It is almost impossible to state just what De La Soul meant (and means) to me. They simultaneously challenged me to own my difference and invited me to celebrate it. Granted, De La were part of the very divisive idea the "Golden Age" of hip-hop, but they were so far removed from any of their contemporaries--even from their Native Tongue bredren, The Jungle Brothers, who dropped Straight Out the Jungle the year before De La's debut, 3 Feet High and Rising.
College radio--for a long time--was very important to and for hip-hop and co-signed De La in a way that gave De La the exposure they deserved, while also setting them against other hip-hop groups--almost like an antidote to this other publicly expressed Blackness. Too Short and Tone Loc dropped albums in January of that year: One hyper-misogynist and street, the other radio (read: accepted by white people) friendly. De La dropped on March 14th, 1989 and the hip-hop landscape was changed. If not for everyone, then, certainly for me.
We were at the beginning of what many would call the "crack era" and hope was being leeched from our communities. It was fast money, fast cars, and little to no concern for life. My brother in letters, Michael A Gonzales, wrote this and you should read it, if you want an intimate picture of what I'm describing here.
What was missing, for me, was whimsy. This time in hip-hop (and Black and Latin culture) was analogous to the hyper-violent/anti-hero/nihilist stretch in comic books. DC Comics' Lobo character, a character who was meant to take the piss out of the whole violent anti-hero became one; Marvel's The Punisher and Wolverine, all of the first gen Image Comics stuff--absent of hope, just like a good portion of hip-hop music.
This isn't to dis the hip-hop music of the time, because those stories were real, valid, and vital, although not very pleasant to some. De La Soul (as well as the other members of the loose confederation dubbed The Native Tongues by Kool DJ Red Alert) redefined Blackness, but more importantly to me, the redefined Black Cool.
Back cool is damn near whatever you, as a Black individual, want it to be. Some folks are afrofuturists, some re/claim their ties to Africa, some adopt Caribbean vibes, and some, like De La Soul, were AfroRetroFutureWhimsical and it was just what I needed.
Here are a few more examples of the black whimsical impulse: