If it’s not already documented at Know Your Meme or Wiki article on “Know Your Meme” (I haven’t even checked myself) perhaps you could do it yourself or urge those guys to add it to their archives.
In fact time has yet to really dovetail back in with them.
Around 1988-1991 there was a whimsical side to hip-hop that was cresting: the Digital Underground (“Humpty Dance”, “Dowhatchalike”), Naughty By Nature (“O.P.P.”), Sir Mix-a-lot (“Baby Got Back”), Tone Loc (“Funky Cold Medina”), Young MC (“Bust A Move”)… Other seminal songs like “Rapper’s Delight” by the Sugarhill Gang or “Jam On It” by Newcleus had more than a few smile inducing lines as well.
Then Dr. Dre, Snoop Dogg, Tupac, Biggie Smalls, etc., took over and for a long time, rap was (is?) mostly dominated by gangsta style lyrics. The most recent hip-hop/R&B hits I can think of that made me laugh or smile (not counting the pained eye-rolling type) would be, hm, maybe Eminem’s “Just Lose It” and Shaggy’s “It Wasn’t Me” (which I’m SURE was one big reference to the Eddie Murphy standup routine from the 1980s).