Sonic Youth's video for the song "100%" has always been a favorite of mine. There is something about music and skateboarding that go together seamlessly. The song and video are both pretty chill and make me reminisce about my younger years of hanging out, skateboarding and just being a kid.
Unsane's video for the song "Scrape" is another cool skateboard-related music video. To me, this is cool for the opposite reasons that the Sonic Youth video for "100%" is cool. This video is dirty, aggressive and jarring. All the skate footage in the video is of people slamming hard. At the very end of the video, someone sticks a solid grind down a rail. I always had a love/hate relationship with the slam portions of skate videos. I would love watching people completely eat shit, but afterwords I really didn't want to go out skating.
The Toadies' video for the song "Possum Kingdom" is the only thing I have ever seen or heard from this band. The song itself is a solid example of '90s grunge/alternative music. The video is a little disturbing with scenes of a person dragging a body and digging a grave at the beginning. It all culminates with the killer actually creating an ice sculpture which has you rethinking the whole video. I wish people still did the pogo at shows like in this video.
The Guns N' Roses' video for the song "You Could Be Mine" is unintentionally funny while still being ass-kickingly awesome. How can anything with The Terminator in it from the '90s not be awesome? The premise of the video is that a Terminator was sent back in time to kill Sarah Conner and failed, but now it has a new target: Guns N' Roses. The end of the video is priceless with Arnold's assessment of his target.