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Secrets of Oprah’s Makeup Artist
Written by Liberty Craig   

The list of famous women whose faces he has blessed with his gift is long. It includes Patti LaBelle, Chaka Khan and Mo’Nique, and it culminates with the two most powerful, most recognizable women in America: Oprah Winfrey and Michelle Obama. Derrick Rutledge is arguably the most sought-after makeup artist in America. At 50, you might say he’s made it. He’s risen far beyond his humble beginnings and fulfilled the American dream of exceeding everyone’s expectations. He’s overcome adversity, lost most of the 600 pounds that restricted both his health and his career, and landed on two feet squarely in the First Lady’s private quarters, or, depending on the day, Oprah Winfrey’s dressing room. Rumour has it that he earns up to $15,000 a day for his work. That’s not a typo.

But this soft-spoken, grounded gentleman is far from the diva one might expect in his role. Derrick’s gentle nature, his innate understanding of people, and his ability to keep a secret are paramount to his success. Of course, his skill with a makeup brush ain’t bad, either. “He makes every day your prettiest day, and every woman is looking for her prettiest day,” Oprah Winfrey told the Washington Post. For Oprah, there’s only one small drawback: “The first lady comes first. When she doesn’t need him, I get second dibs.”

Fresh Vancouver was thrilled to have the opportunity to chat with the fabulous Derrick Rutledge, and to get an inside look at his relationships with these amazing women and his world-class makeup secrets.

Fresh Vancouver (FV): Let’s start by talking about how on Earth you came to be Oprah Winfrey’s official makeup artist!

Derrick: I was doing makeup for Michelle Obama, and Oprah saw the June 2009 Time Magazine cover with the First Lady. At Time Magazine, they don’t like to do touch-ups; they want people to look exactly like they actually look. It was such a close-up of the First Lady and everyone saw how she had been transformed. Oprah said that it was absolutely beautiful – she loved the eyebrows; she loved how clean it looked, how it was very defined and polished.

Oprah thought, whoever is doing the First Lady’s makeup, I’d love to have them do my makeup. She brought me to New York and auditioned me, and after that she started pulling me in to do her makeup for more and more events. Then, she told the First Lady that she wanted to share. Michelle Obama would always have first dibs, but Oprah wanted me to give her that same beauty.

FV: Ever since you came into the picture, Oprah looks more gorgeous than ever. Can you let us in on some of your keys secrets?

Derrick: I appreciate that – thank you so much. I didn’t think people would notice anything, but you’re not the only person who has been telling me that. It’s all due to a makeup line that I’ve been working on for the past eight years that I will be rolling out very soon, called Ooh. Because it’s mineral-based, it looks very natural and doesn’t look like you’re wearing a lot of makeup, yet it gives good coverage.

FV: Oprah is naturally beautiful and has amazing skin, but she has an enormously stressful life and must show signs of fatigue from time to time. How do you make women’s skin look so radiant when they’re struggling with stress and lack of sleep?

Derrick: It’s about having good products and good application. One thing about my clients is that because they have such stressful lives and such long hours of work, they do show signs of stress. But as long as you have a good concealer and good foundation, you can camouflage those signs of stress and no one will ever know. I have one of the best concealers, and one thing I like about it is the fact that it’s waterproof. So you can perspire, cry, be on stage, roll around... it’s not going to run!

The key is to find a foundation that closely matches your skin tone. The mistake that most women make is finding a colour that matches their arm. Your body is always a little darker than your face. Find at least two different shades of foundation. One should be a little darker than the other, because your skin gets a little darker in the summer months and lighter in the winter months. Blend them when you need to. You need two good foundations to achieve the look you’re trying to achieve. You also need a concealer that has a bit of yellow in it, because yellow makes the skin look healthier. A concealer with a yellow base is great for all skin types to camouflage the bluish-grey under your eyes.

FV: Both Oprah and Michelle Obama have gorgeous eyes. What’s the best way to bring out these beautiful features?

