Listen to SUMMER MADNESS by Kool & The Gang.
Listen to SUMMERTIME by DJ Jazzy Jeff & The Fresh Prince.
Everybody knows this one. Seriously, I've always loved Summertime (and especially the video). Funny, because DJ Jazzy Jeff & The Fresh Prince were basically a spent force by 1991 (it had been three years since their comedy kidz classic, "He's the DJ, I'm the Rapper"), and I don't think anyone I knew owned up to liking them in 1991, not with gangsta rap coming to the fore.
Still, Summertime was a masterful single, and it represents all that was good about hip hop's classic period. Two things: first, it rides a big, obvious sample (though the original song is still worth hearing in its own context), in a way that was rapidly becoming prohibitively expensive for most hip hop artists. It stops getting fun spotting samples from the mid-90s on when you're looking for a two-second loop from an out-of-print Hungarian beat combo, know what I mean?
Second, Will Smith was one of the last emcees who didn't front about being a not-very-good rapper. So many of those great hip hop singles from the mid-to-late 80s, early 90s had some atrocious rhymes on them, and nobody cared. It made them endearing, in fact. These days, you still have terrible rappers on hit records, but they've all got to pretend they're something special. Not Will Smith, though. He had no problem dropping clumsy stuff like "And this is the Fresh Prince's new definition of Summer Madness." Oof. (That line in particular has a proud pedigree: a sixth grade-style concluding sentence "And that's why George Washington was our first President" used to be a respected way of wrapping up hip hop verses (like, every Eazy-E song ever), before people got too embarrassed).
...After I wrote the above, but before it was published, Salon posted an article complaining that "Hip-hop is no longer cooler than me" by some guy from Iowa. I don't really have much to say on it, I think it's a pretty dumb piece, but it's interesting he's got almost a completely opposite take on hip hop history than me. (To be fair, he's talking about more recent developments and I don't have much of an opinion about contemporary hip hop either way anymore, except to say that some old guy going on about how the kids music these days is stupider than it used to be = wasting everybody's time.)
Photo: Mural detail (4).