In the midst of rap’s late-’80s golden age, Big Daddy Kane introduced a new duality to the role of MC, proving that hardcore word assassins could also be smooth casanovas. Born in Brooklyn in 1968, Kane rose up with Marley Marl’s hip-hop collective Juice Crew and became a New York rap fixture thanks to his indomitable lyrics, as showcased in his contributions to fellow Crew member Biz Markie’s 1988 debut, Goin’ Off. Later that year, he released Long Live the Kane, demonstrating his magnetic versatility with the confidence of “Ain’t No Half-Steppin’,” charm of “The Day You’re Mine,” and pro-Blackness of the title track. By his sophomore album, 1989’s It’s a Big Daddy Thing, Kane was not bound to any particular formula. He welcomed Teddy Riley’s new jack swing flair on “I Get the Job Done” and produced “Smooth Operator” himself, juggling five other samples over Mary Jane Girls’ “All Night Long.” After modeling for Madonna’s Sex photo book, Big Daddy Kane became the ’90s’ ultimate provocateur. His legacy reverberates in every rapper with the desire to make hip-hop sexy.