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And I can't believe people are in here naming early examples of rappers featuring on songs, etc, yet are completely forgetting about this little legend from way back in 1984 (especially since it was a #1 UK hit!):

Some of us have made a lot of effort to forget the existence of Chaka Khan :puke2:

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Ok I know this wasn't a single but the most shocking early example I remember is a song called 'One Boy Girl' on Kylie's 'Rhythm of Love' album which was released in 1990. It was only her 3rd album and she was still doing pretty cheesy mainstream pop, and I remember buying the album and half way through this song, some woman starts rapping... and then if that wasn't weird enough (cos it was pretty weird at the time), Kylie then joins in with the rapping!! And remember this was many years earlier than the likes of J-Lo, Mariah etc!

 

Oh and it's also one of the most cringeworthy raps ever!

 

For those who don't know it (the rap starts at about 2:45):

 

Edited by mango7

R.E.M. had a rapper (can't remember his name) do a verse on "Radio Song" in '91, that was pretty rare in the alternative rock scene then.
Ok I know this wasn't a single but the most shocking early example I remember is a song called 'One Boy Girl' on Kylie's 'Rhythm of Love' album which was released in 1990. It was only her 3rd album and she was still doing pretty cheesy mainstream pop, and I remember buying the album and half way through this song, some woman starts rapping... and then if that wasn't weird enough (cos it was pretty weird at the time), Kylie then joins in with the rapping!! And remember this was many years earlier than the likes of J-Lo, Mariah etc!

 

Oh and it's also one of the most cringeworthy raps ever!

 

How could *I* possibly tell that, though... :P

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