Another difficult question. Probably from Year 2 through year Six, I watched MTV a LOT. Watched the video countdown almost every week, then not so much. I should note that, for the body of video work, I’d probably pick Billy Joel.
There are probably only three post-1995 videos I both saw and liked enough to even consider. Hey Ya by Outkast (and here’s a longer, though not better version) and I Am A Man of Constant Sorrow by the Foggy Mountain Boys are two of them.
Plenty of good picks in this list of best videos and in this one, although many of the actual videos have been disabled. Two on those lists that I was quite fond of were Once In a Lifetime by the Talking Heads and Sledgehammer by Peter Gabriel. I was an irrationally big fan of Weird Al Yankovic’s Smells Like Nirvana.
If I had to pick one video, it would probably be Hurt by John R. Cash, which I watched over and over. But let’s face it, it’s a bit of a downer. So I don’t know that it’s my favorite, but one I watched a great deal in the day: Would I Lie to You by Eurythmics; I’m especially fond of the ferocity of Annie Lennox and the brass.