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Jessie Woo Is A Multihyphenate Force To Be Reckoned With

The Haitian seeester-in-chief is taking things up a notch as a triple threat.

BOSS UP

As we all know, the entertainment industry is a beast—especially for women of color. From television to music, it is fairly (or unfairly) understood that black women are often portrayed as aggressive, argumentative, or hyper-sexualized. Even for those of us who choose to celebrate their crowns through basic talent and hard work, the journey of "making it" comes with a unexpirable set of challenges.

And most frustrating of all, for those ladies who have a heavier dosage of melanin—such as the Justine Skyes or Normanis of the culture—that journey becomes that much more of a challenge, regardless of how talented they are. With knowing this, we have become highly aware of the fact that the resiliency to conquer this beast of an industry, must always, and only, be unwavered.

But what's a beast to a beast?

Someone who can explain entirely is Jessica Juste, the triple-threat, Haitian seeester-in-chief, who has affectionately captured our hearts, televisions, and social media scroll. We know her best as Jessie Woo: host, stand-up comedian, and ultra-talented vocalist, who has encapsulated her brand geniusly.

And with the recent release of her charting debut EP, Moods of a Cancer, Jessie Woo is proving her beast to be solid.

Ten-toes down, solid.

Courtesy of Jessie Woo

We sit down to discuss her evolution into music and womanhood since her last chat with us; and getting to know Jessie was admittedly a joy. She reminds me of a butterfly that is shy because it's blossoming from its caterpillar state, but also knows her new wings are poppin' as they emerge.

During our conversation, I study her presence. Her aura has a majestic possessiveness for her character and space, and she carries an unexpectedly stoic demeanor. She's fun but reserved and I am immediately enamored with the code switch from 'professional' to 'vibrant social media personality.'

I take note of her skilled approach, and ask how it feels to emerge from a class of fellow highly sought-after black women (Luvvie, Jackie Aina, Chrissle, etc.) with large platforms that the culture often looks to for their views on relevant topics. "I just keep it real," she says. "I'm not always joking, things aren't always funny. I've used my platform to speak on alot of things; politics, sexual abuse, Haiti, makeup, relationships. I think people gravitate towards folks who are honest; folks who aren't afraid to be transparent."

She's been a bit busy with being a host for various largely embraced platforms (Will Packer's Power Star Live, stages at Essence Fest, BETher red carpets, etc.) and managing a social media account of hilarious content that garners millions of views from her loyal 630K+ followers. And now, Jessie has slowly transitioned to a place she has always felt she should be, since she was a young girl: music.

With a standout single (and my jam) "Vacation" on the airwaves, and an EP peaking at number two on the R&B iTunes charts, Jessie is finally receiving well-deserved recognition for her music. "I was so scared to release this EP. Like, even the night before I asked myself, 'Are you sure you want to do this?' But I did. I wasn't going to let anything hold me back. So, we released it the next day and it beat Chris Brown, girl! I have the screenshot!" she says with a laugh.

"An evolution is happening for sure, in a great way. [Now] when people see me out and about, they talk about my music first."

Known as a boisterous ambassador for her ancestry of Haitian descent, she proudly flies the flag of her heritage through her music, comedy, and vibrant personality. "I grew up going [to Haiti] all the time. It's my favorite place to vacation. My mom is from Gonaïves (up north) and my dad is from Jeremie (down south). Unfortunately, people focus on the bad, the ghettos of Haiti, the political turmoil. Haiti has its issues just like every other island and every other black country in the world, but don't count us out. We've given too much to humanity to be cast aside."

Footage of boat rides on the clear waters, meetings with senators and tourism boards, and her roaming through the streets of Cap-Haïtien fill her instagram on her recent trip for a music video.

"Going back to Haiti to shoot the video for 'Vacation' was so important," she says. "It is very important to me that I use my platform to educate people about the Wakanda of the Carribean. It is beautiful. The beaches are unlike anything you are ever going to see. The food is incredible. The people are amazing."

I quickly realize that you can literally hear her smile and admiration of Haiti each time we discuss it.

"And 'Vacation' is the most popular song on the EP for obvious reasons. It's flavorful R&B, EDM and kompa all in one, so it all just made sense."

I take a moment to brag on her vocals and then I ask how she manages to balance the pressures of being a comedian, with wanting to be taken seriously as an artist. "You know what, that's a good question. I was just speaking with my manager, Shaft, about that. He worked with Cardi B on 'Bodak Yellow' and that's who he compared me to career-wise. I look to her as someone who has mastered the balance of the two beautifully. She is silly when she wants to be, but she is also serious when it's time to be serious. And whether you like her or not, one thing she is always serious about, is her music. And I feel we have that in common."

