South Florida Rapper Jessy Taylor Gives HHW an Exclusive Interview as You’ve Never Seen Her Before

HHW Staff
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Read Time:13 Minute, 16 Second

Interview By Kim Coco

Introduce yourself to our readers! Let them know your name, where you’re from & what we all know you for!

My Name is Jessy Taylor and I’m from Clearwater, Florida- born and raised. Most of you would know me as a viral influencer and Internet comedian. You may also recognize me from being on TV. But more importantly I’m an artist. I’m a rapper.

Jessy Taylor, you’re not just an artist- you’re actually an amazing rapper! Over the past few months you have quietly been putting in the work behind the scenes on a project and you’re about to give Hip Hop Weekly the exclusive. Tell the readers what you’ve been working on all this time!

Since 2017 I have been working on my passion- which is my music. I’m a female rap artist. I started on Sound Cloud as a rapper. Some older people that have seen me in the media and not keep up with me may see me as this viral sensation and stop short there. I have been working so hard in the studio more than usual. I’m now ready to take over the female rap game.

Jessy – On Sept 18, 2020 you officially dropped your newest single. I heard it and its dope by the way. Drop the name of that project so our readers can download it and check it out!

On Sept 18, 2020, I officially released my single entitled – Lifestyle. It’s available every now on all platforms so go check it out!


When did you start making music? Did someone or something inspire you to start in the first place?

Music has been and still is everything to me. I started rapping and making music in 8th grade. My passion for music really sparked around 13 years old when I was started riding the bus to and from school and during my walk home. That’s when I really started to get into music. I listened to Drake, Nicki Minaj and Honey Cocaine the most. I really fell in love with making music because it had been something in my life that allowed me to express myself creatively. Look – I don’t write love songs and I don’t share my emotions easily. I have never been that type of girl.

You say you don’t write love songs. Do you think the fans will ever get to hear that side of you?

NO! (Laughs) I’m not that type of person! I’m not trying to make music that is going to make people sad and depressed. I’m trying to bring the energy and get people lit. I like making fun music. I want to lift people up.

You often say you are misunderstood. What do you think the readers and fans would be surprised to know about you?

People know that I grew up pretty wealthy but what they don’t know is that I worked starting at the age of 13 years old. I worked for everything I have. I went to NY and NJ every year because that’s where my father and his family are from. That the reason why I started making more of the East Coast , New York type of hip hop music as opposed to South Florida type hip hop. That’s probably why people tell me I have this Northern accent. I worked at Captains Pizza in Clearwater Beach doing 6 hour shifts during the summer and school year on the weekends. While Surf Style I did 3-12 hour shifts at any given time. I would ride my Razor scooter to get to work because I wasn’t old enough to drive. By the time I was 18 I saved up enough money to get my own apartment .I even went to jail at one point when I was 19 where I was facing 20 years in prison. I’m not ashamed of my story nor do I try to hide it. I worked REALLY hard to get to where I am now. I am so grateful and don’t take it any of it for granted. There’s this saying “A minor setback for a major comeback”

Jessy Taylor through it all you have remained focused and your fans have stayed true. They never left your side. Why do you think your fans love you so much?

Let me say this, I love my fans because they have been so loyal to me. I have a cult fanbase. I am not on the top of the Soundcloud or Spotify charts or being pushed by a record label. People fuck with me regardless and that makes those executives so mad. (laughs) I do everything by myself and still getting more results than people that are signed to record labels who they dropped millions of dollars on. The type of views I get on Instagram I guarantee some of these artist bigger than me can’t get without a “push”. Impossible. I love everyone who is reading either if they fuck with me or not. There is the type of supporter who says they don’t fuck with me in front of their friends than bump my music on the low. My fans love how real and open I am and I expose the truth and the industry. I am who I say I am. I’m not going to change. I can also make people laugh and to me it’s easy to get reactions out of people. I think that a lot of my fans can also relate to me because people look at me and are like – Wait? She worked at McDonald’s? She worked at Wendy’s? And now she is in this position because she never gave up? Well yeah- it’s because I believed in myself when no one else did. The people who said I wasn’t shit, I’m bigger than them. I have always said don’t be a “Why her “ type of person be a “if she can do it so can I “ type of person.

Jessy Taylor – Do you think that being an honor roll student is part of the reason you write so well?

Well ok let’s backtrack (laughs). I had gotten honor roll in 2 semesters and I do have an I.Q. of 138 which is 2 points shy from a genius. If I had applied myself I could have been an honor student but I didn’t apply myself because I never cared about school. I would take a blanket on the school bus and sleep during first period. But yes I think the reason I write so well is because I am intelligent. What’s crazy is people don’t actually know how smart I really am. I just didn’t ever care because I was too focused on working after school and making money. I realized I wanted to go to college around junior year and turn my life around so and that’s why I applied to colleges and I even went to Mississippi State for a semester. Having a criminal record really held me back.

Why do you think that so many people don’t know you are a rapper?

Well for years I have been trying to get myself and my music out there. Every time I went on TV and talked about my music – the media always referred to me as a viral influencer. I would talk about my music but they just didn’t show it. Even on Dr. Phil, they cut out the part of me talking about my music and my passion for it. When I did interviews the media would pick and choose what they felt would sell. The media created this image that I’m an entitled brat and a goodie too shoes but I don’t know any goodie too shoes facing 20 years in prison. The media likes me better as the villain and a dummy. That’s what they think sells. But over time I did start doing music interviews even interviewing up at NYCs Hot 97. I wanted to be taken more seriously with my music and so I even removed almost every video on my YouTube Channel that was not related to my music.

