasy General (1996) | 24 | | Fantasy General
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| 306. | Random DOS Game Show #772: Xenoball (1995) | 24 | |
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| 307. | Random DOS Game Show #312: In Pursuit of Greed (1995) | 24 | | Star Wars Jedi Knight: Dark Forces II
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| 308. | Random DOS Game Show #581: Capitalism (1995) | 24 | |
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| 309. | James Randomly Talks About... Centurion: Defender of Rome (1990) | 24 | | Centurion: Defender of Rome
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| 310. | Random DOS Game Show #768: Hoser (1982) | 24 | | Duke Nukem 3D
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| 311. | Croina VS FPS #12: Operation Bodycount (1994) | 24 | | Operation Body Count
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| 312. | Random DOS Game Show #763: Sid Meier's Colonization (1994) | 24 | | Sid Meier's Colonization
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| 313. | Random DOS Game Show #737: Oligopoly (1987) | 24 | |
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| 314. | Random DOS Game Show #622: Tsumera (1996) | 23 | Show |
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| 315. | Random DOS Game Show #667: Boom (1994) | 23 | | Pac-Man
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| 316. | Random DOS Game Show Special: Arrakis (1997) | 23 | |
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| 317. | James Randomly Talks About... Star Trek: The Next Generation - A Final Unity (1995) | 23 | | Star Trek: The Next Generation
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| 318. | Random DOS Game Show #871: Pac (1992) | 23 | | Pac-Man
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| 319. | Random DOS Game Show #938: Tournament Tennis (1985) | 25 | | Super Tennis
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| 320. | Random DOS Game Show #715: Lighthouse: The Dark Being (1996) | 23 | | Lighthouse: The Dark Being
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| 321. | Random DOS Game Show Special: Top 25 Random DOS Games I've Enjoyed So Far (Part 1) | 23 | | Star Wars Jedi Knight: Dark Forces II
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| 322. | Random DOS Game Show #689: Rodney's Funscreen (1992) | 23 | | Lemmings
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| 323. | Channel Update - July 2021 | 23 | |
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| 324. | Random DOS Game Show #402: Jurassic Park (1993) | 23 | | Lemmings
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| 325. | Random DOS Game Show #669: Kaos (1998) | 23 | | Doom
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| 326. | 10 of the Best: Expansion Packs (1995-2010) | 23 | | Diablo II
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| 327. | Random DOS Game Show #550: Black Sect (1993) | 23 | |
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| 328. | Random DOS Game Show #603: Eliza (1966) | 23 | Show | Lemmings
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| 329. | Random DOS Game Show #643: Speedball (1988) | 23 | Show | Speedball
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| 330. | Random DOS Game Show #713: Hack (1984) | 23 | |
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| 331. | Random DOS Game Show #827: Tommy's Gorilla Ball Babies (1987) | 23 | |
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| 332. | Random DOS Game Show #648: Sigil (2019) | 23 | Show | Doom
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| 333. | Random DOS Game Show #505: The Terminator 2029 (1992) | 23 | | The Terminator 2029
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| 334. | Random DOS Game Show #424: Indiana Jones and the Last Crusade (the action game) (1989) | 23 | |
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| 335. | Random DOS Game Show 935: Crystal Ball (1988) | 28 | |
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| 336. | Random DOS Game Show #687: Myman (2000) | 23 | | Pac-Man
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| 337. | Random DOS Game Show #630: Metal Gear (1990) | 23 | | Metal Gear
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| 338. | Random DOS Game Show #546: Buck Rogers: Countdown to Doomsday (1990) | 23 | | Buck Rogers: Countdown to Doomsday
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| 339. | Random DOS Game Show #558: Dangerous Dave's Risky Rescue (1993) | 23 | | Dangerous Dave's Risky Rescue
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| 340. | Random DOS Game Show #954: Elephant Herding (2015) | 24 | | Doom II: Hell on Earth
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| 341. | Random DOS Game Show #79: Hacx: Twitch 'n Kill (1997) | 23 | | Star Wars Jedi Knight: Dark Forces II
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| 342. | Random DOS Game Show #638: CHAMP Ms. Pac-Em (1996) | 23 | |
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| 343. | Random DOS Game Show #754: Mie (1989) | 23 | |
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| 344. | Random DOS Game Show #849: Taco Bell: Tasty Temple Challenge (2000) | 24 | |
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| 345. | Random DOS Game Show #797: Color Buster (1992) | 23 | |
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| 346. | Random DOS Game Show #750: Air-Strike (1998) | 23 | | Action 52
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| 347. | Random DOS Game Show #651: Microsoft Flight Simulator 1.0 (1982) | 23 | | Microsoft Flight Simulator 1.0
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| 348. | Random DOS Game Show #490: Siege (1992) | 22 | |
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| 349. | Channel Update: 1,000 Subscribers & Patreon | 22 | Vlog |
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| 350. | Random DOS Game Show #735: Red Sky At Morning (1993) | 22 | |
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| 351. | Random DOS Game Show #621: Commander Keen 2: The Earth Explodes (1990) | 22 | | Commander Keen in Invasion of the Vorticons
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| 352. | Random DOS Game Show #596: Around The World In 80 Days (1994) | 22 | | Doom
