| 1. | Here Comes Pacman but there's no Pacman | 545 | |
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| 2. | charliewinsmore on the rajjpatel show | 74 | Show |
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| 3. | charliewinsmore -- the henry's baseball saga 2 | 70 | |
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| 4. | charliewinsmore -- the henry's baseball saga | 68 | |
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| 5. | CHARLIEWINSMORE - Teaser Trailer | 59 | |
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| 6. | CHARLIEWINSMORE BEST OF 2022 | 58 | |
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| 7. | charliewinsmore -- the henry's baseball saga 3 | 52 | |
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| 8. | charliewinsmore -- Best of the Dreamcast | 43 | | Dragonriders: Chronicles of Pern
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| 9. | charliewinsmore songs continued by an AI (Open AI Jukebox) | 38 | |
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| 10. | CHARLIEWINSMORE BEST OF 2020 | 37 | |
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| 11. | the lyrical genius of charliewinsmore | 35 | |
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| 12. | charliewinsmore -- spiritual streamers | 31 | |
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| 13. | charliewinsmore -- henry's baseball responds | 30 | | Tiger Woods PGA Tour 2005
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| 14. | charliewinsmore -- The Great Pog Wars (5/31/2020) | 28 | | Poly Bridge 2
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| 15. | charliewinsmore -- the henry's baseball rap | 28 | |
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| 16. | charliewinsmore -- irl stream highlights | 26 | |
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| 17. | charliewinsmore -- computer hell | 25 | |
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| 18. | charliewinsmore -- the tabletop conspiracy of 2017 | 25 | |
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| 19. | charliewinsmore -- the chamone saga ep 14: Officer Wrong | 25 | | Grand Theft Auto V
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| 20. | charliewinsmore -- The Making of "Creed - Get That Goblin" | 24 | | Hydroneer
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| 21. | charliewinsmore -- "Shenmue Saturday -- Beginning Again" (2015) | 23 | | Shenmue
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| 22. | charliewinsmore -- japanese cooking 101 | 23 | |
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| 23. | charliewinsmore -- charlie explores cookie town world | 22 | |
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| 24. | charliewinsmore -- gold wife | 22 | |
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| 25. | charliewinsmore -- twitch sings | 20 | | Twitch Sings
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| 26. | charliewinsmore -- lego rap | 20 | |
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| 27. | charliewinsmore -- clock boy ride | 20 | | Planet Coaster
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| 28. | charliewinsmore -- watching old videos | 18 | |
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| 29. | charliewinsmore -- The Sims 3: RISEN PAPI | 18 | | The Sims 3
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| 30. | charliewinsmore -- oppa winsmore style | 18 | |
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| 31. | charliewinsmore -- the chamone saga ep 1 | 18 | | Grand Theft Auto V
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| 32. | THE 1ST ANNUAL WINSMORE AWARDS | 18 | |
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| 33. | charliewinsmore -- the chamone saga ep 4: Annie May | 17 | | Grand Theft Auto V
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| 34. | CHUCKTUTS -- HOW TO MAKE A MOVIE FROM SCRATCH | 17 | Tutorial |
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| 35. | charliewinsmore -- seinfeld fart coaster | 17 | | Planet Coaster
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| 36. | charliewinsmore -- tony hawk knock-offs | 16 | |
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| 37. | The Department of Horticulture - SWAGGER MATH MACHINE [Full Album] | 16 | |
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| 38. | charliewinsmore -- LOLLITUNE (Official Video) | 16 | |
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| 39. | charliewinsmore -- gambling addict plays real slots | 16 | | Cleopatra Fortune
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| 40. | CHARLIEWINSMORE BEST OF 2021 | 16 | | Grand Theft Auto V
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| 41. | charliewinsmore -- The Bitcoin Bandit (Internet Cafe Simulator) | 16 | | Internet Cafe Simulator
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| 42. | charliewinsmore -- Cooking Stream (4/19/2018) | 16 | |
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| 43. | charliewinsmore -- the chamone saga ep 13: Restraining Order | 16 | | Grand Theft Auto V
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| 44. | Charlie Winsmore - BACKYARD BASEBALL RAP (VIDEO GAME RAP PARODY) | 16 | |
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| 45. | charliewinsmore -- my boyfriend 2 | 15 | | My Boyfriend
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| 46. | charliewinsmore -- the chamone saga ep 16: Glitch in the Matrix | 15 | | Grand Theft Auto V
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| 47. | charliewinsmore -- ant coaster | 15 | | Planet Coaster
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| 48. | charliewinsmore -- Android Games | 15 | |
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| 49. | charliewinsmore -- twitch sings 2 | 14 | | Twitch Sings
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| 50. | charliewinsmore -- H1Z1: The Cranberry Killer (1/16/2015) | 14 | | Just Survive
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| 51. | charliewinsmore -- Entropia: Voyage to Club NEVERDIE | 14 | | Entropia Universe
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| 52. | charliewinsmore -- gambling stream w/ chat (3/10/2021) | 14 | |
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| 53. | charliewinsmore -- cookie town world: the ride | 14 | | Planet Coaster
