Cynthia Bailey Unapologetically Enters Her Third Act At An Age-Defying 56 Years Old

by | Sep 10, 2023

Gold pleated strapless dress with origami folds: SemSem  Gold chandelier earrings with quartz stone: Sheila B. Jewelry  Shoes: Sergio Rossi

American model, TV personality and actress, Cynthia Bailey, is entering her third act in life with no desire to settle into an agist cliché. The third act of any great movie is often seen as one of the most important elements of the story. The pre-climax resides in the resolution of the main character’s decisions, having previously overcome immense obstacles. At 56-years-old, Bailey is age-defying the preconception that life impedes but instead she is undertaking her third act with finesse.

Gold pleated strapless dress with origami folds: SemSem  Gold chandelier earrings with quartz stone: Sheila B. Jewelry  Shoes: Sergio Rossi

“This part of my life is called my turn,” says Bailey. Arising from humble beginnings in Alabama, Bailey has been navigating the entertainment industry since she was eighteen years old. She was discovered by the Wilhelmina modeling agency and broke barriers in the modeling industry strutting cat walks in Milan and Paris. In 2010, she was asked to join season three of the Real Housewives of Atlanta. Eleven drama-filled seasons later, Bailey gracefully walked away a household name. Reflecting on her many milestones, Bailey sits down with Mr. Warburton Magazine’s, Editor-and-Chief, Derek Warburton to talk about embracing aging, owning your destiny and why now more than ever, her third act is her most important role to date.

Pontell Diamanté Cape Sleeve Gown: Tadashi

MR. W: You started from humble beginnings and beat the odds sky-rocketing to a successful career that was unfamiliar to a girl from Alabama. How has your background shaped you?

BAILEY: I have always been a dreamer. I didn’t rise out of darkness, per se but I have experienced a lot of peaks and valleys to get to where I am today and it feels amazing. Even at 56 years old, I am still living my dream. Re- creating and reinventing myself three times in my life. There was Cynthia the model, Cynthia the TV personality, and now it is Cynthia the actress. This is honestly the third act of my life. I believe in my heart, and I believe in God, and I believe that the best is yet to come. I’m just getting started.

MR. W: Personally, we have been friends for years. I always refer to you as the beloved Cynthia Bailey. Because of your success and your platform, do you feel people look up to you as a beloved persona?

BAILEY: First of all, Derek, I love that word. I have been called many things, but beloved isn’t one of them. I think it is a powerful way to express how you see me and how you feel others see me. I do feel that someone, like myself, who comes from such humble beginnings to rise to this level in my career is motivational, an inspiration.
I don’t want to give the impression that I don’t doubt or question the things I’m doing in my life. At the end of the day, what I love and what I strive to do is to stay the course. To continue to pray and manifest the things that I truly want and work hard to get them and be consistent.

Green/Bronze sequin maxi dress with ruffles: OTT Gema drop earrings: Swarovski Shoes: Sergio Rossi

MR. W: What advice would you give to someone living or pursuing a dream that would help them navigate this new world?
BAILEY: Find a group of like-minded people that love and support you. I think about my friendship with you, Derek. You are a part of my village. There are days where I don’t wake up feeling inspired. However, with you, and other like-minded people in my village, who are also driven and focused on making their dreams come true, will motivate me. I get inspired from the people that I surround myself around.I wish that when I was younger, I knew the importance of the company you keep. We need that honesty, we need true love, and true fellowship from the people that actually care about us.MR. W: What is the biggest misconception when it comes to wealth?
: Wealth is not money. Wealth is peace. Wealth is love. Wealth is health. I don’t want to be the only one in my villagewinning and everyone around me is struggling or has nothing. I think the true wealth is when everybody is winning.

Purple top and pleated skirt: Alice and Olivia  Magenta floral headband by: Julia Clancey  Shoes: Donna Karan

MR. W: Now, let’s talk about acting! This isn’t technically a new industry for you. You’ve been acting since 1985. Your first movie was The Dark Power. In 1990, you were in an episode of The Cosby Show. From the film, For The Love of Money to The Five Heartbeats, what aspect of acting is different for you this time?


