| 1. | Here Comes Pacman but there's no Pacman | 6,480 | |
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| 2. | CHARLIEWINSMORE - Teaser Trailer | 379 | |
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| 3. | charliewinsmore on the rajjpatel show | 322 | Show |
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| 4. | charliewinsmore -- computer hell | 289 | |
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| 5. | charliewinsmore -- the henry's baseball saga | 280 | |
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| 6. | the lyrical genius of charliewinsmore | 246 | |
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| 7. | charliewinsmore -- Best of the Dreamcast | 241 | | Dragonriders: Chronicles of Pern
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| 8. | charliewinsmore -- clock boy ride | 235 | | Planet Coaster
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| 9. | CHARLIEWINSMORE BEST OF 2020 | 234 | |
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| 10. | charliewinsmore -- The Making of "Creed - Get That Goblin" | 231 | | Hydroneer
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| 11. | charliewinsmore -- seinfeld fart coaster | 225 | | Planet Coaster
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| 12. | CHARLIEWINSMORE BEST OF 2022 | 270 | |
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| 13. | charliewinsmore -- charlie explores cookie town world | 208 | |
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| 14. | charliewinsmore -- Entropia: Voyage to Club NEVERDIE | 204 | | Entropia Universe
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| 15. | charliewinsmore -- the tabletop conspiracy of 2017 | 196 | |
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| 16. | charliewinsmore -- lego rap | 183 | |
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| 17. | charliewinsmore -- gold wife | 175 | |
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| 18. | charliewinsmore -- spiritual streamers | 175 | |
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| 19. | charliewinsmore -- the henry's baseball saga 2 | 173 | |
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| 20. | charliewinsmore -- the henry's baseball saga 3 | 164 | |
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| 21. | charliewinsmore -- cookie town world: the ride | 161 | | Planet Coaster
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| 22. | charliewinsmore -- the henry's baseball rap | 159 | |
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| 23. | Charlie Winsmore - BACKYARD BASEBALL RAP (VIDEO GAME RAP PARODY) | 157 | |
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| 24. | charliewinsmore -- thechief1114's big donation | 154 | | Grand Theft Auto V
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| 25. | charliewinsmore -- super seducer | 152 | | Super Seducer
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| 26. | CHARLIEWINSMORE BEST OF 2021 | 157 | | Grand Theft Auto V
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| 27. | charliewinsmore -- ant coaster | 142 | | Planet Coaster
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| 28. | charliewinsmore -- The Bitcoin Bandit (Internet Cafe Simulator) | 141 | | Internet Cafe Simulator
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| 29. | charliewinsmore -- the chamone saga ep 1 | 137 | | Grand Theft Auto V
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| 30. | charliewinsmore -- Winsmore Simulator (Streamer Daily) | 133 | | Streamer Daily
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| 31. | charliewinsmore -- The Sims 4: Don Smith's Massacre | 132 | | The Sims 4
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| 32. | charliewinsmore -- oppa winsmore style | 130 | |
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| 33. | charliewinsmore -- japanese cooking 101 | 123 | |
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| 34. | charliewinsmore -- watching old videos | 123 | |
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| 35. | charliewinsmore -- irl stream highlights | 119 | |
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| 36. | charliewinsmore -- bill gate diss (music video) | 130 | |
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| 37. | charliewinsmore -- the lard gaming entertainment saga | 116 | |
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| 38. | charliewinsmore -- Android Games | 115 | |
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| 39. | ELECTRIC ENERGY DRINK | 114 | |
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| 40. | charliewinsmore -- twitch sings | 113 | | Twitch Sings
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| 41. | charliewinsmore -- LOLLITUNE (Official Video) | 148 | |
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| 42. | charliewinsmore -- The Great Pog Wars (5/31/2020) | 110 | | Poly Bridge 2
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| 43. | charliewinsmore -- bee coaster | 115 | | Planet Coaster
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| 44. | charliewinsmore -- grass mountain | 109 | | Planet Coaster
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| 45. | TIME INVASION | 109 | |
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| 46. | charliewinsmore songs continued by an AI (Open AI Jukebox) | 105 | |
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| 47. | charliewinsmore -- twitch sings 2 | 102 | | Twitch Sings
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| 48. | charliewinsmore -- *eats doritos off screen* | 101 | |
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| 49. | charliewinsmore -- a kickstarter classic | 101 | |
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| 50. | charliewinsmore -- tony hawk knock-offs | 98 | |
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| 51. | charliewinsmore -- The Sims 3: RISEN PAPI | 99 | | The Sims 3
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| 52. | charliewinsmore -- the chamone saga ep 2: Profiling | 95 | | Grand Theft Auto V
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| 53. | THE 1ST ANNUAL WINSMORE AWARDS | 94 | |
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| 54. | Owl City - Fireflies (Adly91 Reupload) | 88 | |
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| 55. | charliewinsmore -- gambling addict plays real slots | 86 | | Cleopatra Fortune
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| 56. | charliewinsmore -- nicki minaj: the empire | 85 | |
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| 57. | charliewinsmore -- my ass: the ride | 83 | | Planet Coaster
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| 58. | charliewinsmore -- the chamone saga ep 3: Better Phone Chamone | 81 | | Grand Theft Auto V
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| 59. | The Department of Horticulture - SWAGGER MATH MACHINE [Full Album] | 80 | |
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| 60. | charliewinsmore -- po box fanmail 2: son of mail | 79 | |
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| 61. | charliewinsmore -- the mask: the ride | 77 | | Planet Coaster
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| 62. | charliewinsmore -- dragon ride | 76 | | Planet Coaster
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| 63. | charliewinsmore -- Wrestling Empire: Weak Bone Man Rises | 74 | | Wrestling Empire
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| 64. | charliewinsmore -- the chamone saga ep 4: Annie May | 74 | | Grand Theft Auto V
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| 65. | charliewinsmore -- the chamone saga ep 12: Premeditated Murder Trial | 73 | | Grand Theft Auto V
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| 66. | charliewinsmore -- Kenshi Comeback | 73 | | Kenshi
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| 67. | charliewinsmore -- the chamone saga ep 16: Glitch in the Matrix | 71 | | Grand Theft Auto V
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| 68. | charliewinsmore -- the chamone saga ep 19: TIME BIRD | 68 | | Grand Theft Auto V
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| 69. | charliewinsmore -- the chamone saga ep 18: Fingle Gets His Name | 67 | | Grand Theft Auto V
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| 70. | charliewinsmore -- the chamone saga ep 17: A Lesson in Equality | 67 | | Grand Theft Auto V
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| 71. | charliewinsmore -- po box fanmail 4: christmas edition | 67 | |
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| 72. | charliewinsmore -- the chamone saga ep 5: Multiple Personalities | 64 | | Grand Theft Auto V
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| 73. | CHUCKTUTS -- HOW TO MAKE A MOVIE FROM SCRATCH | 64 | Tutorial |
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| 74. | charliewinsmore -- po box fanmail 3: revenge of the mayo | 63 | |
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| 75. | rare charliewinsmore cobbler freestyle | 61 | |
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| 76. | charliewinsmore -- the chamone saga ep 8: New Server, New Chamone | 61 | | Grand Theft Auto V
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| 77. | charliewinsmore -- caitlyn jenner voice | 61 | |
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| 78. | charliewinsmore -- backwards cover stream 1 (all star, lose yourself, mad world) | 60 | |
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| 79. | charliewinsmore -- po box fanmail 5: the final unboxing | 60 | |
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| 80. | charliewinsmore -- tim's american hellscape | 60 | | Planet Coaster
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| 81. | charliewinsmore -- the chamone saga ep 9: Health & Safety Concerns | 59 | | Grand Theft Auto V
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| 82. | charliewinsmore -- the chamone saga ep 13: Restraining Order | 59 | | Grand Theft Auto V
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| 83. | charliewinsmore -- the chamone saga ep 15: A New Face in Town | 59 | | Grand Theft Auto V
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| 84. | charliewinsmore -- Super Mario Maker 2: Super Expert | 58 | | Super Mario Maker 2
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| 85. | charliewinsmore -- christmas ride | 57 | | Planet Coaster
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| 86. | charliewinsmore -- po box fanmail | 57 | |
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| 87. | charliewinsmore -- henry's baseball responds | 56 | | Tiger Woods PGA Tour 2005
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| 88. | charliewinsmore -- the chamone saga ep 7: Chamone Dies | 56 | | Grand Theft Auto V
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| 89. | charliewinsmore -- The Sims 3: Risen Papi RELOADED | 58 | | The Sims 3
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| 90. | charliewinsmore -- the chamone saga ep 14: Officer Wrong | 55 | | Grand Theft Auto V
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| 91. | charliewinsmore -- my boyfriend 2 | 54 | | My Boyfriend
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| 92. | charliewinsmore -- jumpix reloaded | 54 | | Planet Coaster
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| 93. | charliewinsmore -- chat asks for chatter | 52 | | Backyard Baseball 2004
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| 94. | charliewinsmore -- Shenmue: Highlights (2015) | 52 | | Shenmue
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| 95. | charliewinsmore -- the chamone saga ep 10: Partners in EMS | 52 | | Grand Theft Auto V
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| 96. | charliewinsmore -- rare shenmue freestyle | 51 | | Shenmue
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| 97. | charliewinsmore -- dalt wisney's descent | 51 | | Planet Coaster
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| 98. | charliewinsmore -- witch house | 50 | | Planet Coaster
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| 99. | charliewinsmore -- city of fools & velvet sundown (full stream) | 50 | |
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| 100. | charliewinsmore -- the chamone saga ep 11: BarP | 48 | | Grand Theft Auto V
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