1.) Rare 1985 Japanese Laserdisc:

(click image for full size. Source: Walt Disney Japanese Laserdiscs)
I like the psychedelic colors of this one, even though the art is a little loopy. It’s quite dynamic and it certainly catches your eye.
One problem - the image on the left on the back of the laserdisc sleeve definitely refers the Tico-tico no Fuba dance, which is from Saludos Amigos, not The 3 Caballeros. These box layout people didn’t do their research.
2.) 1994 Japanese Laserdisc
This had virtually the same box art as the 1995 VHS release…they didn’t even bother to reformat, just slapped it on the cover and put some yellow space around it. (Pictured here)
3.) The 1995 VHS Release

Pretty corny, but it could be far worse. At least this was made before the days of shiny-fied digital “3D art,” which sometimes comes out strangely.
4.) The 1995 Laserdisc Combo Set:

Almost the same as the 1995 VHS release, but more “elegant” to target the highbrow laserdisc machine owner (I hear those things were notoriously expensive). This edition had a ton of extras, and many still haven’t made it onto the DVD releases.
5.) The 2000 VHS/DVD:

This cover is my favorite by far, although the desert-like landscape looks more “Lawrence of Arabia” than “Latin America.” I think this is quite nice, especially when compared to the *other* covers.
6.) The 2008 DVD Combo Set:

I really dislike this one a lot. First of all, it recycles the 2000 box art from the two films; I can’t say the box art for Saludos Amigos was too great, and it’s a shame to see it here, asserting its dominance over the much nicer Caballeros box art. I really can’t stand Jose Carioca’s “anti-gravity” hat here…what were they thinking? They made an effort to incorporate both films into the cover, but what they came up with really stinks. The text is too big and quite unsightly, and I can’t stand the “HEY LOOK BARGAINS 2-FOR-1!” banner on the bottom. I would have rather seen new art….or utilizing some of the amazing poster art from these films.
So, what are your opinions? Which is your favorite? Do you have other ideas?
If anyone has any different bootleg or alternate cover art not mentioned here, post the image links in your comment!
***Additions 6/17/2008 (courtesy of Foxxfur)

Box art for a reel of 8mm film of the “Three Caballeros” song number. I really like this box art! I wish they’d have used this instead of some of the others! The colors/design are a bit off on Panchito, though.

Very grade-school-library-looking….. This is a VHS from the ’80s using box art similar to the ‘85 Japanese laserdisc, but without the technicolor rainbow horizon.