This very impressive video for Weval's Someday, done by Páraic Mc Gloughlin (warning, possible seizure-inducing imagery), got me thinking. It's a great track in and of itself, but the sheer quality of the work on the video just wowed me. It came from a totally different angle than I envisioned in my mind when just listening to the song... yet when I read his take on it, it made perfect sense.
Otherwise, the White Stripes' I Fell In Love With A Girl and Alt-J's NSFW-ish vids for Every Other Freckle also come to mind, both the male and female versions. Also, This Is America by Childish Gambino. I'm struggling to think of other videos that really struck me, but that might just be my poor memory. Any suggestions?
Edit: Forgot some classics!
The Spike Jonze-directed Drop from The Pharcyde, with a nice peek behind the curtain here. A (Canadian?) rapper named Shad did a really cool tribute to that video with his own Rose Garden that put a nice spin on it.
Jamiroquai's Virtual Insanity (and another peek behind the curtain here)
Hype Williams + Busta Rhymes was always a gold combination, and their best collab was probably Gimme Some More
A-ha - Take On Me
Another NSFW one, D'Angelo's Untitled.
I also just remembered coming across Sour's Hibi no Neiro a few years ago and thinking it was such a really cool concept to essentially crowdsource a music video... reminds me of what Youtube used to be like.