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Horseshoe Finale (2015)
If you're reading this, you're probably a fan.
Horseshoe Finale's hard to explain if you aren't--not to say that I have a suitable enough understanding to explain it. In my cretinous interpretation, HF is the culmination of Drowning in Footwear and Drowning in Horseshoes: two YouTube serials (that's the only way I can explain them) about meta, genre, nostalgia, critique, creative experimentation, comedy, artistry, pro wrestling, ponies, and more. It's finishing off the character arc of the Horseshoe Man in a celebration and parody of himself, art, and everything else he's been talking about.
Jessie's videos are so interesting because they have this genuine artistic feel. YouTube videos are usually done in such a way where you get 100% of the creator's intent immediately, but with Jessie, you feel a need to look underneath the surface level to get what's going on. I remember when I found his channel when I was fifteen-ish, it was the first time I felt intellectually challenged by a YouTube video. It sounds incredibly silly, but it's true. There's this alluring mystery that you find in art you're too stupid to figure out.
Even if I'm completely wrong about all of Jessie's artistic intentions, it's still quite the mesmerizing experience.
It's pretty funny. I recommend it.