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| | time | views | |
| "My Friends" - Drew Monson (Official Music Video) | 5:26 | 233,208 | |
| I Got a New Hat (not clickbait) | 19:19 | 179,096 | |
| Why people are mad at me | 28:22 | 288,576 | |
| 99 Cent Store Haul! (2019) | 13:36 | 245,644 | |
| Making Fun of My Childhood Photos | 11:17 | 208,801 | |
| I Followed a Morning Routine | 16:50 | 307,306 | |
| I Hit on a YouTuber | 16:29 | 269,207 | |
| Why I Hate Men | 11:46 | 386,142 | |
| Dollar Store Haul! | 10:20 | 410,583 | |
| How I Gained 50 Pounds | 10:42 | 482,199 | |
| Why I Deleted My Tinder | 12:40 | 347,912 | |
| Drew and Drew's Grandma Podcast Episode 2 VIDEO | 46:23 | 168,780 | |
| How to Live with Depression | 18:57 | 381,561 | |
| Explaining my leaked video | 14:54 | 767,733 | |
| Making Fun of My Childhood Art | 19:31 | 556,308 | |
| I Accidentally Dated a Fan | 10:30 | 757,174 | |
| Recreating My Old Videos | 9:34 | 608,925 | |
| Goodbye Drew Monson? | 10:38 | 2,378,878 | |
| BIG ANNOUNCEMENT | 2:32 | 589,297 | |
| I'm back | 9:19 | 719,127 | |
| Reacting to Compilation Videos of ME | 7:24 | 3,255,852 | |
| MY NEW APARTMENT TOUR | 8:37 | 868,137 | |
| MY COMEBACK - MUSIC VIDEO by Drew Monson | 4:31 | 3,175,631 | |
| "FANTASIES" TRAILER | 1:40 | 326,339 | |
| GETTING MY EYEBROWS WAXED | 9:14 | 809,411 | |
| My Grandma Reads My Hate Comments | 8:00 | 937,829 | |
| Why I Left YouTube | 10:50 | 1,685,000 | |
| EATING PIZZA AND TALKING ABOUT LEAVING YOUTUBE | 28:45 | 1,041,573 | |
| GIANT ICE CREAM SUNDAE (with SHANE DAWSON) | 10:39 | 2,818,943 | |
| GRANDMA PLAYS *POKEMON GO* | 6:58 | 436,891 | |
| TESTING AS SEEN ON TV PRODUCTS #3 | 7:42 | 1,020,446 | |
| WHAT IT'S LIKE TO BE 21 | 9:17 | 559,860 | |
| 99 CENT STORE HAUL #2 | 10:19 | 778,782 | |
| Why I'm So Weird | 8:59 | 577,231 | |
| My Depression | 8:49 | 859,538 | |
| LOSING MY VIRGINITY | STORYTIME | 7:34 | 708,990 | |
| Talking to Shane Dawson | 6:20 | 1,353,215 | |
| YOUTUBER GOSSIP | 9:44 | 524,195 | |
| Talking to Superfruit | 7:31 | 1,606,888 | |
| My Secret | 10:33 | 550,612 | |
| Kissing My Friend | 8:23 | 1,772,523 | |
| My Sex Life | 7:46 | 606,752 | |
| 99 CENT STORE HAUL | 7:29 | 797,991 | |
| WHY BEING SINGLE SUCKS | 8:17 | 472,972 | |
| TESTING *AS SEEN ON TV* PRODUCTS #2 | 6:15 | 1,433,456 | |
| Did I Get Ugly? | 7:19 | 627,940 | |
| THRIFT STORE HAUL | 8:16 | 834,271 | |
| MY PSYCHIC READING with THE PSYCHIC TWINS | 6:80 | 548,504 | |
| TRYING GIRL THINGS - PEDICURES | 6:11 | 536,817 | |
