| 2024-04-16 | Drawing 100 Garfields From Memory in 100 minutes | 26:57 | 48,896 | |
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| 2024-04-11 | Four Drawing Challenges We Missed Last Time | 58:44 | 200,494 | |
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| 2024-04-09 | Drawing the Weirdest SCPs (That We've Never Heard Of Before) | 48:59 | 199,311 | |
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| 2024-04-04 | Turning The Most Weirdly Specific T-Shirts Into Characters | 41:55 | 159,802 | |
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| 2024-04-02 | Drawing Characters Using a Cats 2019 Name Generator | 40:28 | 165,610 | |
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| 2024-04-01 | Dancing Berries - MORNING DRAWFEE | 8:08 | 95,792 | |
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| 2024-03-28 | Drawing NEW Characters for the Elden Ring DLC | 44:07 | 160,569 | | Elden Ring
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| 2024-03-26 | 10 Years of Drawfee | 53:09 | 180,285 | |
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| 2024-03-21 | Drawing Characters Based on Pasta Names | 35:49 | 146,644 | |
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| 2024-03-19 | Guessing Julia's Human Versions of Cartoon Characters (Impossible) | 45:36 | 307,574 | |
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| 2024-03-14 | Drawing Characters That Would Say These Randomly Generated Catchphrases | 44:17 | 184,523 | |
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| 2024-03-12 | Drawing the Weirdest Yakuza Characters (That We've Never Seen Before) | 43:39 | 164,346 | |
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| 2024-03-07 | Opposite Characters Drawing CHALLENGE | 23:12 | 163,077 | |
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| 2024-03-05 | Making Up Classic Book Plots Based Only on the Titles | 43:55 | 189,492 | |
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| 2024-02-29 | Drawing Japanese Folklore Creatures Based Only on Description | 35:42 | 199,292 | |
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| 2024-02-27 | Guessing Julia's Characters From Memory (And Drawing Fan Art of Them) | 1:01:28 | 312,947 | |
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| 2024-02-22 | Professional Artists Redraw MORE of Their Childhood Art | 44:58 | 254,461 | |
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| 2024-02-20 | Drawing Pokémon Type Combos that were NEVER USED IN GAME | 40:56 | 207,950 | |
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| 2024-02-15 | Drawing "Joker Memes" Based Only on the Text | 40:55 | 210,854 | |
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| 2024-02-13 | Using Animal Face Proportions to Make HUMAN Faces | 31:57 | 223,656 | |
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| 2024-02-08 | Cloud Shapes Drawing CHALLENGE | 49:49 | 185,333 | |
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| 2024-02-06 | Illustrating the Weirdest Internet Ads We Can Find | 37:39 | 190,579 | |
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| 2024-02-01 | Turning Three Random Emojis Into ART | 43:28 | 215,472 | |
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| 2024-01-30 | Drawing What We Think These Weird Product Reviews are About | 39:49 | 210,858 | Review |
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| 2024-01-25 | Drawing the Wielders of Randomly Generated Magical Weapons | 56:44 | 341,472 | |
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| 2024-01-23 | We're Just Drawing Little Guys Today | 56:27 | 240,426 | |
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| 2024-01-18 | One Character, SIX Drawing Challenges | 1:21:26 | 375,026 | |
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| 2024-01-16 | Turning Animals Into Human Characters CHALLENGE | 36:04 | 194,287 | |
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| 2024-01-11 | Drawing using Name Generators from the Ancient Internet | 49:18 | 277,175 | |
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| 2024-01-09 | Making New Characters out of Bizarre Food Names | 43:22 | 198,334 | |
