Cynthia Bailey on Modeling, Entrepreneurship and the ‘Real Housewife’ Life - OZY | A Modern Media Company

Cynthia Bailey on Modeling, Entrepreneurship and the ‘Real Housewife’ Life

Cynthia Bailey on Modeling, Entrepreneurship and the ‘Real Housewife’ Life

By Nick Fouriezos


Because she rose from small-town Alabama to big-city stardom while staying true to herself.

By Nick Fouriezos

Model, actress and reality TV star Cynthia Bailey sat for a revealing interview with OZY’s CEO and co-founder on the latest episode of The Carlos Watson Show. The following are some of the best cuts from the full conversation, which you can find on the show’s podcast feed.

On her origins

Cynthia Bailey: I’m originally from Alabama. I grew up in a small town called Tuscumbia. Tuscumbia, Alabama, which is only famous for being the birthplace of Hellen Keller, and now Cynthia Bailey from Housewives of Atlanta.

Small-town girl. I left Alabama when I was right out of high school, and I moved to New York City to pursue my modeling career, and I thought I would maybe be in New York like a year. I didn’t even know there was a fashion industry when I moved to New York. I just was really like a country girl that got presented an opportunity and I was like, “OK, Mom, Dad, I’m going to go and see what happens, and I’ll probably be back home and start college in a year,” and never looked back. 

Carlos Watson: Did you always have that feeling and that affirmation that you were attractive?

Bailey: You know what? I felt like I was a cute girl. I felt like I had it going on, but I didn’t feel like I was a model. No one ever said, “Oh, my God, you’re so beautiful. You’re so striking. Your cheekbones.” Models are a different kind of beauty. The standards for what is a successful model, just in terms of beauty standards, is a little different from the girl next door who’s gorgeous, and beautiful, and all the guys like. I was definitely tall and skinny and had the high cheekbones. I mean, I looked like an ostrich. You know what I’m saying?

So, with that said, there’s a lot of guys at my high school that probably have a lot of regrets right now that they didn’t ask me out, because now they have to see me on TV all the time. They’re like, “Damn, I should’ve asked her out when I had the chance.” I was definitely a late bloomer. … But still, I never thought, “Oh, I’m so gorgeous. I should pursue a modeling career.” I never knew I had what it took. I didn’t even know what it took to be a model until I was approached by a modeling agent.

On her big break

Bailey: This is what happened. I was homecoming queen of my high school. I was actually the first African American homecoming queen of my high school. I went to a predominantly white high school in Alabama and I was the first Black homecoming queen. I was invited to participate in a homecoming queen pageant, which was in Atlanta. I remember driving to Atlanta and I couldn’t even afford a dress for the pageant, so I just wore the same homecoming queen dress that my mom had bought me.

I participated in the pageant. First and only pageant I’ve ever been in and I didn’t win, I didn’t place. Not even Miss Congeniality. Nothing. Like nothing, but as it turns out, I did kind of win because I was the only one that was approached by a model scout who happened to be one of the judges in the pageant. … I was still kind of salty I didn’t place in the pageant. I was like, “Wait, I don’t even know what that’s all about, the modeling thing.” I didn’t know.

We grew up kind of poor. We didn’t have magazines and stuff. I could get my hands on an occasional Ebony, or a Jet, or an Essence or whatever, but I was pretty excited that this little white lady from Wilhelmina Models in New York City — her name was Betsy. I’ll never forget her — approached me and was like, “Hey, you ever thought about moving to New York City and becoming a model?” That was like speaking Swahili to me. I live in Alabama. I just happened to be in Atlanta at the pageant. I never thought about getting on a — I had never even flown on an airplane.

So, it was crazy, but she gave me her card, and this is before cellphones. I am a woman of a certain age, so no cellphones. And I remember taking her card and telling my mom. I was like, “Hey, this white lady said that she thinks I could be a model, and she lives in New York. She was saying maybe I could move to New York,” and of course my mom was like, “Girl, you ain’t going nowhere right now. You just finished high school.”

But once that seed was planted, I just never forgot it. I was like, “Wait a minute. I’m already kind of making history. I’m the first Black homecoming queen of my high school. Maybe God really has more stuff for me to do.” So, I worked on my parents for probably another six months and convinced them to let me go to New York to try to pursue my modeling career, which that one action pretty much changed the whole course of my life.

On being a reality TV star

Bailey: A whole world opened up. I was like, “Wow, OK, so this is like a big deal being a reality star,” because at that time, Carlos, a lot of people looked down on reality stars. A lot of my friends who actually are on reality shows themselves now, at the time I was like, “Hey, they keep asking me about this show, this reality Real Housewives. What do you guys think?” And they’re like, “Oh no. You have such a great reputation. You have a such a great whatever. You don’t want to go on that show. You don’t want to go on reality TV. It’s going to destroy everything that you worked so hard for.”

So, basically everyone told me not to do it, and for some reason, little Miss Cynthia, who just always goes with her heart and gut, something said, “Do it. Let’s see what happens. And if I don’t like it, then I don’t have to do it anymore.” My whole life is like, “Oh, I’ll just go to New York, and if it doesn’t work out, I’ll just go back to Alabama. All right, I’ll just go on TV for a year. If I don’t like it, I could always quit.” But it always ends up being my destiny, and journey, and story. It’s so crazy. 

I am definitely different, but in a good way. I’m stronger. I’m way more fearless. I’ve been able to do things that I never thought I would do. Being on the show kind of pushed me. Now that I was in the spotlight I was like, “OK, well, now that I got everyone’s attention, I got to really make the world proud and do something.” So I started all my businesses on the show. Honestly my first business was the Bailey Agency School of Fashion. If I wasn’t on the show, I don’t know if I would’ve pushed myself so quickly to start a business, because I kept saying, “I got to make this make sense. If I’m going to be on a show like this, I want to show entrepreneurship. I want to show me being a mom. I want to show all these different things.”

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