Inspired by the ranking in "The Rap Year Book" written by Shea Serrano.
The year refers either to the year the track was published or perhaps the year it was published in an album.
"Greatest" song does not necessarily mean the best selling one but more importantly the most influential one and of course this is debatable so you might agree with some and less with others but nevertheless it will be a journey through Rap History.

1979   

"RHYMIN' AND RAPPIN"
PAULETTE AND TANYA WINLEY

They recite braggadocio rhymes over a repulsive, soulful groove that is far less disco fever than uptown park jam. Absent the polished, commercial sheen of other early rap recordings, this one says more about Hip Hop's break beat-driven origins. The Winley sisters were undoubtedly the First Ladies of Hip Hop.
Paul Cantor


1980

"THE BREAKES"
KURTIS BLOW

The song helped take rap from the freewheel rambling that it was and gave it structure by instituting a chorus. It was the first rap song that had a hook, which is to say it was broken up into easily digestible sections..
"All the significant records at that time had emcees rhyming continuously with a music break to break the monotony. So, in a sense, Kurtis Blow showed us how to write songs cause if there's no hook, there's no song.
Kool Moe Dee


1981

"JAZZY SENSATION"
AFRIKA BAMBAATAA AND THE JAZZY FIVE

 

What you hear are the first whispers of rap moving away from the disco or funk and towards the energetic electro-funk that Bambaataa would become most famous for.


1982

 "THE MESSAGE"
 GRANDMASTER FLASH AND
 THE FURIOUS FIVE

 

It was the moment that rap gained a conscience, the moment that broadened what rap was (and would eventually become), the moment that rap hinted at the social significance it could (and would) carry. 


1983

"SUCKER M.C.S"

RUN-DMC

 

This record marks dual points in rap's evolution. It is when rap parted itself between old and new school for the first time and it is also the first time a song could be described as "Battle rap".