Another factor the two have in common is a stint in reality television. She speaks briefly on what she has learned through the process and if she would change anything. "Definitely. I wasn't prepared and I didn't know the politics behind it. I made mistakes in front of millions of people but God still had favor over me. What was meant to destroy me, turned out to be for my good."

I couldn't agree more.

"But I think my resume pre-reality TV, helped prevent reality TV from defining me. I hosted Essence Center Stage at Essence Fest this year. That was major. That opportunity didn't come from reality television. That came from Essence seeing my BET Breaks work, my BETher red carpet work, my Power Star Live work. Thank goodness I laid a solid foundation down so that opportunities could still roll in because chile," she laughs. "God is good!"

Courtesy of Jessie Woo

With her plate full and cup running over, I can't help but wonder how she manages to decompress and practice self-care. And although she hasn't quite figured out a routine yet (send her some tips, yall!), she does enjoy being in the quiet at home, which gives her the opportunity to think, talk to God, and process her feelings.

To keep her mental health in check, she does credit friends like Tanya Hoffler (BET producer), Jamila Mustafa (MTV's TRL), and Yves Carmelle (music agent at ICM) as women that she can look to for advice in navigating this chaotic industry. "[Yves] was one of the first people to reach out to me when folks started spreading my funny videos online. She's a successful Haitian woman who is well-respected and it means a lot to me to have access to her."

We close out with me asking her to describe herself. And without hesitation, she says, "Jessie Woo is a Haitian woman who loves God, has a great education and is talented beyond measure. She's not afraid to be herself, and make mistakes while reaching for every star destined to hang in her sky. She's a fearless go-getter, who is going to leave a major mark on this world."

I smile and think to myself: Wi, seeester.You already have.

For more of Jessie, follow her on Instagram @thejessiewoo.Moods of a Cancer is out now.

Featured image courtesy of Jessie Woo.

You may not know her by Elisabeth Ovesen – writer and host of the love, sex and relationships advice podcast Asking for a Friend. But you definitely know her other alter ego, Karrine Steffans, the New York Times best-selling author who lit up the literary and entertainment world when she released what she called a “tell some” memoir, Confessions of a Video Vixen.

Her 2005 barn-burning book gave an inside look at the seemingly glamorous world of being a video vixen in the ‘90s and early 2000s, and exposed the industry’s culture of abuse, intimidation, and misogyny years before the Me Too Movement hit the mainstream. Her follow-up books, The Vixen Diaries (2007) and The Vixen Manual: How To Find, Seduce And Keep The Man You Want (2009) all topped the New York Times best-seller list. After a long social media break, she's back. xoNecole caught up with Ovesen about the impact of her groundbreaking book, what life is like for her now, and why she was never “before her time”– everyone else was just late to the revolution.

xoNecole: Tell me about your new podcast Asking for a Friend with Elisabeth Ovesen and how that came about.

Elisabeth Ovesen: I have a friend who is over [at Blavity] and he just asked me if I wanted to do something with him. And that's just kinda how it happened. It wasn't like some big master plan. Somebody over there was like, “Hey, we need content. We want to do this podcast. Can you do it?” And I was like, “Sure.” And that's that. That was around the holidays and so we started working on it.

xoNecole: Your life and work seem incredibly different from when you first broke out on the scene. Can you talk a bit about the change in your career and how your life is now?

EO: Not that different. I mean my life is very different, of course, but my work isn't really that different. My life is different, of course, because I'm 43. My career started when I was in my 20s, so we're looking at almost 20 years since the beginning of my career. So, naturally life has changed a lot since then.

I don’t think my career has changed a whole lot – not as far as my writing is concerned, and my stream of consciousness with my writing, and my concerns and the subject matter hasn’t changed much. I've always written about interpersonal relationships, sexual shame, male ego fragility, respectability politics – things like that. I always put myself in the center of that to make those points, which I think were greatly missed when I first started writing. I think that society has changed quite a bit. People are more aware. People tell me a lot that I have always been “before my time.” I was writing about things before other people were talking about that; I was concerned about things before my generation seemed to be concerned about things. I wasn't “before my time.” I think it just seems that way to people who are late to the revolution, you know what I mean?

I retired from publishing in 2015, which was always the plan to do 10 years and retire. I was retired from my pen name and just from the business in general in 2015, I could focus on my business, my education and other things, my family. I came back to writing in 2020 over at Medium. The same friend that got me into the podcast, actually as the vice president of content over at Medium and was like, “Hey, we need some content.” I guess I’m his go-to content creator.

xoNecole: Can you expound on why you went back to your birth name versus your stage name?

