“Dirty Diana” is the 5th single (and 5th #1 song) from Michael’s 1987 album Bad, which sees him tackle the issue of groupies in a more aggressive, palpable way than he did on “Billie Jean”, accompanied by a scathing guitar riff a la “Beat It” (featuring guitarist Steve Stevens).
On the song, in an interview in 1987 Michael said:
I love Dirty Diana, it’s one of my favorites. It’s a life story of a groupie – I hate to say the word groupie, but that’s what it is – and it’s something that I’ve experienced, and a lot of people that grow up on the road [experience].
On a visit to Wembley during his Bad World Tour in 1988, Michael took this song out of the lineup in deference to Princess Diana. It was previously thought that the song was not performed that night, but it was in fact added back into the set list shortly after hearing that it was one of her favorite songs.