| I CRACKED MY HEAD OPEN | STORYTIME | 5:40 | 869,853 | |
| I Want a Girlfriend | 6:18 | 574,700 | |
| Kissing Joey Graceffa | 6:25 | 1,079,387 | |
| MY YOUTUBE DRAMA | 6:16 | 538,330 | |
| THE CONDOM CHALLENGE with SHANE DAWSON | 4:16 | 2,037,433 | |
| TESTING *AS SEEN ON TV* PRODUCTS | 7:18 | 1,150,860 | |
| REACTING TO MY OLD VIDEOS #2 | 7:35 | 583,019 | |
| DOLLAR STORE HAUL #4 | 7:51 | 839,088 | |
| PIZZA CHALLENGE with COLLEEN BALLINGER | 7:52 | 1,097,779 | |
| I Got A Haircut | 8:70 | 789,136 | |
| CHAPSTICK CHALLENGE with TRISHA PAYTAS | 6:52 | 1,165,772 | |
| HALLOWEEN STORE HAUL | 7:30 | 593,181 | |
| TMI TAG with MY GRANDMA | 5:35 | 384,267 | |
| BACK TO SCHOOL TIPS | 6:45 | 376,577 | |
| Why Am I Crying | 8:41 | 289,721 | |
| THE SODA CHALLENGE with SHANE DAWSON | 12:11 | 1,561,203 | |
| MAN BUN TUTORIAL | 4:20 | 451,031 | |
| DOLLAR STORE HAUL 3 | 10:60 | 1,092,527 | |
| I'm Tired of Lying | 10:32 | 631,715 | |
| WHY GIRLS THINK I'M UGLY | 5:60 | 403,221 | |
| I'm Getting Fatter | 6:36 | 507,570 | |
| DO I HAVE A GIRLFRIEND? | 7:18 | 469,842 | |
| I'm Gonna Be A Dad | 8:10 | 694,188 | |
| Am I Dating Shane | 7:56 | 1,791,183 | |
| OPENING SNAPCHATS FROM FANS #2 | 4:58 | 542,916 | |
| DOLLAR STORE HAUL 2 | 5:18 | 735,727 | |
| HOW TO SURVIVE YOUR TEENS | 6:22 | 368,771 | |
| REACTING TO MY OLD VIDEOS | 4:48 | 664,040 | |
| MY MOM HATES MY VIDEOS | 5:16 | 756,343 | |
| DOLLAR STORE HAUL | 6:32 | 985,544 | |
| EATING BUG CANDY with SHANE DAWSON | 6:13 | 2,202,584 | 1 list |
| PRANK CALLS WITH MY GRANDMA | 4:56 | 236,647 | |
| OPENING SNAPCHATS FROM FANS | 4:50 | 906,928 | |
| AM I A VIRGIN? | 5:44 | 447,840 | |
| REACTING TO OLD PICTURES with SHANE DAWSON | 4:35 | 1,458,465 | 1 list |
| KYLIE JENNER LIP CHALLENGE | 2:50 | 1,286,027 | |
| THE GIRLFRIEND TAG | 3:35 | 325,318 | |
| GETTING RECOGNIZED IN PUBLIC | 5:31 | 405,539 | |
| FAST FOOD HAUL with SHANE DAWSON | 6:15 | 2,034,261 | 1 list |
| Depression and Suicide | 7:54 | 462,205 | |
| WHAT DOES "MYTOECOLD" MEAN? | 5:50 | 477,033 | |
| MAKING STRANGERS UNCOMFORTABLE | 3:60 | 191,127 | |
| I'm Gonna Be Famous | 6:21 | 254,997 | |
| Am I Ugly? | 6:40 | 506,868 | |
| My Tinder Date | 8:13 | 260,083 | |
| YOU THINK I LOOK LIKE A GIRL? | 5:42 | 442,315 | |
| SH*TTY APARTMENT TOUR | 4:40 | 531,837 | |
| Awkward Collab with LUCAS CRUIKSHANK | 5:70 | 553,288 | |
| KISSING SHANE'S GIRLFRIEND | 7:42 | 525,738 | |
| YOUTUBERS THAT ANNOY ME | 4:58 | 784,873 | |
| SKINNY DIPPING | 6:10 | 309,842 | |
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