13. Doug E. Fresh and the Get Fresh Crew, 'La Di Da Di'
Non-album single, 1985
Eye-patched British-American rapper Slick Rick was still known as MC Ricky D when "La Di Da Di" was released in 1985. He spins a Mrs. Robinson tale of being hit on by his ex-girlfriend's mom, while beatbox pioneer Fresh provides backdrop. A milestone in rap storytelling (and product placement: Gucci, Bally, Kangol, Polo, Johnson's baby powder and Oil of Olay), it would be referenced endlessly, most famously in the chorus of the Notorious B.I.G.'s "Hypnotize," and most thoroughly in Snoop Dogg's "Lodi Dodi," a weed-obsessed cover version. It also began the trend of rappers breaking into off-key song – although Rick's detour into A Taste of Honey's "Sukiyaki" was later edited out for copyright reasons.