The High Maintenance Guy Curated You the Ultimate YouTube Playlist

Ben Sinclair. Photo: Evan Agostini/Invision/AP/Shutterstock

There’s a low-stakes intimacy to showing somebody your favorite YouTube video. You’re saying you know someone well enough to believe a video that really does it for you will also really do it for them. You’re exposing yourself. If it goes well, you get to watch somebody experience the fleeting but hearty joy that only a particularly good YouTube video can offer. If you fail, well, then you’re the cruel weirdo who thinks watching a little girl fall off her pony and get nailed by an ostrich is funny.

Ben Sinclair decided to have that experience over and over this summer, emailing his friends asking for YouTube video recommendations as research for a forthcoming episode of his HBO show, High Maintenance. The result is a crowdsourced Google spreadsheet of nearly 200 videos. There’s your classics, like “Christian the Lion” and “Apparently Kid,” and that one where the anchor mistakenly uses the word “gay” instead of “blind.” But the list also includes deep cuts, with plenty of weird, funny, and sweet stuff you maybe haven’t seen before. Like a live Lena Horne performance, Liza Minelli on the Home Shopping Network, and Japanese commercials for soy beans.

“I was trying to use what YouTube somebody recommends as like some sort of way to show what they’re into … as like some sort of personality litmus test,” Sinclair told Vulture. Sinclair left Twitter two years ago and Instagram in April — 4/20, to be specific and very on-brand — and says he got off Facebook “whenever Osama bin Laden was assassinated.” So he went old, or, uh, older-school. “I just wanted to crowdsource what my friends were into, and then I just did it the way that you would’ve done it in 2006 or whatever, which is I just wrote emails,” he explained. “What is nice about this project is every time someone submitted something, then I had an email thread with them, so not only would we talk about this video, but I would just get to catch up with somebody I haven’t seen in awhile.”

Sinclair also talked about the snap-judging that happens when you ask everybody you know, effectively, to reveal their true sense of humor. “There’s one person on there. I gotta blow up his spot, because this is funny, but Josh Siegel, who runs film at MoMA, the video he put up was ‘Toddler Getting Kicked by Breakdancer.’ Of all of the things he could’ve put up, he put up ‘Toddler Getting Kicked by Breakdancer,’ and he has his own kids too, and that’s just hilarious, man. Like, that right there is just like so human.” Another friend added “80 Year Old Sky Dive Goes Wrong,” which Sinclair said is a “pretty fucking upsetting” clip, while somebody else contributed “Reporter Makes Kid Cry on First Day of School,” which still involves laughing at a crying pre-kindergartner but is a little less, well, fucking upsetting. (This video of a woman giving instructions on how to massage a cat while staring straight into the camera seemingly without blinking … possibly the most upsetting.)

The project was also about grappling with how pervasive and often necessary technology has become in our culture — YouTube videos are fun, but they are also brought to us on a problematic platform owned by a fraught tech giant — while also trying to get more offline. “I’m not an extremely political person. I try to rise above that and get on the, you know, spiritual plane. We’re all just space dust or whatever, some bullshit like that, but I do feel like, fuck Zuckerberg, man. This shit sucks,” Sinclair said. “It’s a total monopoly. It’s gotten to the point where it’s, like, affected our government. It affected how we think about ourselves, and our psychology, and all of that shit. You know when people used to hand around dubbed VHS tapes? There’s something that felt so cool about that. It felt so much more exclusive, because of the relationships you had and the people you knew. It’s almost impossible to discover anything anymore. I’m a 1984-born millennial. We always want to discover everything first, and it’s fun to do that through email and not through fuckin’ feeds.”

“Ultimately, I would have loved to throw an actual party, and just have this be the premise of it,” Sinclair said. “Submit your videos before, because you know when you get to the party and you’re selecting YouTube things right then, you know there’s that moment where you put on a video and then you’re watching and no one’s laughing and you’re fucking embarrassed because it was the wrong video or it’s not as good as you remembered or it’s just falling flat. I think it would be fun to have this as like, a pre-made party YouTube playlist.”

You can throw your own YouTube party using Sinclair’s spreadsheet here —contributors’ names have been removed to protect the innocent — or watch the individual videos from the list below.

Lena Horne on Speed

Stephen A. Smith: Stay Off the Weed

Fart House

Let’s Paint, Exercise, & Blend Drinks

The Wolves of Wall Street

Coyote in Chicago

Farewell Haka for Mr. John Addams

Gaga Says There’s One Hundred People in the Room

Breakdancer Kicks a Toddler

Hermeto Pascoal

Pollo Crocodillo

’Apparently’ Kid

Riverdance on Ice - Figure Skating Championships 2014

Turkish Man Yelling “Meow” at an Egg

He Doesn’t Want to Host the Show Anymore (Steve Harvey)

Forget About Everything



Cher Lloyd by Cher Lloyd (Shit Cover)

Paul Lynde & Hollywood Squares: BEST-1-LINERS Part 1

Ultimate Dog Tease

Old School Rap - Three the Hardway and White Flash 1988

2:30am at a 7-11 near Disney World - 1987

Grape Stomping Lady Falls

Stevie Nicks - Wild Heart - Live Demo - 1981

Honey Badger

Chinese Ping Pong Match

History of the Entire World, I Guess

Pinky the Cat

Jordan Peterson | ContraPoints

Transformer Owl

Funny Trigon Commercial: He Kicked Him in the Penis

He’s Gonna Kick MY Ass?