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| 353. | Random DOS Game Show #911: A Tribute to Tetris (1995) | 22 | | Tetris
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| 354. | Random DOS Game Show #617: Warlords II Deluxe (1995) | 22 | | Warlords II
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| 355. | Random DOS Game Show #732: Tommy's Antfarm (1986) | 22 | | Pac-Man
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| 356. | Random DOS Game Show #712: True Blood (1994) | 22 | |
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| 357. | Random DOS Game Show #821: Maximum Roadkill (1995) | 22 | | Slipstream 5000
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| 358. | Random DOS Game Show #620: Dream Warrior (1989) | 22 | | Dream Warrior
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| 359. | Random DOS Game Show #583: They Call Me... The Skul (1996) | 22 | | They Call Me... The Skul
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| 360. | Random DOS Game Show #944: A Question of Sport (1988) | 23 | | A Question of Sport
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| 361. | James Randomly Talks About... Dune (1992) | 22 | |
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| 362. | Random DOS Game Show #905: Prison Amok (1997) | 27 | |
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| 363. | Random DOS Game Show #876: Willy the Worm (1985) | 22 | | Willy the Worm
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| 364. | Random DOS Game Show #900: Dedale (1986) | 24 | | Doom II: Hell on Earth
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| 365. | Random DOS Game Show #526: Xerix II (1994) | 22 | |
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| 366. | Random DOS Game Show #805: Congo Bongo (1984) | 22 | | Congo Bongo
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| 367. | Random DOS Game Show #595: Encounter (1984) | 22 | |
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| 368. | Random DOS Game Show #559: Eradicator (1996) | 22 | Show | Doom
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| 369. | Random DOS Game Show #753: Football Limited (1994) | 22 | Show | Football Limited
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| 370. | Random DOS Game Show #345: Nova 9 (1991) | 22 | |
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| 371. | Random DOS Game Show #500: Awesome Earl In: SkateRock (1988) | 22 | Show | Lemmings
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| 372. | Random DOS Game Show #542: Yacht Racing Simulator (1986) | 22 | |
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| 373. | Random DOS Game Show #640: The American Challenge: A Sailing Simulation (1986) | 22 | | American Challenge: A Sailing Simulation
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| 374. | Random DOS Game Show #818: SimRefinery (1992) | 22 | | SimRefinery
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| 375. | Random DOS Game Show #540: Star Command: Revolution (1997) | 22 | | Star Command: Revolution
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| 376. | Subscriber Spotlight #4 - Spooky Scary Subscribers! | 22 | |
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| 377. | Random DOS Game Show #594: Bad Street Brawler (1987) | 22 | | Bad Street Brawler
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| 378. | TIE Fighter Total Conversion Social Media Update! | 22 | |
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| 379. | Random DOS Game Show #469: Catacomb 3-D (1991) | 22 | | Catacomb 3-D
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| 380. | Random DOS Game Show #948: Paganitzu (1991) | 28 | | Paganitzu
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| 381. | Random DOS Game Show #764: Bubble Ghost (1988) | 22 | | Bubble Ghost
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| 382. | Random DOS Game Show #727: Yo! Joe! (1993) | 22 | |
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| 383. | Random DOS Game Show #943: Blur Way / Unmyeong-ui Gyeoljeon (1995) | 26 | |
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| 384. | GuyMod - A Star Wars: TIE Fighter mod for XWVM, TFVM & TFTC | 22 | | Star Wars: TIE Fighter
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| 385. | Random DOS Game Show #808: Alien River (2017) | 22 | |
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| 386. | Random DOS Game Show #313: Comanche: Maximum Overkill (1992) | 22 | | Star Wars Jedi Knight: Dark Forces II
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| 387. | Random DOS Game Show #627: Rage Against The Machine (1997) | 21 | |
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| 388. | Random DOS Game Show #695: 16 (1996) | 21 | Show | Pac-Man
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| 389. | Random DOS Game Show #383: Warcraft: Orcs & Humans (1994) | 21 | | WarCraft: Orcs & Humans
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| 390. | Random DOS Game Show #893: Sabotaje (1988) | 27 | | Doom II: Hell on Earth
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| 391. | Random DOS Game Show #752: 20th Century Frog (1988) | 21 | |
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| 392. | Random DOS Game Show #932: GobMan (1992) | 32 | |
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| 393. | Random DOS Game Show #610: Spirit of Adventure (1991) | 21 | | Spirit of Adventure
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| 394. | Random DOS Game Show #428: Alien Incident (1996) | 21 | Show | Alien Incident
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| 395. | Random DOS Game Show #701: SimAnt (1991) | 21 | | SimAnt
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| 396. | Random DOS Game Show #329: Castles (1991) | 21 | | Ultima VII: The Black Gate
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| 397. | Random DOS Game Show #788: Alpha Build (1986) | 21 | Let's Play |
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| 398. | Random DOS Game Show #281: Demon Stalkers: The Raid on Doomfane (1987) | 21 | | Demon Stalkers
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| 399. | Random DOS Game Show #488: Secret Mission (1996) | 21 | Show |
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| 400. | Random DOS Game Show #774: Brix 3: Superlogic (1993) | 21 | | Brix
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