BAILEY: I never thought I would really be on TV. When it started happening, I remembered, I wanted this, I prayed for this. Recently, I recall saying, I’m going to transition from being a TV personality to an actress. I had to sign up for classes and focus. This is not an easy industry to get into. I knew coming into the game I wanted to be taken seriously, which is why I never made acting a side job. Hence why I didn’t pursue it while I was modeling or on The Real Housewives of Atlanta. I don’t want to be an okay actress. I want to be an actress; I want to be able to tell incredible stories through my acting.MR. W: What secrets do you have for people who are coming of age? In view of the fact that you are at an age when so many women feel like it is over for them?BAILEY: I’m single again at fifty-six. Professionally, I walked away from an incredibly high paying job to pretty much start at ground zero as an actress. In the beginning those eggs do not come in as an actor, honey!
The audacity to really live in my purpose. The audacity to live the life that I want to live. I can’t worry about how it is going to happen, but just live in my truth, live in my faith and know it is going to happen.

Hite wool crepe suit blazer, long sleeve and white crepe pants: Rebecca Crews Necktie: Charles & Ron Shoes: Gianvitto Rossi

“I wanted to show Cynthia in a different way. No wigs, just character.” – Derek Warburton

MR. W: Recently, you moved back to Atlanta from Los Angeles. The headlines are reporting that you are in this happy, sad state about your divorce. Are you in fact, happy and sad?

BAILEY: I am happy and sad in a way. I am sad that my marriage did not work out but I am happy that my ex and I moved on. We both have an opportunity to now find our person.

MR. W: What advice would you give to women starting over?

BAILEY: The advice that I would give to my sisters of a certain age is, you are the only person that can control your life. How you want your life to go. Manifesting the things that you want to happen. Doing the work to put things in place that you want to happen. We forget that we have control.
No one controls my life except me and God, that is it. I would also say, trust yourself. One of the conscious decisions I made for 2023 was to start trusting myself more. To stop second guessing, stop living in a place of fear. Trust yourself, trust your gut. Your intuition is powerful.

Orange coat: Adiba Gold interlinked hoops with pearl seashells earrings: Sheila B. Jewelry Butterfly brooches: Julia Clancey Shoes: Missoni

MR. W: Most people don’t know that you are a Grade A mother. A single mother, who not did not lose herself while rising to stardom. Often women spend their entire life giving to everyone else, motherhood, and forgetting to take care of themselves. How do you feel about the concept that so many women feel they are finished in your age group?

BAILEY: Thank you so much Derek. Regardless of the projects or businesses I operate, Noelle has always been my number one priority. When I found out I was pregnant, I knew my life was going to change. Prior to that, I was doing everything for myself. I just wanted to travel, afford nice things and live the life that I want to live. However, once I became a mom, everything changed! Immediately everything I did; I did for us.

Don’t get me wrong, Leon is amazing. He’s an incredible father, he’s a very honorable person. With that said, I actually became stronger and more ambitious as a Mom, than I ever was on my own. I used that energy to fuel my passions.

MR. W: Can we just say, you are drop dead gorgeous! You are happy. Your jobs are done. Your family is well and taken care of. What does this third act look like to you?

BAILEY: This part of my life is called my turn. My daughter is grown. My Mom is well. I can focus on my passions full time. You will see me traveling a lot more. I was recently in London; I went to Mick Jagger’s 80th birthday party and it was wondrous. These are the types of things that I want to do now with my life. It is my life and I want to enjoy it. This next chapter for me, is thriving professionally as an actor, but also thriving, as a person.

“I have been friends with Cynthia half of my life and this is the first time she has posed for one of my magazines. I feel the world has a specific view of her but I see so much more. She is a chameleon & at 56 years old Hollywood isn’t gonna know what hit them when she gets the right role.” Derek Warburton

Fuschia Solid Maxi Dress: OTT Shoes: Gianvito Rossi

Watch full interview:

Production Credits:
Creative director: Derek Warburton
Photography: Rowan Daly
Article: Ashley Foster
Makeup: Garret Gervais
Hair: Jason Tavares
Wardrobe stylist and images edited by: Keiki Tomoyose