| 1. |  GameGrumps | 597,852 | Skifree - Game Grumps | 17:14 |
| 2. | SuperMega | 206,655 | SuperMega Plays SKIFREE | 14:51 |
| 3. | LGR | 189,212 | Let's Talk Edutainment (and play the 1993 Oregon Trail) | 23:37 |
| 4. | Rick Nineg | 174,489 | Retro Games (HD) -- Ski Free----EATEN BY THE GREMLIN!! | 3:43 |
| 5. | TigerClawTV | 21,535 | SkiFree (1991 - Windows 95) | 6:50 |
| 6. | WhatZachDoes | 7,513 | The Joy Of Random Gaming - SKIFREE!!!! | 8:36 |
| 7. | Let's Play With Brigands | 6,461 | SkiFree (Who Remembers This One?) | 0:00 |
| 8. | Luke The Kook (WASD FM) | 4,550 | Attacked By Two Yetis in SkiFree! | 13:45 |
| 9. | David King | 4,127 | Ski Free - King Game Review | 3:18 |
| 10. | Manny the Headless Meme-Horse | 3,743 | Wario dies by falling off a cliff while trying to ski after Daisy hits him with a snowball.mp3 | 1:32 |
| 11. | cs188creations | 2,916 | WHAT AM I DOING? | cs188 Plays: Ski Free (1991) | 9:21 |
| 12. | Technical Bovine | 1,198 | Do you remember... SkiFree? Impressions/Commentary | 1:12 |
| 13. | GoldenFoxStream | 1,042 | GoldenFox Plays SkiFree | 26:57 |
| 14. | Grab Shiny | 860 | SkiFree | The Chill Series | 12:43 |
| 15. | Riff Arcade | 765 | Once You Win, YOU MUST SURVIVE - SkiFree | 14:12 |
| 16. | fleepy | 685 | Max Points in SkiFree? | 0:25 |
| 17. | Computer Gaming Yesterday | 383 | YouTube comes to your retro rig | SkiFree is now an RPG! | Retro PC Gaming News | 10:05 |
| 18. | DotSlashFrag | 381 | SkiFree — Let's Play A Skier's Journey | 17:44 |
| 19. | The D-Pad | 371 | Freestyle Skiing (feat. Geoff) | SkiFree | 𝗧𝗛𝗘 𝗜𝗜𝗻𝗱 𝗚𝗔𝗠𝗘𝗦 | 42:06 |
| 20. | VvvvvaVvvvvvr | 310 | Let’s Play SkiFree! Ft. Danny | 7:10 |
| 21. | iLadyCon | 299 | SKIFREE | Classic 1991 Windows Game | Full Video on Channel! #shorts | 0:38 |
| 22. | wolf397 | 255 | A Game You Barely Remember: Skifree | 14:27 |
| 23. | Jerry Young | 190 | Episode 239: Basic Type-in Programs on the Atari 8 Bit Home Computer | 1:03:54 |
| 24. | ASMR Gaming Queen & Positivity | 177 | Old School Gaming [ASMR] - Ski Free - Episode 3 | 14:25 |
| 25. | All Longplays HD | 169 | PC Longplay - SkiFree | 0:36 |
| 26. | Keep Tappin' X | 160 | Ski Free (Flash Version) | Flashback) | 12:14 |
| 27. | TenMoreMinutes | 147 | Abominable Snow Jerk - Ski Free - TenMoreMinutes | 12:41 |
| 28. | 1-UP CUP | 136 | "SkiFree Origins” | Sneaky Sasquatch | 25:18 |
| 29. | WiKi Studios | 102 | Christmas Themed Games (WiKi Gaming #42) | 14:35 |
| 30. | Dyspution Gaming | 71 | This Game Gave me Nightmares! | 0:58 |
| 31. | L0rdMasta | 63 | SkiFree | 16:25 |
| 32. | HeadphonesNeil | 61 | Zombie SkiFree | 3:58 |
| 33. | Pong Shot First | 60 | The 'I'm Gonna Play My Nintendo Switch' Stream!!! | | 3:30:54 |
| 34. | On The Branch Gaming | 59 | Skifree: Avoiding The Yeti - On the Branch Gaming | 15:26 |
| 35. | ParmaJohnIV | 55 | SkiFree! | 0:00 |
| 36. | ThePsychicGamer | 42 | Let's Play Ski Free MERRY CHRISTMAS | 6:38 |
| 37. | The Player and the Doodler | 27 | SkiFree: The Player and the Doodler | 5:06 |
| 38. | Darkening Demise | 24 | Ski Run (2600), Pure Agonizing Terror | Demise Reviews | 0:00 |
| 39. | Cyber Sorcerer | 23 | Probably Illiterate too | SkiFree | 12 Days Of Gmaer | Day 1 Ft. Ted~Cyber Sorcerer | 23:55 |
| 40. | El Conquistador Gaming | 21 | El Conquistador’s Quick Shots - Episode 4 - SkiFree | 2:39 |
| 41. | Zhobot | 19 | Windows 3.x Software Library! LET'S GET EATEN BY THE SKIFREE MONSTER! :D | 46:04 |
| 42. | Please Laugh Show | 17 | The Worst Episode (Our Greatest Mistake) - Old School Classics #1 | 11:27 |
| 43. | Travin Games | 16 | Travin Games - Skifree - We Found the Skifree Yeti! | 15:23 |
| 44. | Hugbox TGM | 14 | Hugbox Gameplays - SkiFree | 3:01 |
| 45. | TroyVsTheWorld 🕴️ | 13 | SkiFree 2: Skiier's Revenge | 0:42 |
| 46. | RobotSquid | 13 | Ski free: Old School Style | 6:01 |
| 47. | Raccoon Republic | 11 | The Problem with "Big" Games | 15:06 |
| 48. | Fke | 10 | SkiFree (1991) | 4:09 |
| 49. | No More Lines | 10 | Ski Free | 7:15 |
| 50. | dishamonpow | 8 | Dish Streams - SkiFree | 4:40 |
| 51. | Weird Gamer89 | 5 | SkiFree HIDDEN GEM | 1:20 |
| 52. | CrazyVikingGamer | 4 | SkiFree - Gameplay | 0:00 |