God Is Doing a New Thing

The Radical

Pot Brothers

Little Girl Cuts Her Hair in Bathroom

Kim Cattrall Scatting

Samuel L. Jackson in Grease

In My Feelings Challenge With a Cow

Shrek Wrecks Kids Party

Friends of the Garden

That Dumb Song Fireflies with Dog and Cat Instead of Person

The Bully & The Beast: Wax Catches Poop

80-Year-Old Woman Sky Dive Goes Wrong

Reporter Makes Kid Cry on First Day of School (Back to School)

Jim Backus & Friends : Delicious

I’m Afraid to Talk to Men

Angry Ram

Possum Massage

Indian Thriller

Safety PSA Spot

Eagle Throws Goat

Crazy Frog Brothers


Drunk Man Sings ‘Bohemian Rhapsody’ From the Back of a Police Car [Actual Police Video]

The Complete Saga of Harmony Korine on Letterman (and Why He Got Banned for Life)

We Are Here: The Pale Blue Dot

Wallet Thief Changes His Mind When He Sees a Surveillance Camera

The Original Technoviking Video

Georgie Pants

Adriano Celentano - Prisencolinensinainciusol

8th Grade Homecoming Skit - Second Place - 2014

Dennis Parker - Like an Eagle (1979)

Star Wars Trumpet

Meghan Markle’s Face Doesn’t Move

Performance of ‘I Will Always Love You’ (Whitney Houston) Creepy Lip Sync Contestant (Philippines)

Turtle Sex With a Shoe

Jesus Chroist Pop and Lock

In Ictu Oculi, 2009 (Vultures Destroying Dinner Table)

Man Sees Color for the First Time

Zoobilee Zoo Alternative Intro

Scarlet Takes a Tumble

Man Showering While Smoking

Snowball the Dancing Cockatoo x Backstreet Boys

Beyoncé Makes Fan Sing

Serene Branson Has a Stroke on Air?

AWOLNATION ‘Sail’ and Funny Cats

9GAG Crying While Dancing Little Sheep Baby

More Sand

Ms. Peachez in the Tub

Moped Dance

Chicago Botanic Video

Sotho Sounds

Cher - West Side Story | From ‘Cher … Special’ (1978)

Iron Mic: Eli Porter vs. Envy

The Elephant’s Garden

The World’s Most Awkward Interview - Mr. Wacky

Catch the Ice Dude

Countdown: Iggy Pop Interview and ‘I’m bored’ Studio

Man Falling Out of Kayak

Nicolas Cage Loses His Shit

Jim Bakkers Buckets

Mad Bitches Link Up Alert

Nicolas Cage Knows How to Make an Entrance

I Smell Like Beef

Lizard Jumps on Newscaster

Model Falling

Madeline Kahn Monologue

Funny Pine Sol Commercial Surprises People

Melanie Raccoon Sweeping the Floor


Musicless Musicvideo / DAVID BOWIE & MICK JAGGER - Dancing in the Street

Eartha Kitt on Love and Compromise

Rhiannon Fleetwood Mac Live 1976

World’s Best Yoyo Tricks 2017

Allen Ginsberg Live at the Pyramid Club 1989

Arab Drifting

Sick Drone Footage of Drifting Race Cars

Dangerfield on Carson ’82

Disney on Ice in One Minute

Spelling Bee Faint

He’s Gay He’s Blind


Santana Shreds

The Rainbow Sponge

Cat Massage

Liza on HSN

Squirrel Hides Nuts in a Bernese Mountain Dog’s Fur

Don Cherry’s Piano Desk


Amazing Japanese Soy Bean Commercials

Little Kid Meets Lobsters

Cooper Loves Ice Cream

Flutterby Fairy

Old Lady Road Rage Revenge

Lindy Hop Hellzapoppin

Gorgeous Tiny Chicken Machine Show ep 1, 2, & 3

Indian song Subtitled by Buffalax

Can’t Tell Me Nothing - Zach Galifianakis

Big Boi’s Favorite Verse: Kate Bush’s ‘Running Up That Hill’ | VERSES

Whitney Houston - Star Spangled Banner

’Seagulls Stop It Now’ Bad Lip Reading

Tierra Whack

Rubber Bandits - Horse Outside

Prefab Sprout: Earth the Story So Far

Billy Corgan Rides a Roller Coaster

Radio 4’s Charlotte Green Cracks Up on Air

James Brown Drunk (Full Version)

Do It Debbie’s Way: Debbie Reynolds Workout Tape


Pillow Talk

Hula Chair

Middle Finger Fight

Christian the Lion

’Thriller’ Prison Dance

Highlights From Wildwood, NJ

Floating Dog

Drunk Orson Wine Commercial

Hanna Barbera Anti Drug PSA

It’s a Whale, Jay

Woman Runs and Jumps Like a Horse

Small, Angry Man Yells at Trumpet Player in New York City

Chris Crocker - The B**** Bell!

Little Superstar

Goat Attacks News Lady

Yule Log With Family Argument



Master Chef

The Martha Stewart Show Blooper Reel ⎢Martha Stewart

Couple Watches Their Cat

A Crazy Looking Cat at His Mom’s House!

Appalachian State University Is HOT HOT HOT

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