Derrick: Start out with a good brow. I approach each face like a picture frame, and the eyebrows are the top of the picture frame. They should be identical twins, not kissing cousins. For many people, one side of the face can be different from the other side, so you want to make sure the brows are even. Good mascara and a good liner will bring the eyes out. From there, coordinate the colour of eye shadow to what the person is wearing and whether it’s a day look or an evening look. I use eye shadows ranging from blues to greens to purples to browns, depending on the event. For a day look, I use more natural colours and for evening, more sultry and jewel-toned colours.

FV: You are known for having not only the magic makeup touch, but a unique ability to personally connect with your clients. Where does this talent come from?

Derrick: It’s been with me all my life. I love people, and my love of people comes through my personality, my touch and my presence. People can feel me as well as I can feel them. I can feel if they’ve had a stressful day and they need a hug or someone to listen to a problem. I’m always that shoulder they can lay their head on. They can also be assured that it stays with me; it doesn’t go anywhere else. That’s why I’ve been able to remain in this business as long as I have, working with high-profile people: they’ve never had anybody come back to them saying they’ve heard any of their secrets or personal information revealed.

FV: People around the world would jump at the opportunity to spend just five minutes with Oprah Winfrey or Michelle Obama. After all that time in your makeup chair, what kind of relationship do you have with these highly respected and adored women?

Derrick: One thing about Oprah is that she is a wonderful teacher. Just like I can feel people, she can feel people as well. She can feel when you’re going through something and you need a shoulder to lean on. Oprah is like a sister. She is a wonderful personality, and a good role model as far as hard work, determination and dedication. The First Lady is also a role model. She is a mother first, who takes good care of her children and instills family values. She is also dedicated to helping other people, which is why she ran her campaign to help with childhood obesity. She knew that I came from that situation and encouraged me to continue on my road. Same thing with Oprah.

FV: Can you tell us more about your personal struggles with obesity?

Derrick: We have to be honest: I work in a profession where people base your worth on your looks. I work in the beauty business. Once I lost the weight, I started hearing from people that they hadn’t wanted to hire me for certain jobs because they didn’t want to book two or three seats on the plane, or they thought I would have a heart attack or just wouldn’t be physically able. It’s a continuous journey because from carrying the weight for so long, I’d done a lot of damage to my bones, which is something I’m working on now. I would never let those issues stop me from doing my job. I don’t want my clients to think I can’t do it, so I push through the pain. I lost the weight because I wanted to be healthier, because I’m in the beauty industry, and because I wanted to live longer. And let’s be honest again: I plan on taking the Ooh Lifestyle System to places unknown and I want to be able to show people that my products instill health both on the body and in the body. I have to be a product of what I’m selling.

FV: Tell us more about the Ooh Lifestyle System...

Derrick: I’m rolling out the hair product line first in Canada, which will be followed by my skincare line, then my makeup products. When I first started out in this industry, I was doing makeup and hair because you have to be able to do both in order to get the job. At some point, I had to choose which direction I wanted to go. But I never forgot about hair care, and I also realized that hair is an extension of the skin. Healthy hair; healthy skin. Anything that goes on your hair goes into your system and comes out on your face. I look at the hair just like I look at the skin, so the products have similar bases. The hair care products are organic and also contain glycolic acid, which helps to cleanse the hair and prepare it for the nutrients in the styling products that nourish the hair.

FV: Your life has transformed even more dramatically than the faces you transform so beautifully. What is life like for you now?

Derrick: People tell me, I want to be like you, I want to do what you do. What they don’t understand is that when I came to this profession, I wasn’t trying to work for famous people. I did it because I love what I do. I love makeup, I love hearing women say how much they love the way they look, and the joy I see on their faces when the makeup is done. But I never get caught up in “me.” That’s the important thing. I never put me in the picture; it’s always the other person. And because of that, big doors have been opening up for me.

Liberty Craig - Editor

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