Everyone wants a piece of Hassaan Mackey. Old friends who haven't been around for years, fans who insist they've been listening since day one, and industry reps who finally want to give that old mixtape a listen. Inevitably, each came with Mackey's shot at national exposure and potential fame.
On Friday, Nov. 6, the Rochester resident will appear on BET's 106 & Park "Freestyle Friday," giving him the chance to showcase his skills on a program that routinely draws more than a million viewers, according to Nielsen Media Research. And while Mackey says that most of the people around him are hyped up about it, he isn't quite feeding into it.
Mackey may be one of Rochester's most compelling figures with a microphone in hand, but offstage, he's an introvert who says he couldn't care less about the glitz and glamour that a lucrative rap career would bring. Mackey has more pressing things on his mind.
"What I really want to buy are headstones for my mother and my sister because their grave sites don't have them," he says. "To me, that's more of an accomplishment than any of the other shit that I could possibly do at this point in time."
Beneath the raspy voice and socially conscience rhymes is a man whose life has been marred by death and disappointment. Born and raised on the city's west side, Mackey was the youngest of five siblings raised by a single mother.
When he was 5, his 17-year-old sister, Tanya Lester, was killed during a domestic dispute with her boyfriend; Mackey didn't go into the details. When he was 11, his mother, whom he called his "best friend," lost her fight with sclerosis of the liver, a disease she suffered from for most of Mackey's life.
Both are subjects Mackey rarely talks about. In fact, he's written just one song about it, titled "Grace" (named after his late mother, Grace Lester), from his 2006 album, Soul For Sale. He rhymes: Knowing she would soon be heading towards the sky/ (I was) Praying to God for her to get well in due time, but it never happened.
Around the time of his mother's passing, Mackey found himself growing closer to his father, William Mackey, from whom Hassaan previously had been estranged.
But a year after Mackey lost his mother, his father died in his sleep of a heart attack, which was brought on by the diabetes he had battled for a lifetime.
Over the next few years, a young Mackey bounced around, living with different family members and struggling to find an identity. "It was like, I didn't have nobody," he recalls. "It felt like I was raising myself, mentally."
Mackey found solace in music. He'd been a fan of hip-hop since he was in the first grade, when he began listening to the likes of Whodini, Soulsonic Force and UTFO. And at 13, Mackey started writing his own rhymes. His thought-provoking and creative wordplay earned him the nickname PHILLY (Putting' Heart Into Lyrics, Life, and You) from his older cousins. By the time Mackey graduated from Franklin High School in 1998, he had made a name for himself on the local scene.
"He's always been one of Rochester's top MCs," says 29-year-old Ben Gonyo, one-half of DJ duo Discolobos, which hosted open-mic nights at Java's Café from 1999 to 2004.
"Hassaan has endured a lot of tough times, and rapping has always been his primary outlet," Gonyo adds. "Of any Rochester MC, Hassaan is the one whose career should take off."
Things looked promising for Mackey in late 2006. Hip-hop label Rawkus Records (Mos Def, Talib Kweli) chose Mackey, along with 49 other underground rappers, for its "Rawkus 50." The promotion was meant to provide marketing opportunities for each of the acts. However, as Rawkus became less of a force in the music industry, Mackey says the promotion never really took off.
"I was disappointed in the fact that they didn't do everything they said they were going to do," says Mackey. "Rawkus wasn't what it used to be. It was just bad timing."
Mackey's music has always combined the ferocity of old-school lyricists like Rakim or Kool G Rap with soulful instrumentals. His songs have never really mirrored what's been mainstream. And those who know Mackey best say that he's remained true to himself.
"He sticks to what he does and who he is," says his girlfriend Kia Sloan, 32, of Rochester. "He doesn't let anyone else tell him what he needs to do to be on top. He's very inclined with his heart and with his music and does not stray too far away from it."
In the past few months Mackey has appeared on New York City's Hot 97 radio station twice and made several appearances on OkayPlayer.com, a Web site co-founded by The Roots' drummer Ahmir "Questlove" Thompson.
Mackey holds down two jobs — one at Record Archive and one at a factory in Penfield; he's taking a leave of absence from the factory job to participate in "Freestyle Friday," which, if he's successful, would involve future appearances. He got the chance to appear on BET after he won a freestyle competition on Sept. 12 at Venu Resto-Lounge & Nightclub.
He says that part of him can't wait for the 106 & Park hype to be over. While he sees the opportunity as a valuable tool in his musical journey, he seems more content in using this time to reflect on what he's been through and to accept what may or may not lie ahead.
"Everything comes in God's time," Mackey says. "Someday I'll come across the right person at the right time, but who's to say when that will happen. Honestly, if I could have anything, my mother would be sitting here listening, right along with my sister and my father. All that other shit will come when it comes."



