The Washington Post

Makeup artist Derrick Rutledge makes over Michelle Obama, Oprah — and himself

NEW ORLEANS — Chaka Khan is more than angry.

Instead of getting to rest before her show at the Louisiana Superdome, the R&B star has been booked for two speaking engagements. She’s holed up in her hotel suite, fuming. Outside, her assistants are waiting for her to open the door.

Her makeup artist, Derrick Rutledge, is waiting, too. He just flew in to do her after working on Michelle Obama in the East Wing. After New Orleans, he’s scheduled to fly out to do Oprah Winfrey before returning home to Washington.

But first Rutledge has to persuade Khan to open the door. Finally, after 15 minutes, she does, and Rutledge distracts her by talking about two of her favorite subjects: tennis and shopping.

Within 30 minutes, Khan emerges, reddish mane flowing, lips sensuous in burgundy, looking glorious in a lace dress and carrying a hand fan.

“It wasn’t a good day,” Khan later admits. “I was nervous about speaking, but he calms me. He knows what to say to me.”

Rutledge has worked for Khan for 15 years. He knows what his client and close friend needs: a hug and some orange juice. “I’m more than just makeup,” he says. “I’m there for support as well.”

Rutledge is the man behind the look of some of the world’s most famous names. A leading makeup artist, he gets as much as $15,000 for a day’s work and boasts a coveted client list, including two of the nation’s most photographed faces, Michelle Obama and Oprah, as well as singers such as Patti LaBelle, Shirley Caesar and CeCe Winans. Just last month, his work was on the covers of Essence and AARP, which featured Obama, and O, which featured, obviously, Oprah.

A makeup artist does intimate work. More intimate than a hairdresser or personal assistant. Like an artist caressing a canvas, Rutledge touches and transforms faces, erasing flaws and reshaping contours. He brings out beauty, confidence, the sheen of stardom.

At a little after 9 p.m., with the audience roaring, Chaka Khan takes the Superdome stage. She’s a vision of wild beauty. Her boundless alto soars across the adoring, raving fans.

From backstage, Rutledge watches her on a monitor. “Yessss. Work, Chaka,” he cheers.

Had life dealt him a different set of cards, he’d be up there maybe, or on some stage, delivering arias as an opera star. They said he had the voice, he just didn’t have the beauty. He has battled obesity all his life — at his heaviest, his 5-foot-7-inch frame carried 565 pounds, with a 72-inch waist. At 50, he sometimes walks with a cane, or two, the result of mangled bones and cartilage from a lifetime of excessive pounds. That weight has defined his destiny.

Rutledge escapes pain by creating beauty. Life in his makeup chair is flawless. There’s no ugly here. No teasing.

* * *

In a fashion studio tucked away in a meatpacking district of Chelsea in New York, Rutledge is working on Winfrey as the media mogul prepares to shoot covers for her O magazine. Winfrey has used Rutledge since she saw the first lady on the June 1, 2009, cover of Time. “I said to myself, ‘Who did that?’ ” Winfrey recalls.

At the time, Winfrey and her makeup artist, Reggie Wells, had “parted company” after 10 years, and she was auditioning new artists. One took two and a half hours — “I swear I wanted to cry,” Winfrey says, sitting in the makeup chair wearing a white robe and slippers as Rutledge applies her lipstick. One candidate told her he had the wrong foundation, but if he had had the correct makeup, she would have looked great. Another put so much makeup on her face that she said she looked like a carny.

She had met Rutledge when he had accompanied LaBelle to her talk show. But there was an unspoken rule among the divas: “You don’t mess with other people’s people,” Winfrey says. “I thought Derrick belonged to Patti.”

When she heard Rutledge was doing others, Winfrey snatched him up. “The first lady comes first. When she doesn’t need him, I get second dibs,” Winfrey says.

Winfrey never sits still in the chair. Rutledge moves with her as she bends, talks, laughs. He’ll stop, inhale deeply and continue. Also challenging: If Winfrey has eaten the wrong thing (salt) or has been traveling, her face will be bloated or worn. “I just sit in this chair and watch Derrick do his reconstructive surgery with the brushes, and I get my face back,” she says.

The right makeup is critical for these women. It “immediately creates a level of assurance,” Winfrey says.

