13. Doug E. Fresh and Slick Rick, "La-Di-Da-Di"
Eye-patched British-American rapper Slick Rick was still known as MC Ricky D when "La Di Da Di" was released in 1985. Rick spins a rude 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 (name-checking Gucci, Bally, Kangol, Polo, Johnson's Baby Powder and Oil of Olay), it would be referenced endlessly – most famously in the chorus of Notorious B.I.G.'s "Hypnotize." It also started the trend of rappers breaking into off-key song. "La-Di-Da-Di" began as a live routine that turned into a sensation. "Doug E. used to carry me around with him," Rick recalled. "The crowd ... first they would look at you like, 'Whatever, skinny nerd trying to get put on,' but then when you kicked the humor and they got to laughing and enjoying themselves, it sold itself."