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Just to clarify, what I did for these was look through all the AMVs that I'd locally downloaded and given 5 stars on animemusicvideos.org. (This isn't all of them.) And there's another related post here.
"Lost in an Anime Dream" by JudgeHolden (Read Or Die (TV), Lost in Translation, Madonna)
I remember really clearly, the first time I watched this vid, thinking "This isn't an AMV!" But with the benefit of years more experience I realized that it is in fact an AMV--for all that 2/3 of the source footage is live action, all of it is used in a very AMV-aesthetic way. And the technical skill involved almost goes without saying. (Read Or Die: The TV is a television spinoff of the OVA Read Or Die, which is generally agreed to be a bit better than the TV but which features only some of the same characters. What you need to know is that the world's libraries have special operatives who can manipulate paper into whatever they desire. They are called the Paper Sisters, or just the Paper.)
"Waking Hour" by Koopiskeva (Kumo no mukou, yakusoku no basho | The Place Promised in Our Early Days)
Koopiskeva is one of the really famous editors of AMVs; one of their vids remains at the top of amv.org's all-time star scale. This vid is set to an anime by Shinkai Makoto, who is probably the progenitor of and definitely the foremost practitioner of the recent "sekai-kei" anime…school? style? For our purposes the important point is that all Shinkai's anime feature characters who, despite being separated by great distances, remain connected. The other important point is that Shinkai made his first anime, Voices of a Distant Star, by himself on his laptop. AMV creators have access to all those same technologies when making their vids, which is one of the things I think of when I talk about the convergence between transformed and original content in AMVs.
"Clear Skies" by Mamo! (Kaleido Star)
I have a weakness for Kaleido Star (AMVs), which is why there are two of them in this list. The anime is about a girl who joins the circus. And then later it more or less becomes a magical girl anime. But, seriously! Just look at those girls! Aren't they awesome? They're awesome! (Also, those sparkles in the AMV? Not digitally added.)
"Nightmare" by MousePotato (Neon Genesis Evangelion)
There's no way for me to explain EVA if you don't know about EVA. Read the Wikipedia article, I guess. But, anyway, it goes without saying that there are a million EVA vids, just as there are a million EVA essays, papers, and fan commentaries, and out of all of them this is the one I like best.
"Running Man" by Nostromo_vx (multi)
Nostromo_vx is another famous editor, and this is a monster of a vid, literally; if you're running an older computer your only hope is to use VLC, which automatically drops frames to keep the sync going. (You could also ddl the 30fps version.) Um, but yeah, it's pretty amazing. Particularly the partial Haruhi dance in the middle, which I can guarantee you does not happen in the source footage.
"Scarlet Touch and Roses Rain" by WUNETTI Productions (Revolutionary Girl Utena, the movie: Adolescence of Utena)
Oh, this AMV. Oh, this movie. If you haven't seen the movie, watch it. I guarantee that you will like it. It is a headtrip, but it is also gorgeous, radical and amazing. And the AMV does what it says on the tin--that is, it's art.
"The Wizard of Ozaka" by suberunker and EricaOhayou (multi)
I like this AMV because it unifies some rather diverse things--anime, The Wizard of Oz, Chicken Run--in a really clever way, and I don't think it takes much familiarity with any of them to get a real kick out of the AMV.
"Sail On" by Inertia (One Piece)
This is a really popular AMV by a well-known editor, and I think it's a great introduction to the show, despite the fact that the footage is almost entirely from the movies.
"Noise" by Megamom (multi)
This is another just technically amazing AMV, and it doesn't require much familiarity with the source footage to appreciate. So go watch it.
"Redona" by oro$hi (multi)
Visually amazing, blah blah blah, go watch.
"Ian Fleming's Property of a Lady" by qwaqa (multi)
It seems like there are a lot of AMVs that draw on James Bond, probably because there are a lot of anime that have women with guns, and this one is particularly great because so much of it is original--the credits to a Bond movie cast with anime heroines, in which the anime girls are the Bond credit girls. It's pretty awesome.
"罪人の火傷 | Tsumibito no kashou" by Tyler_yi (Fullmetal Alchemist)
There are newer FMA AMVs, but I daresay there aren't any that are better.
"Spirit of the Stage" by JCD and Messi (Kaleido Star)
This is the other Kaleido Star AMV. They do slightly different things in a way that I think gets at the nature of AMVs. Also it's just a really well edited vid. I love this anime. And again, the sparkles are not digitally added.
"Skittles" by Koopiskeva (The Melancholy of Haruhi Suzumiya)
This is the AMV that sits on top of amv.org's all-time star scale, and seriously, you have to see it. This anime was paradigm-changing for the industry, in a lot of ways, and its effect on fandom globally is incalculable--search for "Haruhi dance Akihabara" on YouTube and you'll see what I mean. It's Haruhi's world; we all just live in it. Also the vid is doubly hilarious if you've seen the anime, but you'll be wowed regardless.
"Magic Pad" by Nostromo_vx (multi)
This is another AMV that almost transcends anime; it's not really about the source footage so much as it uses and transforms the source footage into something that is almost entirely its own thing. In any case, that thing is visually amazing.
"Hold me now" by alkampfer81 (Princess Tutu)
The anime is a ballet magical girl anime in which a duckling becomes a girl to save the prince. Once you watch the AMV you will be consumed with the desire to see the anime, because the AMV is beautiful and amazing and the anime lives up to it. So go watch them both.