Winfrey and best pal Gayle King, standing a few feet away, begin to squabble over who has the best description of Rutledge’s work. King, also a client, agrees with O editor Susan Casey, who says Rutledge “brings out the glow” of every woman. But Winfrey has the final say: “He makes every day your prettiest day, and every woman is looking for her prettiest day.”

Today is one of Winfrey’s prettiest days as she is escorted onto the set wearing the long red dress and steps in front of the cameras. Cue wind machine and lights. Lady Gaga is pumping through a nearby laptop, and Winfrey begins posing, left, right, hair toss, flash of the famous smile.

Today is also a good day for Rutledge. He’s stronger and is able to limp slowly on his own, without his canes. As he so often does during these moments, Rutledge stands off to the side in his black smock, cheering on his latest creation. “Werrrk. Yes. Fieeeerce,” Rutledge says as he pats his hand on his thigh to the music. “I still can’t believe I’m here sometimes,” he whispers.

* * *

Derrick was always oversize, says his mother, Regina, sitting at the dining-room table in her Northeast Washington home, which is adorned with photos of her son with famous clients. She holds a 1962 clipping from the Afro-American newspaper about Derrick winning a baby contest. In the photo, he’s wearing a bow tie, vest and shorts. The caption reads: “Ever see such a fat young fellow!”

As a toddler, Derrick wore extra-large clothes. By the time he was in third grade, he weighed more than 100 pounds.

Regina Rutledge is a caramel-skinned woman with silver-curled hair, a broad smile and little makeup. She looks like a 1950s actress who could have co-starred in Dorothy Dandridge films. Makeup was never her thing, she says. She never had time for such, trying to rear six children with her husband, William, who worked in the records section at the U.S. Office of Personnel Management. She was a teacher, then principal at Drew Elementary.

Regina, 78, pauses to apologize to visitors for being weak; she is undergoing chemotherapy in her second bout with cancer in two years. William died three years ago at 80.

All her children were “stout,” Regina says, but Derrick was the biggest. She’d fix healthful meals of vegetables, but the kids would cook what they wanted when their parents were at work, or they’d eat fast food. “I told them they were digging their own graves,” she says.

School became place of brutal teasing for Derrick. Bathroom breaks and recess were the worst, he says. Every time the shy, overweight child went to the bathroom, boys would bully him. Once, several trapped him there and beat, kicked and urinated on him, leaving him on the floor as they went back to class. “I took a lot,” he says softly. “It’s too painful. I’d rather leave it in the past. I always end up crying.”

His younger siblings often had to fight for him — Derrick didn’t fight. He wasn’t like other kids. He didn’t play outside. He never learned to ride a bike or swim. He preferred to stay in the house, thumbing through fashion magazines or listening to classical music, recalls his brother William Jr. Derrick took refuge in his church choir — and food. Food, while a big source of his pain, was also a source of his comfort.

Derrick finally devised a way to get his classmates to stop bullying him. He agreed to do their homework. But the teachers noticed his handwriting on his classmates’ assignments. They told Regina Rutledge that it might be better if Derrick attended a private school to get away from the neighborhood children. The Rutledges enrolled him in Georgetown Day School.

In the 1970s, tuition was about $3,000 a year, a bit much for the Rutledges, who also sent Derrick’s youngest sister, Regina Ruth, accepted on an academic scholarship. The remaining four children, their mother says, “wouldn’t have been able to cope” at the private school with predominantly white classmates.

To pay for her son’s tuition, Regina Rutledge catered on the weekends, with her six children helping to cook.

Each weekday morning, the family would climb into Regina’s station wagon, and she would drive across town to drop off William at work, then the kids at school, then herself at her school. Every morning, they drove past 1600 Pennsylvania Ave.

“I never dreamed that one day he’d be there, in the first lady’s living quarters, in her makeup room. Her children call him Mr. Derrick,” Regina says smiling. “I am just so sorry my husband was not able to see this. ...

* * *

Rutledge thrived at diverse Georgetown Day. He joined the school choir and theater. The family often went to watch him in student musicals such as “Guys and Dolls” and “My Fair Lady.”

In art class, colors fascinated him, how they blended. While other children drew houses and cars, Rutledge sketched almond-shaped female faces, recalls his childhood friend, Ronald Lucas, 50, now a public relations executive in New Jersey.

