Makeup Maestro Derrick Rutledge has a candid talk with Obvious Magazine’s Beauty Editor about his professional journey, struggle with overweight, and painting face for “The Two Big Os.”

Words by Beauty Editor: Jen Prudhome

Twenty-three years ago, Derrick Rutledge started his career as a makeup artist in college while studying Producing and Directing, in addition to Vocal Performance. A major part of his studies consisted of studying fashion photography and professional lighting, an experience which made him familiar with posing models, and gain an understanding of the best angles for his subject. While staging his own fashion shoots, he became accustomed to painting the faces of his own models.

“That’s why it’s very difficult to for me to be at a shoot and not say something. Because I love to pose models I know how to make you look your best. The face angles and what lighting is best.”
It was this area of his education that allowed him to exercise his artistic abilities which included drawing and painting. His knowledge of color from his art background allows him to understand the importance of color when applying it to the face, as well as the placement of dark and light.

“I come from an old school of artist where they didn’t have money to afford airbrushing to make things perfect, you had to be perfect.”

Once he graduated from Webster University he moved to Washington, DC he met a publisher that asked him to assist on a major photoshoot, which lead to an opportunity for him to go to Europe.  For six weeks Derrick led beauty shoots for several companies and hair salons which opened opportunities for his work to be featured on billboards. When the publisher sold his company to Dudley Products in North Carolina, Derrick was asked to run beauty books for Dudley.

After three years he was asked to develop and expand their product line by adding additional colors that complement an array of skin tones. Derrick considered this to be a major stepping stone for his budding signature collection.

While Derrick did not remain with Dudley Products, his exit opened new opportunities. He received a phone call several months later asking him to work with Black Entertainment Television (BET). They wanted him to work with Kenya Moore, (the key makeup artist at BET went on vacation), and Derrick was asked to extend his services to the flagship shows on the network for over five years.

“What had happened was at that time BET would bring in the [music] artists and they would come in with their makeup artist.  But word started to spread around about this big guy that worked in the makeup room that could paint face.”

His tenure at BET allowed him to work beauty wonders with clients on a consistent basis including Patti LaBelle, Chaka Khan, Yolanda Adams, and Cece Winans. He recognized that his field of work gave him a unique opportunity to help other people but it also opened doors for his own personal development. Derrick’s professional journey also brought him to the core of his weight problems, and in a monumental weight-loss feat, he was able to invest more time into his individual enterprise after his move away from BET that he regards as a leap of faith. He considered overweight as something that did not have to be an obstacle in the midst of what he wanted to achieve. Derrick shared that his spiritual connectedness brought him the honor of working with “the two big Os:” Oprah Winfrey and First Lady Michelle Obama. “I’m truly grateful, truly honored, and truly blessed…”

Jen: Among your clientele you’ve worked with Oscar winning actress Mo’Nique, music legend Patti LaBelle, media mogul Oprah Winfrey, and First Lady of Michelle Obama. What about your work resonates with all of these women?

Derrick: What I do for Oprah, First Lady Michelle, Mo’Nique, Yolanda, CeCe, Chaka, you, your sister, your mother, is give every one of my clients an experience. It’s more than just giving someone good makeup or finding someone that can paint. I’m calm. I’m soothing, and I’m genuine. I look at someone. It’s all in the way that I touch them, the way I apply moisturizer on their face, and look at them in their eyes so they can feel a genuineness coming from me. I’m very passionate when I make someone up. As I’m making them up I’m seeing them transform. It’s not necessarily putting on a lot of makeup; it’s just enhancing what they have. When you look good you feel good.

JP: Everyone was awestruck by Oprah Winfrey’s appearance at the Met Costume Institute Gala, where she was Oscar De La Renta’s muse.

DR: You don’t understand how good it made me feel for her to ask me to do that. You know? I had only worked for her a couple of times and then she asked me to do that. It was such an honor. And it was such a big event. Then there was the photo she took with Lady Gaga that night for Vogue. That was absolutely beautiful.

JP: She looked phenomenal and you could tell that Oprah felt great that evening. For such a major event, where do you start with your inspiration? Do you see the dress or have a conversation with her?

DR: I knew she was going as Oscar de la Renta’s face for the night. Which meant every eye was going to be on her, and him. This was big because it was dealing with the fashion world. They showed me sketches of the dress, and then the actual dress. So I started drawing an eye on a paper, and a lip on another piece of paper so I painted two different types of eyes and lips. I had two or three ideas for what I wanted to do and I when asked her if she had any ideas of what she wanted, she said “just, paint me.” We did her photoshoot the day before the [event] but they made it to look as if it was shoot the same day; which was good because it gave me an opportunity to see what she was going to look like the night of the gala. That preparation comes from the O Magazine covers. My first issue was the July issue of her lying in the hammock, and the infamous one that everyone was raving over was the cover Oprah in the short wig.

JP: When you say transformation, that cover was a transformation.

DR: Yes. And when it comes to Michelle O, people absolutely love the piece of her in black and white with her hands on her face; there was the cover of Glamour from December of last year. We went to Olso, Copenhagen, and the State Ball where the Salahis snuck in. I’ve had so many people say that night was the most beautiful picture she has taken with the President.

JP: I’d love to hear more about DRAF (Derrick Rutledge About Face) and what you are doing for aspiring beauty trailblazers of the future?

DR: I started bringing in makeup artists to shadow me, learn my technique and be able to paint the way I painted with their own touch. I’ve been mentoring young upcoming makeup artists by taking what they’ve already learned and show them what they need to do to become better. The true test is when you have to get out there and do [the work] live. I’m a firm believer that you’re a constant student. As long as I’ve been doing this, I still feel that I can always learn.

To learn more about DRAF (Derrick Rutledge About Face) please visit http://www.drafonline.com.

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  • http://Www.fashionmodelconsultant.com Tondaleya

    Thank you for sharing Derricks story. I had the honor of working with him almost 24 years ago at my very first fashion show at the University of Maryland Eastern Shore. He is an absolutely phenomenal artist and I will never forget the experience of watching him work. I will never forget what he said to me when he completed my makeup, “go head Diana” …referencing my resemblance to Diana Ross. That experience led me to my accomplishments within the industry today.

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