50 Cent - “In Da Club,” one of the most ubiquitous hip-hop songs of all time.
A Tribe Called Quest - “Scenario,” perhaps the ultimate posse rap.
Afrika Bambaataa - “Planet Rock,” a funky, futuristic ride that pianist Jason Moran has turned into a jazz number.
Beastie Boys - “Hey Ladies,” which stomps on the thin line between brainy and bratty.
Biz Markie - “Just a Friend,” which took warbling to unprecedented heights.
Dr. Dre feat. Snoop Doggy Dogg - “Deep Cover,” the track that launched one of rap’s most successful collaborations.
Missy Elliott - “Work It,” which further cemented this playful MC’s place as a must-watch innovator.
Eminem - “Lose Yourself,” one of the most lyrically virtuosic performances ever laid down and the only rap song ever to win an Oscar.
Eric B. and Rakim - “Eric B. Is President.” Rakim ran on the platform that he’d “never let the mike magnetize me no more,” and the hip-hop electorate voted him a titan.
Grandmaster Flash - “The Message,” which, early on, recognized hip-hop’s power as a soapbox.
Jay-Z - “Hard Knock Life (Ghetto Anthem),” which connected the dots between the street corner and Broadway.
LL Cool J - “Rock the Bells,” one of hip-hop’s longest-running talents getting warmed up.
MC Hammer - “U Can’t Touch This,” a mega-hit that helped push hip-hop into the commercial big time.
Nas - “The World Is Yours,” one of hip-hop’s most ferocious stylists lets loose on his classic “Illmatic.”
Naughty by Nature - “O.P.P.,” a sexually charged single that defined a mentality and launched a catchphrase.
Notorious B.I.G. - “Big Poppa,” which announced the arrival of a hip-hop heavyweight.
N.W.A. - “Straight Outta Compton,” one of the earliest songs in gangsta rap history, and still one of the most incendiary.
OutKast - “B.O.B.,” a thrilling political song you can dance to. (Try naming another one of those, in any genre.)
Public Enemy - “Fight the Power,” an anti-establishment landmark.
Queen Latifah - “Ladies First,” a big step forward for female rappers.
Run DMC - “Walk This Way,” which kicked down the wall between rock and rap.
Salt-N-Pepa - “Push It,” the MTV hit that upset hip-hop’s man-in-charge dogma.
Slick Rick and Doug E. Fresh - “La Di Da Di,” the “Ulysses” of hip-hop, it’s a story about one man’s tragicomic journey through a tumultuous day.
Sugarhill Gang - “Rapper’s Delight,” a dated party song that, despite its hokeyness, still matters because it came first.
--- Contributing: Sonia Murray and Phil Kloer