Rutledge got a music and academic scholarship to Webster University in St. Louis. His strong, lyric tenor made him a natural for opera. On stage, Rutledge felt in control. Audience members may have snickered when, at 400 pounds, he’d slowly make his way to the microphone, but by the time he was done singing, “I had won them over, and they’d be standing to their feet applauding.”

He had found his life’s calling. He dreamed of being center stage, under the bright spotlights, emoting Italian arias. The Metropolitan Opera or Carnegie Hall became his goal. He envisioned his family sitting in the audience, bursting with pride as his voice crescendoed to a high C.

But his voice teacher — overweight himself — told Rutledge that his bulk would never allow him a successful career as an opera lead, reserved for muscular, handsome tenors. His future would be relegated to lower paying, chorus stints. “He said no one wanted to hear a nice voice on a big body,” Rutledge recalled. “I was devastated.”

He changed his major to media studies and focused instead on a career behind the scenes of the entertainment world. He took up writing, studio production and photography.

When he’d take pictures of women, he’d ask to do their makeup. His subjects would hand him their lipstick and compacts, then be impressed. He learned how artificial lights affect colors, both the makeup’s and the skin’s undertones.

Rutledge returned to Washington after graduating in 1984 and began doing makeup for whomever would allow him, mostly brides, models and drag queens. He’d volunteer to gain experience or charge $25. He got jobs at makeup counters at the Hecht’s and Woodward & Lothrop department stores, and checked out every library book on makeup he could find.

Next, he took a job as a makeup artist for then local fashion photographer Gary Lyons. Lyons had little patience. He’d walk over to each model Rutledge had made up and hold up a magnifying glass to show him the flaws. “I would be on the brink of tears, but it taught me perfection,” Rutledge says.

Rutledge also freelanced for fashion and hair shows. He befriended an unknown Baltimore comedian and model named Mo’Nique, and a Howard University freshman named Malaak Compton, who later married comedian Chris Rock (she hired Rutledge for the wedding; then Rock used him when he taped his 2004 HBO special at Constitution Hall). In 1987, Compton was a regular in Howard’s elaborate fashion shows. “With some artists, you get up feeling you’re wearing a mask,” she says. “But with Derrick, even back then, I always felt naturally beautiful. His gift is very, very rare.”

* * *

It was not until 1993 that Rutledge finally made it into the entertainment world, albeit through the makeup room.

BET hired Miss USA Kenya Moore as a guest host for its “Video Soul” program. Moore, a former model who had worked with Rutledge before, agreed to host if the TV network brought him in to do her makeup. “I needed to feel good. The makeup person is the last person you see before you go on set, and his energy affects your energy,” Moore says. “He has the most beautiful spirit, and he wasn’t a diva.”

BET executives were so impressed with Rutledge that they kept him. Eventually, he was doing the makeup for hosts of all of the network’s programs and guest stars, including a teenage Beyoncé Knowles and Destiny’s Child.

Rutledge earned $250 a day and worked from 8 a.m. until 11 p.m. He rarely left the makeup room. He had ballooned to more than a quarter of a ton, and the room was his oasis from co-workers he thought snickered or frowned in disgust at him.

Like many overweight people, he refused to eat in public. He would bring his food from home and eat between seeing clients, never venturing into the cafeteria. He didn’t want people to notice him. “I’d go into a room and push myself into a corner and have a seat,” he says. “I had a way of disappearing, even at 600 pounds.”

To those around him, Rutledge just looked like a workaholic. “He was always there, like a lamp,” jokes former “Video Soul” co-host Donnie Simpson.

Simpson says he never truly appreciated Rutledge’s talent until he appeared on another TV station and was made up by that show’s artist. After the show aired, his friends and family called asking if he was okay. “I looked dead,” Simpson recalls. “If I was in a cemetery, a corpse would turn over and say, ‘You look really pale.’ ”

During the next decade or so at BET, Rutledge built a loyal following among celebrities. He was quick, thanks to his ability to use both hands to paint, earning him a reputation as a makeup artist “who could ‘beat face,’ ” he says.

It could be trying work. One rapper berated him so badly, he rushed out to his car and sobbed. A soul diva took one look into the mirror, stalked into the bathroom and stripped off the makeup, demanding that he redo it. The scene played out three times. After the third, the diva yelled so loudly her manager burst in to see what was the matter. Her manager later apologized to Rutledge, saying the singer was angry because her regular makeup artist failed to appear and the piano she was to play was out of tune. BET ended up canceling the singer’s appearance.

