My two guesses: Beauty & The Beast or Pinocchio. The question only applies to classic Disney films, no Pixar. Besides the obvious factor of timing against past releases, these two hold a special place in the Disney canon.

Pinocchio

Walt was said to have described Pinocchio, his second animated feature after Snow White, as the story closest to his heart, and his quest for perfection nearly broke the studio. Pinocchio lost money in it’s initial 1940 release. However it did ultimately succeed, and Pinocchio is widely regarded as Disney’s most technically perfect animated film. Pinocchio was the first Disney film released on DVD, last available in 1999.

Beauty and the Beast

Beauty and the Beast was the film that saved Disney. Little Mermaid in 1989 was the prelude, showing that the studio was once again capable of producing an animated feature that could cross demographics, introduce lasting characters and revel unabashed in it’s own technical mastery. In 1991, Beauty & The Beast proved Ariel wasn’t a fluke.*

Beauty & The Beast was a huge hit, critically acclaimed and in every way earned its place in the Disney pantheon. Though he obviously never saw it, the story was dear to Walt Disney who twice attempted features based on the story. This was last available on DVD in 2002, and demand is still strong. We’re also approaching the time where the prime audience for the movie’s original release, 7-12 year old girls, are reaching the age where many will be starting families.

Currently I’m feeling about 60/40 Beauty and the Beast over Pinocchio. (I reversed that after writing this, will instinct or reason prove out?)

* I almost deleted that sentence.

Update, October 2008: And now we know. Disney’s first classic to be re-released in HD is Sleeping Beauty. Totally unexpected.

John Gruber linked to the news that Lucas is giving in to demand (eg. money) and will finally release the Star Wars trilogy on DVD in their original, unaltered theatrical format. Han shoots first. John writes:

Bastards. I broke down and finally bought the current DVD trilogy collection just a few months ago now I’ve got to pay for it yet again just to get the versions of the films that I really want.

Hold your wallet. The release will be in SD, despite the news that HD DVDs will start appearing in stores this summer. Lucas, who is as brilliant a money-maker as he is a horrible dialog-writer, will rake in tons of money selling an obsolete DVD. All the Star Wars films will be available again in HiDef soon enough. And too many people will buy them all for the third, fourth or fifth time.

Lucas isn’t alone. All the studios are flooding the DVD market right now to sell as much as possible before the switch to Blu-Ray or HD-DVD.

Supposedly the porn industry likes likes Blu-Ray best, but you’d have to be delusional to think physical pornography sales are anywhere near as strong as they were before the Internet. Still, porn is generally credited with choosing VHS over BetaMax, at least this time they seem to be going with the better format.

Personally, I think HD-DVD may win this time. Not because it’s better, but because “Blu-Ray” is a dumb name. Ask any non-technical consumer what they want for their new HD TV, HD-DVDs or Blu-Ray disks. Sure a certain percentage of people will have Blu-Ray explained to them, “see, they’re both HD,” but how many will buy on name alone?

Never mind that the name itself looks (and sounds) like blurry. Not what you want to hear when dropping a lot of money to replace a bunch of movies you bought in SD a few years ago.

And so the studios might be slitting their own throats. Movie attendance is down over the past several years. Partly movies are kind of boring now, also suspense and action movies keep dancing around what’s really scary. But the studios now want consumers to re-buy movies they just bought. The great DVD migration wasn’t that long ago, most DVDs were probably purchased within the past 5 years. But now Hollywood wants everyone to buy those movies yet again, and they’re going to spend a fortune on conversion and manufacturing in a bet that consumers will buy the new disks. And if we don’t? Lots of bankruptcies.