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?”
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 L. Alexander is a Washington Post staff writer. He can be reached at firstname.lastname@example.org.