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Big Daddy Kane was undoubtedly one of the finest MCs of his era, bringing a level of verbal dexterity only matched by fellow legends such as Kool G Rap and Rakim, but with the added advantages of a dry sense of humor and a truly athletic stage show. Among his timeless Brag Rap classics such as ‘Raw’, ‘Set It Off’, ‘Ain’t No Half Steppin’, and ‘Long Live The Kane,’ King Asiatic Nobody’s Equal also wanted the world to know that he was a ‘Smooth Operator’. Ever since his debut album, which pictured him clothed as a Roman emperor being attended to by a trio of comely servants, he made sure to include at least one love ballad. This was standard issue for hip-hop albums in the mid to late eighties, in much the same way that 1989 saw the majority of rap albums including a hip-house jam. But as time wore on, the Big Daddy began to go above and beyond just providing the token song ‘for the ladies’ and seemed to follow a career trajectory determined to position him as rap’s answer to Barry White.

His sophomore album, It’s A Big Daddy Kane Thing, starts off with a powerful trio of tracks in the tradition of other top-heavy masterpieces such as N.W.A.’s Straight Outta Compton and Eric B. and Rakim’s Follow The Leader. As it progresses, the record branches out into a new-jack swing excursion, a hip-house DJ cut-up track and another ballad, the abysmal ‘To Be Your Man,’ which amusingly opens with Kane hanging out with his crew in the dressing room, rubbing lotion on his legs while only dressed in boxer shorts. Pause. The LP had enough strong tracks to allow fans to overlook this cheesy attempt at a love song, as BDK kept providing fans with dope songs like ‘Warm It Up, Kane’ and ‘Mortal Kombat.’

Things began to go off the rails in 1990, with the Taste of Chocolate album featuring a duet with (you guessed it) Barry White. Kane was so thrilled to be joined by the smooth jam veteran that he released the song as a single with this accompanying creepy video where BDK whispers that he wants to ‘taste you from your lipstick to your toenail polish’ in between lounging about his apartment in silk pyjamas and trading tips with Mr. White regarding matters of the heart. This wouldn’t have been a deal breaker if Big Daddy Kane would have offset this with his usual allocation of Brag Rap bangers, but the remainder of the largely self-produced LP found him increasingly focused on convincing us that he was the ultimate ladies’ man.

The wheels completely fell of in 1991, when Kane delivered his fourth album in as many years. By this stage he’d almost completely abandoned the powerful lyrical displays of his earlier work in order to pursue crossover chart success, as ‘The Lover In You‘ demonstrated with its insipid video and lazy track (a loop of Prince’s ‘Pop Life’). Once again, the Big Daddy reminds us of his fondness for ‘licking toes’ and wearing garish suits, but with only a handful of traditional rap tracks on the LP, only the most devoted of his fans were still listening. When news of his Playgirl magazine pictorial hit the streets that same year, rap listeners everywhere were shaking their heads with disapproval, only to have Kane’s appearance in Heavy D’s star-studded ‘Don’t Curse‘ video put the final nail in his reputation. With his arm in a sling and sporting a tight purple outfit that even the aforementioned Prince would have second thoughts about wearing, Big Daddy Kane was described as resembling ‘a broke pimp.’

At this point, the rap world seemed to abandon Kane altogether, as he increasingly failed to deliver enough memorable records to excuse his increasingly questionable moves outside of the studio. Still, it wasn’t all bad for the guy who often called himself ‘Dark Gable,’ as 1992 saw him getting busy with Madonna and Naomi Campbell in the highly publicised Sex book. He used this time to lick his wounds (instead of feet) and regroup, so that when he returned with new music the following year BDK ditched the suits and returned to the ‘street’ look of his early days. Employing the talents of the up-and-coming Trackmasterz, Kane finally regained some of the fire that he had in his Marley Marl glory days and won back some of the doubters.

Unfortunately, by the time the sixth album was released on a new label (MCA) in 1994, the hip-hop world had well and truly moved on, as Nas, Biggie Smalls, and the Wu-Tang Clan had the game on lock. Daddy’s Home has its moments in retrospect, but at the time it seemed like a relic of a bygone era. Even with contributions from DJ Premier, Easy Mo Bee and Ol’ Dirty Bastard couldn’t save it from a speedy trip to the dollar bin. Kane released his final solo album in 1997, and has since stuck to touring and guest features.

Where did it all go wrong? In some ways, Big Daddy Kane may have been too far ahead of his time. Much of his love for corny outfits and sappy pandering to the female audience was no worse than some of Drake’s antics, but it was an earlier, less-forgiving time, without the benefit of ironic memes. That being said, LL Cool J and Heavy D proved that it was possible to navigate that same thin line between being ‘rap heartthrobs’ while still maintaining the respect of their male fans. The problem for Kane was that once he relied too heavily on his own production talents, the hits seemed to dry up. Music fans are willing to forgive pretty much anything if you keep supplying them with that work, as R. Kelly has proven. If only Big Daddy Kane had been able to outweigh the purple suits and toe fetishes with a steady stream of classic songs during those later albums, perhaps his career as a recording artist would have lasted longer.

Keep up with Robbie’s weekly ‘No Country for Old (Rap) Men’ here.