Madonna on Letterman in 1994.
Letterman comes undone for being sleazy and invasive with his humour. Madonna, clearly stoned off her face sort of tries to take him to task for it, but just ends up swearing a lot and seeming like a complete dripping non-gender-specific genital. It's so long and nothing that David does can save the interview. Even though it's clearly why she's riled up, he still makes sporadic references to her sex life throughout the video. Real stomach clencher.