I submit De La Soul’s Ghost Weed sketch (first episode in a series) as not only one of the best in hip hop, but one of the best in the history of sketch comedy. It’s not lol-funny; it’s just dope. And the spirit of it is comedy in the most romantic sense.
De La and Prince Paul might be the singular example of character sketch-comic genius in hip hop. Em, Kanye, Jay, as examples, can be very funny. But it’s lines in the song, or the song itself. No one remembers their interstitial sketch stuff. But De La’s sketches with Prince Paul (first two albums mostly) are on some straight quirky-details-postmodern-wes anderson-meets-Tracy Jordan-urban-inanity bananasness. When Vanilla Ice was pop and not a joke, they were the ones making the jokes. Hip Hop humorists before hip hop was even old enough to have a sense of humor.