#14: Kool Moe Dee
"How Ya Like Me Now," from How Ya Like Me Now (1987)
Rap legend Kool Moe Dee didn't pull any punches on his sophomore album. No, really: He didn't pull any punches. Though he enjoyed a ton of success off the strength of the album's second track, "Wild Wild West," the NYC rapper actually started the album with this song, which contained a flurry of jabs at Kool Moe Dee's longtime adversary LL Cool J. Ouch.
#13: LL Cool J
"I'm Bad," from Bigger and Deffer (1987)
Speaking of LL Cool J, the Queens rapper knew a thing or two (we say two, because—spoiler alert!—he'll have another entry on this list later) about making a strong first impression. He certainly did it on his second studio album, Bigger and Deffer, when he kicked things off with the album's first single, "I'm Bad." But in this case, that was bad meaning good. Really good.