The transition between Bad and Dangerous (Literally the year 1990) has always been the most intriguing for me when it comes to Michael Jackson.
That's a pretty bold thing to say considering his illustrious body of work over the years, but this is a topic I've always wanted to discuss; so please, indulge me for awhile.
As others have noted on page 1 of this thread, Michael's appearance changed rather dramatically from 1991 to 1992 as his skin lost all traces of it's former birth color. If you look at the projects (so significant that yes, I'll go there and say those initial single releases were projects on their own) starting with Black or White, Jackson was taking the discussion of his race, and the inherent racism that came with it to task. The worst disease of our times, race was still dividing so many people in the early 90s, and Michael seemed to be at the epicenter, undoubtably the most popular person on Earth at the time period.
I've always gotten the impression that he struggled with letting go of the former sense of self that came from looking upon his reflection and seeing someone of darker complexion. That's conjecture on my part, but from what we know apparently Michael was applying heavy makeup to retain a vaguely similar aesthetic to that of his youthful self. Personally I've seen pictures of him in 1989 looking darker than 1985 and 1986 circa Captain EO.
Perhaps he was frustrated with the reality that the vitiligo was going to overtake his efforts very soon. The Song Black or White strategically sees him address this. Gone are the Bad era curls and buckles, Mike had embraced himself as a human living under strenuous conditions, as we all do, and presented a man who didn't care about the labels we fix to each other. It's the last time there was any distinct tanned complexion to his look.
Interestingly enough, I've always felt the song was geared for White people, just as Remember the Time is for Black people. In the former we see the child blast his middle aged father back to Africa for a lesson on culture (NOT race) whilst Jackson, Black in heritage, sings over guitar riffs and metal interludes. He even has Bill Bottrell, White in heritage, deliver the rap and rhyme "I'm not gonna spend my life being a color".
The often misheard lyric of "If you're thinking about my baby it won't matter if you're black of white" suggest that no matter if you're the suburban father in the Black or White video, or the former friends featured in BAD, if you dare question the validity of my relationship(s) on the basis of race, your butt is mine!
On the flip side, In Remember the Time Michael debuts a look that contrasts sharply to the other African-Americans featured in the film. With skin devoid of seemingly all pigmentation, long flowing hair and a benchmark on his personnel androgyny, Jackson had become the opposite of what most Black Americans at the time even considered "Black" or masculine. And yet, he still delivers the most powerful soul man singing of his career on the track. So I guess I never saw it as BAD Era or Dangerous Era when it came to his looks,it was just the same guy refining his craft. The genesis of this train of thought, I think, was in 1990.