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| 54. | charliewinsmore -- Kenshi Comeback | 13 | | Kenshi
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| 55. | charliewinsmore -- the chamone saga ep 18: Fingle Gets His Name | 13 | | Grand Theft Auto V
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| 56. | charliewinsmore -- chat asks for chatter | 13 | | Backyard Baseball 2004
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| 57. | charliewinsmore -- the chamone saga ep 17: A Lesson in Equality | 13 | | Grand Theft Auto V
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| 58. | charliewinsmore -- The Sims 3: Risen Papi RELOADED | 13 | | The Sims 3
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| 59. | charliewinsmore -- Winsmore Simulator (Streamer Daily) | 13 | | Streamer Daily
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| 60. | charliewinsmore -- newgrounds games & conspiracy videos (10/01/2018) | 13 | |
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| 61. | ELECTRIC ENERGY DRINK | 13 | |
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| 62. | charliewinsmore -- Shenmue: Highlights (2015) | 13 | | Shenmue
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| 63. | charliewinsmore -- the chamone saga ep 15: A New Face in Town | 12 | | Grand Theft Auto V
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| 64. | charliewinsmore -- the lard gaming entertainment saga | 11 | |
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| 65. | charliewinsmore -- The Sims 4: Don Smith's Massacre | 11 | | The Sims 4
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| 66. | charliewinsmore -- the chamone saga ep 8: New Server, New Chamone | 11 | | Grand Theft Auto V
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| 67. | charliewinsmore -- thechief1114's big donation | 11 | | Grand Theft Auto V
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| 68. | charliewinsmore -- the chamone saga ep 6: Head-on Collision | 10 | | Grand Theft Auto V
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| 69. | charliewinsmore -- bee coaster | 10 | | Planet Coaster
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| 70. | charliewinsmore -- the chamone saga ep 11: BarP | 10 | | Grand Theft Auto V
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| 71. | charliewinsmore -- The Crungler Stream (November 2015) | 10 | | The Sims 3
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| 72. | charliewinsmore -- dragon ride | 10 | | Planet Coaster
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| 73. | charliewinsmore -- nicki minaj: the empire | 10 | |
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| 74. | TIME INVASION | 10 | |
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| 75. | charliewinsmore -- super seducer | 10 | | Super Seducer
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| 76. | charliewinsmore -- po box fanmail 5: the final unboxing | 9 | |
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| 77. | charliewinsmore -- po box fanmail 2: son of mail | 9 | |
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| 78. | charliewinsmore -- grass mountain | 9 | | Planet Coaster
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| 79. | charliewinsmore -- the chamone saga ep 12: Premeditated Murder Trial | 9 | | Grand Theft Auto V
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| 80. | charliewinsmore -- "Shenmue -- CAN OPENING RISTAR GIVEAWAY EVERY 100K FOLLOWS" (2015) | 9 | | Shenmue
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| 81. | charliewinsmore -- phantasmagoria 2 (full stream) | 9 | | Phantasmagoria: A Puzzle of Flesh
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| 82. | charliewinsmore -- Wrestling Empire: Weak Bone Man Rises | 9 | | Wrestling Empire
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| 83. | charliewinsmore -- city of fools & velvet sundown (full stream) | 9 | |
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| 84. | charliewinsmore -- Winsmore's Awesome Houses Done Quick (September 2018) | 9 | | The Sims 4
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| 85. | charliewinsmore -- po box fanmail 4: christmas edition | 9 | |
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| 86. | charliewinsmore -- the chamone saga ep 19: TIME BIRD | 8 | | Grand Theft Auto V
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| 87. | charliewinsmore -- the chamone saga ep 2: Profiling | 8 | | Grand Theft Auto V
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| 88. | charliewinsmore -- Super Mario Maker 2: Super Expert | 8 | | Super Mario Maker 2
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| 89. | charliewinsmore -- "it's time for another 2022 stream" VOD w/ chat (1/13/22) | 8 | | Star Wars Galaxies
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| 90. | charliewinsmore -- the chamone saga ep 10: Partners in EMS | 8 | | Grand Theft Auto V
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| 91. | charliewinsmore -- bill gate diss (music video) | 8 | |
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| 92. | charliewinsmore -- the chamone saga ep 9: Health & Safety Concerns | 8 | | Grand Theft Auto V
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| 93. | charliewinsmore -- the chamone saga ep 7: Chamone Dies | 8 | | Grand Theft Auto V
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| 94. | charliewinsmore -- po box fanmail 3: revenge of the mayo | 8 | |
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| 95. | charliewinsmore -- japan crate (2016) | 7 | |
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| 96. | charliewinsmore -- po box fanmail | 7 | |
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| 97. | charliewinsmore -- the chamone saga ep 3: Better Phone Chamone | 7 | | Grand Theft Auto V
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| 98. | charliewinsmore -- "SHENMUE CONTINUED" (2015) | 7 | | Shenmue
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| 99. | charliewinsmore -- Fallout: New Vegas & COD Mobile stream w/ chat (2/14/2021) | 7 | | Fallout: New Vegas
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| 100. | charliewinsmore -- star wars galaxies stream | 7 | | Star Wars Galaxies
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