EO: No, it was nothing to expound upon. I mean, writers have pen names. That’s like asking Diddy, why did he go by Sean? I didn't go back. I've always used that. Nobody was paying attention. I've never not been myself. Karrine Steffans wrote a certain kind of book for a certain kind of audience. She was invented for the urban audience, particularly. She was never meant to live more than 10 years. I have other pen names as well. I write under several names. So, the other ones are just nobody's business right now. Different pen names write different things. And Elisabeth isn’t my real name either. So you'll never know who I really am and you’ll never know what my real name is, because part of being a writer is, for me at least, keeping some sort of anonymity. Anything I do in entertainment is going to amass quite a bit because who I am as a person in my private life isn't the same a lot of times as who I am publicly.

xoNecole: I want to go back to when you published Confessions of a Video Vixen. We are now in this time where people are reevaluating how the media mistreated women in the spotlight in the 2000s, namely women like Britney Spears. So I’d be interested to hear how you feel about that period of your life and how you were treated by the media?

EO: What I said earlier. I think that much of society has evolved quite a bit. When you look back at that time, it was actually shocking how old-fashioned the thinking still was. How women were still treated and how they're still treated now. I mean, it hasn't changed completely. I think that especially for the audience, I think it was shocking for them to see a woman – a woman of color – not be sexually ashamed.

I hate being like other people. I don't want to do what anyone else is doing. I can't conform. I will not conform. I think in 2005 when Confessions was published, that attitude, especially about sex, was very upsetting. Number one, it was upsetting to the men, especially within urban and hip-hop culture, which is built on misogyny and thrives off of it to this day. And the women who protect these men, I think, you know, addressing a demographic that is rooted in trauma that is rooted in sexual shame, trauma, slavery of all kinds, including slavery of the mind – I think it triggered a lot of people to see a Black woman be free in this way.

I think it said a lot about the people who were upset by it. And then there were some in “crossover media,” a lot of white folks were upset too, not gonna lie. But to see it from Black women – Tyra Banks was really upset [when she interviewed me about Confessions in 2005]. Oprah wasn't mad [when she interviewed me]. As long as Oprah wasn’t mad, I was good. I didn't care what anybody else had to say. Oprah was amazing. So, watching Black women defend men, and Black women who had a platform, defend the sexual blackmailing of men: “If you don't do this with me, you won't get this job”; “If you don't do this in my trailer, you're going to have to leave the set”– these are things that I dealt with.

I just happened to be the kind of woman who, because I was a single mother raising my child all by myself and never got any help at all – which I still don't. Like, I'm 24 in college – not a cheap college either – one of the best colleges in the country, and I'm still taking care of him all by myself as a 21-year-old, 20-year-old, young, single mother with no family and no support – I wasn’t about to say no to something that could help me feed my son for a month or two or three.

xoNecole: We are in this post-Me Too climate where women in Hollywood have come forward to talk about the powerful men who have abused them. In the music industry in particular, it seems nearly impossible for any substantive change or movement to take place within music. It's only now after three decades of allegations that R. Kelly has finally been convicted and other men like Russell Simmons continue to roam free despite the multiple allegations against him. Why do you think it's hard for the music industry to face its reckoning?

EO: That's not the music industry, that's urban music. That’s just Black folks who make music and nobody cares about that. That's the thing; nobody cares...Nobody cares. It's not the music industry. It's just an "urban" thing. And when I say "urban," I say that in quotations. Literally, it’s a Black thing, where nobody gives a shit what Black people do to Black people. And Russell didn't go on unchecked, he just had enough money to keep it quiet. But you know, anytime you're dealing with Black women being disrespected, especially by Black men, nobody gives a shit.

And Black people don't police themselves so it doesn't matter. Why should anybody care? And Black women don't care. They'll buy an R. Kelly album right now. They’ll stream that shit right now. They don’t care. So, nobody cares. Nobody cares. And if you're not going to police yourself, then nobody's ever going to care.

xoNecole: Do you have any regrets about anything you wrote or perhaps something you may have omitted?

EO: Absolutely not. No. There's nothing that I wish I would've gone back and said to myself, no. I don’t think at 20-something years old, I'm supposed to understand every little thing. I don't think the 20-something-year-old woman is supposed to understand the world and know exactly what she's doing. I think that one of my biggest regrets, which isn't my regret, but a regret, is that I didn't have better parents. Because a 20-something only knows what she knows based on what she’s seen and what she’s been taught and what she’s told. I had shitty parents and a horrible family. Just terrible. These people had no business having children. None of them. And a lot of our families are like that. And we may pass down those familial curses.

*This interview has been edited and condensed

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Feature image courtesy of Elisabeth Ovesen

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