Getting close: Hip-hop artist Freddy Jackson climbs higher with a revamped sound

You can witness the rise of hip-hop artist Freddy Jackson every third Thursday of the month at BON, while he’s still playing small venues. He will hold an album release party for Frederick on June 18. Photo: Martyn Kyle You can witness the rise of hip-hop artist Freddy Jackson every third Thursday of the month at BON, while he’s still playing small venues. He will hold an album release party for Frederick on June 18. Photo: Martyn Kyle

When you walk into Freddy Jackson’s home studio, you are immediately greeted by the legends that influenced the Charlottesville-based musician, and helped to cultivate his diverse taste in music. His walls are covered with images of Bob Marley, Kurt Cobain, Parliament, Jimi Hendrix, Betty Wright—and he even gets down with a little Elton John. Although Jackson’s repertoire has evolved from funk groups like Confunction, Parliament, and the crazy clothes and music of George Clinton, it’s hip-hop that describes his current sound.

The music seed was planted in Jackson’s childhood when his father, a former club owner, would have parties at their home in Buckingham, Virginia. Those early memories laid the foundation for his creativity. “I remember hearing all this noise and people talking and laughing during those parties, and my dad played everything from Quincy Jones and Smokey to Parliament and Marvin Gaye,” said Jackson. He pointed to the wall in his studio. “I think that’s the foundation—that’s where I get it from,” he said.

While his dad exposed him to musical style, Jackson attributes his love of performing to his mother, who insisted that he attend church on Sundays after spending time in the clubs with his father on Saturday nights. As a result, he started playing the drums and singing in church at a young age and he’s managed to incorporate both parents’ influence into his sound.

Now, with four hip-hop albums to his credit: Music Money Love Hustle, Jackson aka Freddy Krueger, the self-titled Freddy and The 4th Quarter, Jackson looks to his upcoming release Frederick (June 18) for that push to bigger success.

Jackson has been climbing the ladder for the past six years, growing a fan base, and making his name known through distribution deals and press exposure—he was featured in the music biz book Hottest New Artists in 2014.

When he’s not in the studio, Jackson keeps a busy touring schedule. In 2010, he opened for Bobby Valentino and Lil Wayne, and in 2012 he supported R. Kelly at a concert in Dallas. “I’ve rocked some pretty nice size crowds of 2- to 4,000 at my performances in New York, Los Angeles, Chicago, Iowa, Nebraska, Virginia and many more,” he said.

No matter where the road takes him, Jackson doesn’t forget where he’s from, and is known for his loyalty to those who have supported him from the start.

“I’ve been able the see the whole transition from that first day we were college roommates at Point Park University in Pittsburgh,” said longtime friend Marcus Wright. “He had a basic keyboard and the ability. His sound has really evolved since those earlier days.”

Mary Ann Shaul had been a fan of Jackson’s music for years when she reached out to help raise money for a co-worker’s daughter who needed an organ transplant. Jackson donated the proceeds from his CD sales. “He is just a genuinely super nice guy. He does a lot for a lot of different people—it seems like he is telling his story through his music,” said Shaul, who describes Jackson’s style as “up-to-date, very upbeat, honest and clean.”

The growth of Jackson’s career has enabled him to form business relationships around the country, and he’s working all angles to get his current video “Too Close, Too Personal” (shot locally at The Boneyard restaurant on Market Street) aired through outlets like MTV and BET. “Unfortunately, it takes time, and sometimes the right time to really catch a break,” Jackson said.

Jackson’s songs are born from real life experiences. “Too Close, Too Personal” is about people emerging from your past, reaching out for money, plane tickets and other favors. Jackson said they see you on social media and in Hollywood and “assume that you’re rolling in big money, and not understanding the struggle.”

But, like any rising musician, the biggest challenge is getting, and holding, the attention of a mainstream audience. “Financially, it’s tough,” he said. “I do everything myself…but that’s fun—the real challenge is trying to be heard by the masses.”

There were two pivotal moments in Jackson’s life that solidified his journey to keep moving forward with his music. The first occurred on a train ride while living in Chicago in 1999. “Me and my boy were just rapping, just messing around on the train—when we rap it has to be kind of soulful, it’s not super aggressive and over the top because I want to pull you in, make you listen and feel it,” he said. “We were sitting there rapping doing our thing, I had my hat out and a women put money in my hat. That was, like, a moment when I said, ‘I’m getting paid for this?’”

The second occurred in 2000 when Jackson entered an overnight celebrity contest with 92.7 in Charlottesville. Local artists submitted their songs, which were played on the radio and listeners voted. Jackson was selected as one of the top 10 contestants, and performed at Saxx Jazz Lounge Club (now Monticello Antiques), where he took first place and won $500.

“I was never going to look back anyway,” he said. “But that win solidified it for me.”

Jackson enjoyed a long stretch of exposure after his contest win, and he is determined to rekindle it with the release of Frederick.

“As long as I’m alive, I’ll be doing this,” Jackson said. “Regardless if I’m on R. Kelly status, or I’m right here where I’m right now. I’ll still do it, like every day, because I’m passionate about it, and I love expressing myself creatively.”—Janet Thomson

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