1. Sugar Ray f. Supercat, “Fly”
Supercat is the king of this shit, as in so many other obscure categories (Best Indo-Caribbean artiste, Best Remix, Fewest Pauses for Breath and a couple of catty-gerries too gangterish to mention…) but this track wins on both randomness and addictiveness. I will never forget driving around Port Antonio ca. 1999 when this came on the radio, only to have my guide Chilly Famous jack up the volume and say “You know this tune?? BAD.” Not bad meaning bad, but bad meaning wicked.