Jessy, Sept 30 2020 you premiered the music video to your latest single Lifestyle. In the video you’re with a few of your girls having fun and the lyrics to that song – you’re saying that this is who you are. This lifestyle isn’t something fake. Tell the readers about the video and the concept behind it.

Growing up I got everything I wanted and I am so thankful for my parents for giving me a lavish lifestyle. Because of being spoiled as adult I have kept up that lifestyle. There was a point where my parents had divorced and my mom I had to start over. Both of my parents are very hard workers and neither went to college, No rich parents, nothing. My dad dropped out when he was 13. My mother graduated high school. They never pushed College as something that you need to succeed. Currently my mother- Sahar Andolino- has become one of the most successful and powerful female real estate agents in South Florida. Both my parents were very hard on me growing up. My father, he has always encouraged me and supported what I do in my career and in my personal life. My grandma also plays a big role in my life also because she was the one giving me a place to stay when my parents kicked me out after I went to jail. My grandmother made sure for two years I wasn’t sleeping in the streets. In middle and high school when people told me that they didn’t work I looked at them like they were lazy. Those same people haven’t done shit with their life with or without a degree. I worked for every single thing I had and the concept for this video is me telling and showing the world that is lifestyle is regular for me because I worked for it. All of this is real. It’s an actual lifestyle that I earned on my own. That’s why I don’t flex my lifestyle because I don’t want to get robbed and killed either. I buy a lot of things that you don’t see on social media. Why does it matter what car I drive or what type of watch I wear? I’m human just like you.

Music Video:

Is your social media personality an alter ego?

I never realized that until recently but yeah it is. One of my friends recently said that to me and I have to agree. He said “Jessica Andolino and Jessy Taylor are 2 totally different people”. I think being Jessy Taylor is my way of protecting Jessica Andolino’s heart. Jessica Andolino is super chill and laid back. She never wears wigs or make up, and is always writing music, working in the studio and having fun. Jessica Andolino is private whereas Jessy Taylor is more open. Jessy Taylor is like this big glamourous personality with the best jewelry, the best designer clothes, beautiful make -up and hair all time being chased by paparazzi hanging out with the biggest rappers in the world. She is loud and exciting and always up for a good time. She’s more of an industry glam girl with the best of everything.

You have a song out with- Solider Kidd. Plug the name of that song so our readers can check that out too!

Yes the song I did with Solider Kidd is called

“By Myself”

You don’t just write and rap. You also engineer your own music.

Yes when I started going to the studio and making music I realized I wanted to learn to engineer. So about 10 months ago I started a music program for a full month and linked with engineer/ producer. I learned a lot from that program. After the third day I was completely on my own. The reason I wanted to engineer is because I wanted to have full creative control of myself and my sound. I know exactly what I want to sound like so it was important for me to do that. I feel really blessed to have been given that opportunity and to have been a part of that program in Pompano Beach. I can probably run a whole studio by myself.

Jessy Taylor, you also have done a lot of charity work but no one talks about that. What causes have you been a part of and what do you hope to be a part of in the future?

When I was in LA I took a trip and visited Skidrow I handed out food to the homeless. Even here in Clearwater I prepared bags of food and handed them out. I’ve done it also in Texas, Louisiana and New York. My goal is to feed the homeless with every chance I get. I give out food to anyone who is in need. I noticed that there are a lot of older and disabled people who are homeless so I especially like giving to them because you know, being in that position and maybe not having any family or any opportunity is what holds them back. That’s my choice though and I do those things from my heart and feel that I have been so lucky that I want to return my good karma. I don’t judge anyone if they chose to do those kinds of things or not.

Jessy- Rapid Trivia – One word answers and no elaborating. Ready?

I’m ready!

How many tattoos do you have?

Oh wow. I don’t even know. Let me count them. 28? Maybe 25? NO! 22.

(Starts counting)

I have Exactly 26 tattoos! ( laughs )

Who are your TOP 5 Rappers of All Time Dead or Alive?

1. Nicky Minaj

2. Honey Cocaine- she really inspired me

3. Lil Wayne

4. Future

5. Young Ma

Sum the current state of Hip Hop in just 1 word


Favorite Old School Female Rapper:

Trina- she’s from South Florida too

Favorite New School Female Rapper:

Young Ma & Nicki Minaj

You’re standing in front of 2 doors. The door to the left goes to your Past and the door to the Right goes to your Future. You get 24 hours behind one of those doors. Which door are you opening?

I would go back to my past because I already know what I’m doing with my future.

Who do you think are the best talent to come out of Florida?

My amazing friend Kid trunks, Lil pump somebody I don’t know personally but admire musically, xxxtention RIP, Smoke Purpp after all he’s also from South Florida and I respect him as a musician.

Speaking of Smoke Purpp, you guys made headlines recently.

Yeah we did make headlines at one point – he has done a lot with his career and although we didn’t end off on the greatest of terms I still & always respect him & wish him continued success.

Jessy Taylor – your HIGHLY ANTICIPATED single Lifestyle is out now! Where can our readers find you on social media? Plug yourself in so we know how to find you for features, collaborations, bookings, business inquiries and more interviews


Instagram: @GGBjessy and @jessytaylorduh

Twitter: @FuccJessyTaylor

TikTok: @JessyTaylorDuh

Press /Media and Bookings:

YouTube: @JessicaAndolini

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