10. They Might Be Giants - "Birdhouse In Your Soul" (1990)
Certainly the most lyrically baffling of all the videos on this list ("Blue canary in the alley by the light switch, who watches over you?) this was a fitting entry point for a generation into the world of alternative music: friendly and bright enough to invite you in but with enough of a witty and baffling edge to keep you interested. TMBG have become a long-running institution, and have released enough children's records by now to warp the brains of multiple generations. Good going, gentlemen. http://www.youtube.com/watch?v=NAbZzdalZh4
9. Backstreet Boys - "I Want It That Way" (1999)
Kings of the late 90's boy band boom, this flashy, brightly lit clip shows the Boys at the heights of their powers, walking slowly in formation, exiting jets and staring at adoring, rabid fans. Harmonic and sweet yet instantly disposable as was the fashion at the time, this pop confection is still a massive hit at weddings and proms. Your mom and your sister probably like it. If you're being completely honest, you do too. http://www.youtube.com/watch?v=4fndeDfaWCg