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| 2024-01-04 | Turning Awful Cartoon Character Ice Cream BACK Into Cartoons Again | 32:32 | 197,933 | |
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| 2024-01-02 | Drawing Our New Year's Resolutions for 2024 | 44:32 | 206,128 | |
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| 2023-12-26 | Drawfee's Favorite Moments of 2023 | 32:14 | 255,717 | |
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| 2023-12-14 | Drawing Each Other Gifts for the Holiday Season! | 45:08 | 251,499 | |
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| 2023-12-12 | Cookie Cutter Shape Drawing CHALLENGE | 39:59 | 214,659 | |
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| 2023-12-07 | Nathan's BROTHER Challenged Him to a Speed Draw Contest... | 39:27 | 226,994 | |
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| 2023-12-05 | Adding a Second Panel to Heathcliff Comics | 25:46 | 173,842 | |
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| 2023-11-30 | Drawing the Weirdest Local News Headlines | 46:23 | 225,765 | |
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| 2023-11-28 | Name Acronym Drawing CHALLENGE | 37:16 | 212,817 | |
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| 2023-11-21 | Drawing What We're Thankful For in 2023 | 42:27 | 186,862 | |
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| 2023-11-16 | Putting Garfield BACK Into Garfield Minus Garfield | 34:43 | 261,975 | | Garfield
|
| 2023-11-14 | Making Characters out of Gemstone Names | 35:51 | 183,428 | |
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| 2023-11-10 | Here’s What You Missed Last Time on Drawfee | 1:20 | 109,023 | |
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| 2023-11-09 | Redesigning Our Least Favorite Pokémon | 49:00 | 330,359 | |
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| 2023-11-07 | Making NEW Drawings out of OLD Drawings' Silhouettes | 53:30 | 259,928 | |
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| 2023-11-02 | Doing a 30 Day Drawing Challenge in 30 Minutes | 41:23 | 192,347 | |
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| 2023-10-31 | Turning Awful 2 Sentence Horror Stories Into Illustrations | 43:13 | 265,493 | | Horror Stories
|
| 2023-10-26 | Making Cryptids for our Own Hometowns | 48:11 | 238,763 | |
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| 2023-10-24 | Artists Draw Fan Art of Their Favorite Niche Media | 38:34 | 184,875 | |
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| 2023-10-19 | Drawing Anime Characters that have Zero Google Results | 44:38 | 217,858 | |
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| 2023-10-17 | The Return of the Random Shape Challenge | 40:10 | 182,873 | |
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| 2023-10-12 | Making Characters out of a Professional VA's Voices | 45:00 | 186,669 | |
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| 2023-10-10 | Drawing Celebrities Based Only on Their Vibes | 51:41 | 184,094 | |
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| 2023-10-05 | Designing D&D Characters Using Randomly Generated Traits | 30:17 | 185,698 | |
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| 2023-10-03 | Drawing Anime Characters Based Only on Their Powers | 46:14 | 223,192 | |
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| 2023-09-28 | Drawing Randomly Generated Fantasy Classes | 29:37 | 172,775 | |
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| 2023-09-26 | Drawing More Randomly Generated Inspirational Posters | 34:05 | 217,404 | |
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| 2023-09-21 | Making New Pokémon out of Their Original Names | 50:24 | 223,630 | |
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| 2023-09-19 | Drawing What's Outside of Famous Album Covers | 38:20 | 220,482 | |
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| 2023-09-14 | Drawing the Origins of the Weirdest Laws in America | 34:19 | 187,653 | |
|
| 2023-09-12 | We Typed on our Phones Without Looking and Had to Draw the Result | 1:00:26 | 282,521 | |
