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.

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