For most artists, the more Rutledge painted, the more they wanted him — for videos, album covers, tours.

“Derrick loves arching the eyebrow and making the eyes alluring and inviting. You can tell Derrick’s work anywhere,” explains gospel singer Yolanda Adams, sitting in a Baltimore photo studio recently as Rutledge paints her face for a fashion shoot. The two have worked together for 18 years, since Adams’s early appearances on BET.

Derrick’s magic rested beyond his brushes and powders, in his demeanor. The man who was often hurt by others’ words used his own words to make people feel confident.

“There’s a maternal side that lets you know, no matter what you are going through, when you sit down in his chair and that brother starts touching you, everything is going to be all right,” Mo’Nique says.

A year after Rutledge started at BET, LaBelle came to Washington to perform at President Clinton’s birthday celebration. At that time, LaBelle did her own makeup. But when she arrived, she discovered that her Louis Vuitton bags with her makeup and gowns were missing. She panicked.

“Honey, they stole my drag,” LaBelle recalls.

The celebration organizers quickly contacted BET, which sent over Rutledge.

LaBelle had known of Rutledge for more than a decade — but as a die-hard, screaming fan who’d follow her from concert to concert. It was part of her show to call on members of the audience to join her on stage to sing along on “Lady Marmalade,” and whenever she’d see him, wearing his bright colors, she’d pick him. LaBelle remembers how it took four security guards and stage hands to “roll his big behind” onto the stage. When he made it up there, he’d grab the mike and take over the spotlight. He’d belt out those operatic notes, effortlessly dancing like a man half — actually three-quarters — his size and steal the show, she says.

So when BET sent him to her, “my fat baby Derrick comes to the door, and I’m like, ‘Thing, you can’t do my makeup,’ ” she says. “ ‘You’re a singer, not a makeup artist.’ ”

But Rutledge won her over. He eventually left BET and went on tour with her. “Baby, he can make a monkey look like a queen,” LaBelle says.

For more than 15 years, Rutledge traveled the world with LaBelle. It was a glittering life, but inside he was growing more miserable.

* * *

Rutledge’s self-esteem and body were crumbling as his weight ballooned. He became depressed. When he drove, he had to recline his seat all the way back because his stomach hit the steering wheel. When he caught flights, he would board last to see if there were open seats together where he could sit with a seat-belt extension. And when he went to a movie theater, he would go to the last row and sit on the chair’s armrest, because he couldn’t fit in the seats.

He’d try dieting but end up bingeing more. His friends constantly warned that he wouldn’t live to see his 40th birthday. Sadly, many of these same friends never reached their own milestone birthdays. Some died from cancer, others from complications of AIDS. Life was short, he realized, and he wasn’t enjoying it.

In 1999, in preparation for his 40th birthday and with financial help from Adams and Khan, Rutledge paid $38,000 for gastric bypass surgery. His insurance wouldn’t pay because he refused to undergo six months of psychological evaluations before the surgery. “I didn’t have time for that,” he says.

During the first six months after the surgery, he shed about 200 pounds. Ironically, his body began falling apart. The doctors told him his bone structure, while damaged by the weight, had been insulated by the fat. When he began losing, the insulation was removed, unveiling the years of damage to his body.

He had both hips replaced. The cartiledge in his right knee eroded, and his right leg became nearly two inches shorter than his left. He had two vertebrae repaired. He carried 50 pounds of excess skin around his stomach and chest like drooping, brown sandbags, sending sharp pain through his back. He had to start wearing girdles and tightening garments.

At one point, Rutledge became more depressed at how his body looked after the surgery than before. “All the happiness went to unhappy again,” he says. “I looked worse, because all the skin was hanging.”

Then in 2006 while preparing for a concert in Alabama, pain began shooting through his body from his legs. He never told anyone, instead finishing the tour’s final two cities.

Doctors later told him his left pelvis had crumbled and was held together only by muscle. The damage left him in the hospital for five weeks.

* * *

In March 2009, Rutledge’s phone started ringing repeatedly, but he didn’t recognize the number and didn’t answer. When he finally did, the caller said it was one of Michelle Obama’s assistants and asked if he wanted to audition to be her makeup artist.

