Matthew Sweet – Girlfriend (1991)
I actually think this video has dated pretty well, especially when you consider how difficult it is to blend animated and live-action footage like this (and on quite the modest budget compared to the next video), and the huge potential for it all to go terribly wrong. The footage here comes from the 1982 film Space Adventure Cobra, which I haven’t seen so I can’t comment on what connection the it may have (if any at all) with the lyrics to the song. I’ll admit that the first half of this video kind of meanders but the second half is pretty good by early 90s alt. rock video / early AMV-standards. If this video wasn’t enough for you, check out the one for his next single, “I’ve Been Waiting,” which features lots of footage from the iconic 80s title Urusei Yatsura.

Michael Jackson – Scream (1995)
Apparently this video cost seven million dollars to make, a record that I doubt will be broken any time soon in our age of cheap viral video hits. Anime clips are used sparingly — blink and you’ll miss them — and seem to be borrowed from Akira and a handful of other titles. Don’t forget, this video was a big deal when it came out! I didn’t have cable when this was released and I know it was aired on network television, so lots of people saw this.

Chage and Aska – On Your Mark (1995)
Hayao Miyazaki directed this original music video, which is the earliest example I can find of a completely original anime music video. I find it hard to believe that this was the first of its kind, but whether or not it was, it’s certainly one of the most ambitious music videos of any kind that I’ve ever seen. The song itself seems completely incidental to the dramatic video, which nearly buries it in its own sound effects (for the better, IMO). A must-see for any Miyazaki fan. Kind of a pity that Youtube and/or Ghibli seem intent on taking it down every time someone uploads it for all to view.

Ghostface Killah – Daytona 500 (1996)
The history behind this video doesn’t seem to be well-documented, but the ID tags at the beginning of this copy of the video seem to suggest that it was, in fact, recorded from a television broadcast. Wu Tang’s fondness for the far east is well-known, but I always thought it was chiefly rooted in Chinese culture and film. Still, I don’t think it’s a stretch to assume that the same guys who borrowed much of their mythology from Hong Kong kung-fu movies could also have a soft spot for classic Japanese anime as well. Did the creators and owners of Speed Racer sign off on this music video? Or did they notice but turn a blind eye to it? Life in the 90s being so less connected than it is now, is it possible that no one at Tatsunoko Productions even noticed this when it was released? Wikipedia cites this as “one of the earliest anime music videos ever made,” which is kind of a ridiculous and unfounded statement, but anything of this nature appearing in the 1990s is worth a second look today.

Daft Punk – One More Time (2001)
Essentially the opening to the film Interstella 5555, which was released in 2003, but I know I saw this video at least a year or two before that. I found it hard enough to wrap my mind around this song when I first heard it, but the video… I think I assumed that they were both made in the spirit of parody (of 80s pop and AMVs in general, respectively). I really wish I could go back and slap some sense into myself back then, as I wholeheartedly adore both today. Interstella 5555 just might be my favorite film of the decade; hopefully this video will help keep it fresh in fans’ minds for years to come.

Linkin Park – Breaking the Habit (2004)
The most mistakenly dismissed band of all time? I know, I know. “Lol, Linkin Park!” etc. But this is a great song. The music video, developed by Studio 4°C, continues in the style they contributed to Quentin Tarantino’s Kill Bill. It’s as angst-ridden and moody as you’d expect, but it’s also really interesting and well done. Not “anime” in the classic style that we’d expect, but an eye-opening and really cool work nonetheless.

Radiohead – 15 Step (2008)
Maybe not a “real” AMV, but one of the winners of Radiohead’s music video contest for their album In Rainbows. “15 Step” was never a proper single and never received its own official video, so it’s probably safe to say that this one, hand-picked by the band themselves out of more than a thousand entries, qualifies as an official video in its own right. I’ve no idea what its creators are doing now but I hope they move on to bigger success in the future, though I guess the prospects for aspiring animators in Japan aren’t exactly the most encouraging right now. I’m not even sure if I really like this video or not, but I think these guys have potential.

Queen – Bohemian Rhapsody (2009)
I don’t know what prompted Leiji Matsumoto to create this video, what connections may exist between the song’s lyrics and the video’s story, or if it reaches the heights of his work with Daft Punk, but it’s still a pleasure to watch, and reminds me how badly I need to watch some of his classic works (I’ve been meaning to for the longest time, I swear).