Nat's Hollywood Christmas (1956)

Presented on the show as historical proof that entertainers objectified women long before hip-hop, this black-and-white piece imitates a 1956 Nat King Cole holiday broadcast. Nat croons a carol and warmly thanks his viewers, then turns to the woman seated beside him and trades the seasonal greeting for an insult. As his tuxedoed entourage passes him bottles, he pours champagne over her while she shimmies in her chair, brags about how aroused he is and about the premium bubbly his King Cole Records crew drinks, and signs off by cursing at the audience and promising an even raunchier eggnog stunt next year. The joke comes from grafting rap-video excess onto the polite conventions of a vintage TV special.

On the show, Chappelle introduces the piece as footage he dug up to prove that women were being objectified long before hip-hop. IMDb lists the segment as "Old Time Booty Video: Nat King Cole".