"Lost in an Anime Dream" by JudgeHolden (Read Or Die (TV), Lost in Translation, Madonna)
I remember really clearly, the first time I watched this vid, thinking "This isn't an AMV!" But with the benefit of years more experience I realized that it is in fact an AMV--for all that 2/3 of the source footage is live action, all of it is used in a very AMV-aesthetic way. And the technical skill involved almost goes without saying. (Read Or Die: The TV is a television spinoff of the OVA Read Or Die, which is generally agreed to be a bit better than the TV but which features only some of the same characters. What you need to know is that the world's libraries have special operatives who can manipulate paper into whatever they desire. They are called the Paper Sisters, or just the Paper.)
"Waking Hour" by Koopiskeva (Kumo no mukou, yakusoku no basho | The Place Promised in Our Early Days)
Koopiskeva is one of the really famous editors of AMVs; one of their vids remains at the top of amv.org's all-time star scale. This vid is set to an anime by Shinkai Makoto, who is probably the progenitor of and definitely the foremost practitioner of the recent "sekai-kei" anime…school? style? For our purposes the important point is that all Shinkai's anime feature characters who, despite being separated by great distances, remain connected. The other important point is that Shinkai made his first anime, Voices of a Distant Star, by himself on his laptop. AMV creators have access to all those same technologies when making their vids, which is one of the things I think of when I talk about the convergence between transformed and original content in AMVs.
"Clear Skies" by Mamo! (Kaleido Star)
I have a weakness for Kaleido Star (AMVs), which is why there are two of them in this list. The anime is about a girl who joins the circus. And then later it more or less becomes a magical girl anime. But, seriously! Just look at those girls! Aren't they awesome? They're awesome! (Also, those sparkles in the AMV? Not digitally added.)
"Nightmare" by MousePotato (Neon Genesis Evangelion)
There's no way for me to explain EVA if you don't know about EVA. Read the Wikipedia article, I guess. But, anyway, it goes without saying that there are a million EVA vids, just as there are a million EVA essays, papers, and fan commentaries, and out of all of them this is the one I like best.
"Running Man" by Nostromo_vx (multi)
Nostromo_vx is another famous editor, and this is a monster of a vid, literally; if you're running an older computer your only hope is to use VLC, which automatically drops frames to keep the sync going. (You could also ddl the 30fps version.) Um, but yeah, it's pretty amazing. Particularly the partial Haruhi dance in the middle, which I can guarantee you does not happen in the source footage.
"Scarlet Touch and Roses Rain" by WUNETTI Productions (Revolutionary Girl Utena, the movie: Adolescence of Utena)
Oh, this AMV. Oh, this movie. If you haven't seen the movie, watch it. I guarantee that you will like it. It is a headtrip, but it is also gorgeous, radical and amazing. And the AMV does what it says on the tin--that is, it's art.
"The Wizard of Ozaka" by suberunker and EricaOhayou (multi)
I like this AMV because it unifies some rather diverse things--anime, The Wizard of Oz, Chicken Run--in a really clever way, and I don't think it takes much familiarity with any of them to get a real kick out of the AMV.
"Sail On" by Inertia (One Piece)
This is a really popular AMV by a well-known editor, and I think it's a great introduction to the show, despite the fact that the footage is almost entirely from the movies.
"Noise" by Megamom (multi)
This is another just technically amazing AMV, and it doesn't require much familiarity with the source footage to appreciate. So go watch it.
"Redona" by oro$hi (multi)
Visually amazing, blah blah blah, go watch.
"Ian Fleming's Property of a Lady" by qwaqa (multi)
It seems like there are a lot of AMVs that draw on James Bond, probably because there are a lot of anime that have women with guns, and this one is particularly great because so much of it is original--the credits to a Bond movie cast with anime heroines, in which the anime girls are the Bond credit girls. It's pretty awesome.
"罪人の火傷 | Tsumibito no kashou" by Tyler_yi (Fullmetal Alchemist)
There are newer FMA AMVs, but I daresay there aren't any that are better.
"Spirit of the Stage" by JCD and Messi (Kaleido Star)
This is the other Kaleido Star AMV. They do slightly different things in a way that I think gets at the nature of AMVs. Also it's just a really well edited vid. I love this anime. And again, the sparkles are not digitally added.
"Skittles" by Koopiskeva (The Melancholy of Haruhi Suzumiya)
This is the AMV that sits on top of amv.org's all-time star scale, and seriously, you have to see it. This anime was paradigm-changing for the industry, in a lot of ways, and its effect on fandom globally is incalculable--search for "Haruhi dance Akihabara" on YouTube and you'll see what I mean. It's Haruhi's world; we all just live in it. Also the vid is doubly hilarious if you've seen the anime, but you'll be wowed regardless.
"Magic Pad" by Nostromo_vx (multi)
This is another AMV that almost transcends anime; it's not really about the source footage so much as it uses and transforms the source footage into something that is almost entirely its own thing. In any case, that thing is visually amazing.
"Hold me now" by alkampfer81 (Princess Tutu)
The anime is a ballet magical girl anime in which a duckling becomes a girl to save the prince. Once you watch the AMV you will be consumed with the desire to see the anime, because the AMV is beautiful and amazing and the anime lives up to it. So go watch them both.