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| 2023-09-07 | Making Mascots for the Weirdest Holidays We Could Find | 35:29 | 178,586 | |
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| 2023-09-05 | Four Artists, One Manga Page CHALLENGE | 55:47 | 249,490 | |
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| 2023-08-31 | Turning Random Lines of Action into Characters | 38:17 | 251,279 | |
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| 2023-08-29 | Drawing What We Think Comes Out of These Eggs | 39:46 | 212,329 | |
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| 2023-08-24 | Drawing Things Our Fans Explicitly Told Us Not To | 46:48 | 304,770 | |
|
| 2023-08-21 | FOUR Artists Draw Characters Using the SAME Description | 42:27 | 524,069 | |
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| 2023-08-17 | Making NEW Teenage Mutants out of Random Generators | 50:57 | 271,976 | |
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| 2023-08-15 | Making Art out of our Worst Spam Emails | 34:33 | 198,044 | |
|
| 2023-08-10 | Redesigning Invader Zim in Different Styles | 26:44 | 172,464 | |
|
| 2023-08-08 | Drawing Victorian Slang Without Knowing What it Means | 43:09 | 250,517 | |
|
| 2023-08-03 | Hero and Villain Drawing CHALLENGE | 30:39 | 230,406 | |
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| 2023-08-01 | Turning My Childhood Favorite Media Into Modern Art | 30:06 | 230,756 | |
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| 2023-07-27 | Turning Fonts Into Characters | 34:17 | 326,341 | |
|
| 2023-07-25 | Drawing Barbies Based Only on Their Names | 39:23 | 352,661 | |
|
| 2023-07-06 | Drawfee is Going On VACATION | 59:57 | 311,679 | |
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| 2023-07-04 | Artists Redraw Their Old Portraits (Once Again) | 36:19 | 558,080 | |
|
| 2023-07-01 | ...did anyone remember to make the anniversary merch ad? | 1:37 | 191,083 | |
|
| 2023-06-29 | Drawing Pokémon That We Generated Using Our OWN NAMES | 42:23 | 313,385 | |
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| 2023-06-27 | Drawing Middle Evolutions for Pokémon That Never Had Them | 38:19 | 362,013 | |
|
| 2023-06-22 | We Made Him Draw Whatever We Told Him... | 21:33 | 246,420 | |
|
| 2023-06-20 | Drawing Digimon Based Only on Their Original Sprites | 34:04 | 211,644 | |
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| 2023-06-15 | I Made Myself Draw Backgrounds Every Day for a Week | 25:37 | 292,161 | |
|
| 2023-06-13 | We Literally Just Made Karina Draw Hot Monsters for 40 Minutes | 44:48 | 410,503 | |
|
| 2023-06-08 | Drawing Words With No English Translation | 47:24 | 255,660 | |
|
| 2023-06-06 | Drawing Games Based on Randomly Generated Titles | 46:19 | 315,564 | |
|
| 2023-06-01 | Legend of Zelda + JoJo's Bizarre Adventure: Style Mash-Up Challenge | 21:34 | 271,704 | | The Legend of Zelda
|
| 2023-05-30 | Redrawing Famous Surrealist Art Using Only a Description | 51:29 | 334,605 | |
|
| 2023-05-25 | Drawing Sonic Characters Based Only on their Vibes | 58:57 | 342,097 | |
|
| 2023-05-23 | Making Drawings out of Randomly Generated Sentences | 41:44 | 261,019 | |
|
| 2023-05-18 | Video Game Genre Swap Drawing Challenge | 19:06 | 180,106 | | The Legend of Zelda: Breath of the Wild
|
| 2023-05-16 | Drawing Anime Characters Based Only on the Eyes | 42:06 | 306,739 | |
|
| 2023-05-11 | Anime Genre Swap DRAWING CHALLENGE | 18:13 | 208,580 | |
|
| 2023-05-09 | Randomly Generated Caution Signs Drawing Challenge | 46:46 | 318,606 | |
|
| 2023-05-04 | 90s Cartoon Redesign Drawing Challenge | 18:55 | 215,852 | |
|
| 2023-05-02 | Designing Mascots for Towns with the Funniest Names | 45:17 | 340,548 | |
|
| 2023-04-27 | Making Characters out of Random FUTURE NAMES | 39:29 | 232,778 | |
|
| 2023-04-25 | Turning Monster Hunter Armors BACK Into Monsters | 53:10 | 309,310 | | World of WarCraft
|
| 2023-04-20 | We Only Had 30 Seconds to Draw These Popular Characters | 25:15 | 259,222 | |
|
| 2023-04-18 | Pro Artists Redraw Their Old OCs | 43:21 | 456,592 | |
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