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CBC Features the Storied History of Jacky Jasper

The history of hip-hop is littered with references to pimp culture, and has essentially made the idea of being an agent for prostitutes seem fashionable. The pimp persona that was popularized in Iceberg Slim novels can be found anywhere, from rapper Ice T and Too Short to Snoop Dogg’s spiritual advisor and ex-pimp Bishop Don Juan, to others like the late Pimp C (of legendary UGK crew), who even incorporated it in the naming process. When 50 Cent rhymed that he was a “P.I.M.P,” it zoomed to the top of the charts, though he wasn’t being literal
.But what happens when you’re a rapper who really was one? For Jacky Jasper, the artist formerly known as H Bomb (and HDV before that), translating the street hustle and pimp life to celluloid was never easy, being based in a safe, conservative city like Toronto. “From when I was 14 to 15 years old, I used to go down to George Harvey Collegiate Institute, or various projects like ‘the Jungle’ (Lawrence Heights) … and after school we’d go shoplift at the Eaton Centre … terrorizing Le Chateau and different various stores, just to stay in fashion as kids going to school,” explains the Grammy-winning artist. Jasper, whose “Proud Ta Be Pimpin’” song from his sophomore Higher Deeper Values release laid out the pimp game blueprint. “I learned from having gear to taking gear to selling gear,” he continues. “So now I’m selling stuff to people in schools, I’m getting money off sales. I got pretty good at it.” Jasper says he got so good at this hustle that he was easily making $500 a day shoplifting as a kid. Then crack cocaine hit the local scene. Hard. “I was 17 hanging out at after-hours clubs near Yonge and Dundas Street,” says Jasper. “I saw pimps. And I never really understood them, but I was looking to understand the game.” Dope deals and rhymes Having grown up watching black blaxploitation movies like The Mack and Trouble Man, it’s not like this lifestyle was something Jasper (known in the streets as Hollywood) hadn’t seen before. His intrusion into this netherworld began with him selling a leather coat to a pimp, and then turned into him dabbling in substances, which was not unusual in the Toronto urban street culture of the ’80s. Jasper’s lifestyle was taking a toll on him both socially and physically. “I couldn’t bring my money home, because mom would ask too many questions,” he says. The spending sprees included consuming drugs, and he admitted that, “you start hurting yourself. You think you’re partying but you’re destroying yourself.” When word got out about Jasper’s exploits, a warrant was issued for his arrest, and by that time he had moved to the Lawrence Heights neighbourhood (affectionately referred to as “the Jungle”), he did the wise thing and turned himself in. After doing less than a year in East Detention Centre, and engaging in a necessary detox process, Jasper hit a crisis as a 20-something young black male, and asked himself: “What am I gonna do when I get out?” The new ideas for a lifestyle change and hustle were to be found on MuchMusic’s infamous Electric Circus. “I walked out of my cell one day and I saw Michie Mee and [King] Lou [Dream Warriors] on Electric Circus, and I said ‘I could do that,’ I’ve been doing it all my life … we were the original B-boys of Toronto,” says Jasper. “I started writing jail stories from different inmates that was telling me their stories.” Jasper had no intention of going back to the street life, so he took a temp job through Kelly’s and saved up some money. After picking King Lou’s brain, Jasper went to seek out record label impresario Ivan Berry, whom he had known from high school, and who headed the upstart urban indie label Beat Factory. An A&R representative from the ISBA/Sony label, who was rooted in punk, heard Jasper’s authentic street tales, and before the rapper knew it, he was signed to a recording contract. But all parties involved were in for a rude awakening, over a bevy of issues. “I’m coming from the streets, and I went in the booth and started saying mother f–k this, b–ch that, because that’s my reality,” explains Jasper. “Loads of content to draw on from pimping.” Part of Jasper’s life, one could argue, loosely mirrors Terrence Howard’s character DJay in the Hollywood flick Hustle and Flow,, set in the world of Memphis hip-hop. But Jasper soon found out that this new music hustle wasn’t quite rewarding him with enough dough, despite his deft rhyme flow. “So now I’m thinking, ‘you’re getting signed, you’re getting some money,’ and I had a rude awakening,” he says. After the 1990 release of his aptly titled debut Sex, Drugs + Violence, the money wasn’t coming in as Jasper had expected.