@jackamomo: There's a sitcom called "You're the Worst" where basically two relatively misanthropic people (a British guy author and an American girl talent agent) get together based on their mutual dislike for the rest of humanity. At one point in a later season, they get sent baby photos from a mutual friend who just had a baby. Looking at the photos on their phones, they go back and forth making comments about how incredibly ugly the baby is. One of Jimmy's comments was "Oh my god! It looks like it should be screaming at an old woman in an Aphex Twin video!" which I laughed my ass off at. BEST JOKE EVER, although I had to explain it to my wife and then show her the video for "Come to Daddy".
As for me, I'm ashamed of our community that nobody has already thrown up the following entries:
Take on Me literally one numerous awards for Music Videos.
Actually there are a lot of Peter Gabriel/Genesis videos that were really impressive and imaginative.
Wait, Christopher Walken got his start in song and dance instead of just by being the creepiest mofo on screen??!?!?
And of course...
But you want to go more contemporary, I'd go with Hideaway which is done in a single take on the streets of Manhattan:
Centipede by Knife Party for creating an awesome "Naked Lunch"esque storyline:
Revival by Beats Antique for creative and unique imagery:
But honestly there are so many. Pretty much everything by Tool could be on this list. Primus as well. I grew up in the era of music videos.
-Byshop
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