First Hit #1: July 2, 1988
Michael Jackson has always had a weird relationship with sexuality, and Dirty Diana is probably the best example of this in his catalog. It’s about his efforts to brush off a groupie, but it’s presented in a way that recalls a horror movie, rather than a mere brush off of an unwanted lady. The brooding synths, the intense guitar, the general anger in the lyrics. She comes across not as someone who merely wants to make it with musicians, but as an almost spectral presence, a figure of sexual violence that hunts her prey and tries to corrupt the innocent – like Jackson, for instance. It’s got a new sound from him, something that’s a bit darker and more intense than his ordinary pop stylings, but it’s still strange to have someone so afraid of her advances. Diana isn’t just a groupie, she’s almost sex in all its forms, and in spite of being a pop star, Jackson doesn’t quite know what to do with sex or the desire to have it.
Also, holy moly, he owns all the belts in the video, doesn’t he?