“I thought I was being punked,” he says. But Rutledge’s name had been floated to White House officials after Obama’s Chicago artist got tired of commuting to Washington.

Rutledge was summoned to the White House to prepare Obama for a St. Patrick’s Day dinner. He chose two foundations, one to highlight and another to even her skin tone. And he focused on her eyes. “She has the most incredible eyes, and people notice them immediately,” he says.

Two years later, Rutledge is Obama’s main makeup artist. His schedule is as grueling as that of any White House official in top health. Most recently, he flew to South Africa with Winfrey in her private jet, then to Chicago, then to Los Angeles. When the White House summons, he flies back to Washington, even for a day or two, as he did to prepare the first lady recently for promotional videos and the Congressional Black Caucus dinner.

With the demands of Obama and Winfrey, he has been forced to cut back many of his former clients, including LaBelle. (Mo’Nique did fly him out to Los Angeles last year to do her makeup for the Oscars when she won best supporting actress for “Precious.”)

He hasn’t had a vacation in years, because when one client is vacationing, another needs him. And he has set up a company of artists, photographers and hairstylists he can dispatch when he can’t go himself. It’s called DRAF (Derrick Rutledge About Face).

He and his business manager-housemate, Tim Byrd, are creating a line of makeup and hair-care products under the brand Ü Lifestyle. “What he has, is come up with a formula for brown girls,” Winfrey says. “Estée Lauder, are you listening?”

Today, Rutledge says he’s happier than he has ever been. He’s half his original size, down to 265 pounds and a 44-inch waist, the smallest he has been since junior high school. He has had the excess skin removed, and his goal is to weigh less than 200 pounds.

On the road, he spends at least 3o minutes a day in hotel gyms. At his four-bedroom split-level in upper Northwest Washington — where he and Byrd live with his three cats, Mascara, Shadow and Powder — he brings in a personal trainer each day for hour-long workouts. Now that his stomach is smaller, he consumes diet shakes, cottage cheese, vegetables and pieces of meat, between fat-burning pills. He meditates and prays.

He regrets not being more active when he was a child. He remembers what the first lady tells him about working out: “You’re not doing this for now, but for 10 years from now.”

His confidence has blossomed and revealed his own diva-like qualities. Each morning, he applies a light foundation to add color to his face. His eyebrows are neatly arched. He shadows his beard to hide the gray. And when he travels, even if for only a week, he carries three large suitcases, one just for his shoes. “Every outfit has to have its own pair of shoes,” he says.

With change comes a new outlook on life. He hopes his new body will lead to love, possibly even his first relationship. “I was always told I had a cute face but that I would be even better looking if I lost the weight,” he said. “But that just forced me further in a shell. People thought they were being nice, but it hurt.”

While his transformation is astounding, Rutledge continues to struggle with his physical ailments and additional sagging skin that makes up much of the remaining 100 or so pounds he still wants to lose.

In New Orleans, Khan’s entourage darted across the mammoth convention center, whisking her to her next speaking engagement. Rutledge, with his two canes, trailed behind. By the time he caught up, the entourage had already squeezed onto a freight elevator.

“What about Derrick?” someone called out. “We’re leaving Derrick.”

“He can catch the next one,” snapped Khan’s guard. The elevator doors shut with Rutledge standing on the other side.

Once again, his body was an obstacle. “I knew they were trying to get there quick,” Rutledge says. “I don’t take it personally.”

So, as he has done since his childhood, he used the episode to fuel a transformation.

“I feel very good about myself now,” he says, with determination. “And I plan to look as good as I feel. Yessss.”

Keith Alexander covers crime, specifically D.C. Superior Court cases for The Washington Post. He has covered dozens of crime stories from Banita Jacks, the Washington woman charged with killing her four daughters, to the murder trial of slain federal intern Chandra Levy.
Show Comments
Most Read



Success! Check your inbox for details.

See all newsletters

Close video player
Now Playing

To keep reading, please enter your email address.

You’ll also receive from The Washington Post:
  • A free 6-week digital subscription
  • Our daily newsletter in your inbox

Please enter a valid email address

I have read and agree to the Terms of Service and Privacy Policy.

Please indicate agreement.

Thank you.

Check your inbox. We’ve sent an email explaining how to set up an account and activate your free digital subscription.