Discovered working in a Miami record store at age 16, singer-songwriter Debbie Deb, née Wesoff-Kowalski, is most famously known for her signature freestyle selections, “Lookout Weekend” and “When I Hear Music.” Today, the ‘80’s legend, who still rocks crowded arenas, also specializes in designing one-of-a-kind works of art and jewelry. Our Debbie Deb interview helps you get to know the Florida native.
The new Kendrick Lamar single, “Squabble Up,” may have reminded fans of her contributions, but she’s been working in the background for the last few decades and still has quite the story to tell.
Parlé Mag: Let’s hop right into this Kendrick Lamar single, “Squabble Up,” which samples your smash hit entry, “When I Hear Music” — How did this opportunity even present itself to you?
Debbie Deb: In this industry, opportunities don’t really present themselves to you; they just show up after the fact.
Parlé Mag: How do you feel about the overall response that his song and sample has been receiving?
Debbie Deb: The reaction has been completely overwhelming for me. My social media is non-stop, and trying to keep up with it has become almost a full-time job. I’m totally not complaining.
Parlé Mag: That said, what have you been up to, both personally and professionally speaking, during your musical hiatus?
Debbie Deb: I’ve been doing shows around the country up until the last few months. I don’t like traveling over the holidays. Plus, my son Elijah just had a baby girl, so I’m busy being a grandma!
Parlé Mag: Reflecting, tell me your whole inception into music — When did you first become interested? And how did it all begin for Debbie Deb?
Debbie Deb: My story is really not a secret. I was in high school and worked in a record shop. I met a big Miami producer, and we got together—his music, my lyrics—and the two entities came together. I wasn’t thinking about contracts to protect me at that time, so things definitely got sour.
Parlé Mag: You’re well traveled. Talk to me about how being from New York influenced you and how that compares to Florida.
Debbie Deb: I am a Miami native; I was only born in New York. My whole life, I’ve lived in South Florida until I moved to Philly in ’99. Now I’m back in Florida. With that being said, I’ve always been influenced by New York rappers in the ’80’s. Miami was a little behind in the early ’80’s with rap, but it definitely turned the tables not long after. My biggest influences in the early ’80’s were: Grandmaster Flash and the Furious Five, Planet Patrol, LL Cool J, Afrika Bambaataa, Run-DMC, and the list goes on.
Parlé Mag: That said, how do you describe the style of music that you created?
Debbie Deb: I was definitely into R&B and old-school rap. Things changed in the ’90’s when rap just became too much. Of course there were amazing artists, but for the most part it kind of turned me off. I got into Reggae and Hard Rock, believe it or not.
Parlé Mag: As a songwriter, when you sit down to pen your lyrics where do you draw inspiration from?
Debbie Deb: Even now, songs just pop into my head. I’ll be driving or in the shower and wish I had a pen and paper. I’m starting now to voice-record things as I think of them, thanks to technology. It’s definitely made things easier.
Parlé Mag: Switching gears here, what exactly do you want people to get from your music?
Debbie Deb: I’m just grateful that the songs I did in the ’80’s have had such an impact in this crazy industry. I never in a million years would have thought they would stand the test of time. It humbles me. I love how creative new artists can be with that old-school influence.
Parlé Mag: If you could collaborate with any one artist, living or dead, who would it be and why?
Debbie Deb: I would, of course, love to work with Kendrick, lol. But I’m very old-skool still, so I would love to work with Missy Elliott, Grandmaster Flash, Sugarhill Gang, to say a few.
Parlé Mag: If you could play any venue in the world, which one would you choose and why?
Debbie Deb: I’m very shy, believe it or not!! I would be nervous at my dream venue, but of course Super Bowl!
Parlé Mag: On a more serious note, are you happy with the current state of music?
Debbie Deb: Technology has really taken over the rawness of that old-school vibe. There are definitely amazing artists, but I still like the rawness of just singing and hearing the original voice of the artist, with just a beat.
Parlé Mag: What do you feel has and will continue to be the key to your longevity?
Debbie Deb: If I knew the answer to that, I’d be a billionaire! The songs I’ve done have taken on their own life. People enjoy them, and they will keep them alive as long as they want to dance!
Parlé Mag: Do you have any additional aspirations, maybe even completely away from music?
Debbie Deb: I’m just living each day the best I can. I enjoy doing art and making different things. I was a hairdresser for 30 years, but have since retired. I still do shows, but I’ve slowed down with that—they really take a lot out of me. I have lupus, so I just try to stay healthy with the beach, sun, and fun.
Parlé Mag: To date, what has been your biggest career moment, at least thus far anyway?
Debbie Deb: There are definitely a few. I was able to go to Iraq and do shows for the troops. That was an amazing experience. Also, a few months ago, I did a huge show at SoFi in L.A. with Lionel Richie and Diana Ross headlining. There were 100,000 people, 5 rotating stages. It was a very insane experience for me. The love was overwhelming.
Parlé Mag: What’s an average day like for you?
Debbie Deb: I live a very slow, easy life. When I’m not in Philly, I try to get to the beach or do something outside. I love the water, so anything with water involved, I’m there! My husband and I live a very drama-free, easy life.
Parlé Mag: Please discuss how you interact with and respond to fans…
Debbie Deb: Everyone I meet, I treat like a friend. I am told I’m too humble, but that’s really all I know how to be.
Parlé Mag: What is your favorite part about this line of work? Your least favorite? And, why?
Debbie Deb: I’m not a fan of the music industry. It can be very shady. I have met a lot of wonderful people during my journey. I enjoy hearing how my songs made an impact on people’s lives. That’s the most gratifying thing for me.
Parlé Mag: What advice would you have for someone wanting to follow in your footsteps?
Debbie Deb: What happened to me happened in a very organic way. I wasn’t prepared. I would say to any artist: just protect yourself and copyright everything.
Parlé Mag: Looking ahead, say five or maybe even ten years from now, where do you see yourself?
Debbie Deb: Hopefully, I’ll stay healthy. Hopefully, I’ll still be rocking crowds and just living my life the best I can.
Parlé Mag: “Lookout Weekend” and “When I Hear Music” are bonafide classics — How did these particular songs come about? Who came up with their concepts? And, please describe for me the overall studio vibe on those fateful days?
Debbie Deb: Those songs were something that wasn’t planned. I was given amazing music by Pretty Tony, and I just wrote amazing, truthful lyrics to them. I was only 17, so the whole experience was exciting for me at that age. But who was thinking about contracts and the impact those songs would have? I sure wasn’t. I paid a big price. Along the years, I’ve been able to get my story out, and that’s been very gratifying for me.
Parlé Mag: As for the immediate, what’s next for Debbie Deb?
Debbie Deb: I never know what’s around the corner for me. I never know who will call me. What is meant to happen will happen, when it is meant to.
Parlé Mag: Is there anything I left out or just plain forgot to mention?
Debbie Deb: Well, I think you really covered a lot of questions people may be wondering. I’m always grateful to tell my story.
Parlé Mag: Lastly, any “parting” words for our readers?
Debbie Deb: I always say keep things real and keep it old school. With those two things, you can’t go wrong. I’m thankful for all the love I’ve been given. The beginning of my career was pretty rough, but karma always prevails!
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