Celebrity makeup artist Derrick Rutledge ’79 on life’s layers

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Derrick’s 12+3 Tunes that Take Him Back

Primer

Derrick Rutledge ’79 is a work in progress. At 61, with the face and buoyant spirit of a 38-year-old, he’s like a phoenix rising from all the broken bits and anguish of life. 

Derrick was a bullied child, who found refuge at GDS—only to have his musical dreams deferred in college. Instead, he found his calling through the pages of fashion magazines. Barely a few years out of college, he became known as the “big man who could ‘beat face’”—shorthand for applying makeup with breathtaking results.

He gained devoted clientele among the stars, then the superstars. Early 2009 found Derrick splitting his days between the East Wing of the White House with First Lady Michelle Obama; Chicago, South Africa, and Los Angeles with Oprah Winfrey; church on Sundays; and his mother’s Washington, DC bedside as she battled cancer. 

As much as he’s gained in the last two decades, he’s also lost a lot. From just before his 40th birthday until today, he lost both hip bones (since replaced), pieces of his pelvis, and 300 pounds in his lifelong struggle with obesity. He lost his mother to cancer and nearly lost his life, when an 18-wheeler flung his car from the road.

And still, he’s rising. The “Makeup Maestro’s” art now graces countless covers of those same fashion magazines that emancipated him. 

In a 2011 Washington Post article on Derrick, reporter Keith L. Alexander wrote, “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.”

Every Oprah public appearance in the last 12 years, including all her movies, show tapings, and magazine covers, has showcased Derrick’s handiwork. He runs two cosmetic brands—Derrick Rutledge About Face (DRAF) and Perfecting Your Presence (PYP)—works out daily, and works tirelessly to help others achieve the best version of themselves.

“I see my time on this Earth as a healer,” Derrick said.

"I see my time on this Earth as a healer."
 

Foundation 

Derrick always struggled with his weight and his self-esteem, particularly in the face of actual (and perceived) persecution by his peers. In public elementary school, he protected himself by doing their homework and hiding. He was different and smart, teachers said; when his handwriting was recognized on others’ pages one too many times, they urged his family to find a private school.

Derrick attended GDS from 7th grade to graduation and keeps up with friends, including Kamal Ali ’80, Marc Fuller ’79, Thomas Johnson ’79, Ron Lucas ’79, Leroy Nesbitt ’78, and Scott Shepperd ’79, several of whom also sent their own children to GDS.

He remembers close relationships with, among others, Kevin Barr—“Love me some Kevin Barr!”—Harold McNeill—“He was like a big brother to me!”—and Dorothy Jackson—“I’m getting the chills seeing Dorothy’s number is still in my phone!” They stayed in touch regularly until her passing in 2010.

Derrick was an artist and a talented singer at GDS, who performed in all the musicals, seder programs, and Christmas assemblies. “Music has always been in my soul,” he said. Derrick was a superfan of the ‘Godmother of Soul’ herself, Patti LaBelle, who used to pick him out of the crowd at her concerts and invite him onto the stage to sing his heart out on “Lady Marmalade.”  (Several years after a vocal coach at Webster University shut down his dreams of ever being an opera lead because of his big body, he would go on to spend nearly 20 years on tour with LaBelle, not as a singer, but as her makeup artist).

“I ended up really loving GDS,” Derrick said. “I never felt that I fit in, even though I had a good life there. Not to say that people treated me badly but rather because I didn’t feel good about myself. That [feeling] expanded into how I believed people felt about me. I always believed that weight was an issue. Dorothy was a person I could talk to about that. She taught me that I could believe in myself and go after what I really wanted to do.”

"She taught me that I could believe in myself and go after what I really wanted to do.”

 

Concealer 

Fashion and art were his means of escaping. He picked up photography in college, attempting to mimic what he saw in magazines. Later, with a tackle box of cheap wet n wild beauty products, he began to do free makeup for female classmates; and, after college, he continued with the free or $5 makeup audition jobs for producers he met at fashion shows. A few good breaks later, he got a call from Black Entertainment Television (BET) because Miss USA Kenya Moore had requested him for her appearance on the network. He stayed with BET for almost a decade, doing makeup for the hosts and celebrity guests, including a young Beyoncé with Destiny’s Child, Sisters With Voices (SWV), TLC, En Vogue—“all the girl groups from the 90’s”—as well as Lil’ Kim, Aaliyah, and Queen Latifah.

Despite his size, Derrick had a way of positioning himself out of view: hidden in corners to eat alone, watching the stars from offstage, and working behind the makeup chair. Even when his five-foot seven-inch frame at one point carried nearly 600-pounds, with a 72-inch waist, he managed to conceal himself—and his deteriorating physical and mental health—behind the beautiful faces and the work. 

"...he managed to conceal himself—and his deteriorating physical and mental health—behind the beautiful faces and the work."
In 1999, Derrick underwent gastric bypass surgery and began the long journey to health, wellness, and self-esteem. 

Artistry

Highlights

Derrick knows and follows the latest makeup trends but is known for giving timeless looks. You’ve seen his work, even if you didn’t realize it. After hanging up on a White House phone call, thinking it was a prank, Derrick began working with FLOTUS, and it was her TIME magazine cover that caught Winfrey’s eye. His artistry for Winfrey’s turn as Mrs. Which (pictured) in Disney’s 2018 film A Wrinkle in Time is unmatched. 

Shadow, Eyebrows, Lips

Derrick works happily in the shadow of all these stunning Black women, but he’s learned to spread his wings. He’s perfecting his presence and adopting some of his most confidence-boosting techniques on his own face, including his signature arched eyebrows. Makeup with Derrick is joyful work: music is ever-present, whether he’s singing and dancing with his clients, including the former First Lady, or hearing Whitney Houston in his head as he does Ms. Winfrey’s lips, while she reviews a script or reads a book for an author visit. (“You’re the lip master,” she tells him.) Other times, they’ll pop on some Teddy Pendergrass or the Aretha Franklin gospel album, sing, and reminisce. 

He's perfecting his presence.
 

Final Dusting, Set, and Seal 

These days, he’s looking after himself, even while bouncing between time zones, weddings, funerals (including for Ms. Winfrey’s father in July 2022), movies, and magazine shoots. He’s been at this work long enough that those first brides he made up for next to nothing when getting his start are now calling him up to do their daughters’ wedding makeup.  

“He makes every day your prettiest day, and every woman is looking for her prettiest day,” Ms. Winfrey told The Washington Post.

His smile and soft speaking voice radiate warmth. “The makeup person is the last person you see before you go on set, and his energy affects your energy,” Moore said of Derrick for the 2011 Post feature. “He has the most beautiful spirit.”

“There are a lot of layers to me and my life,” Derrick said. “I’m a constant work in progress, always looking to be a better Derrick and help someone along.”

That’s a legacy worth leaving.

“I’m a constant work in progress, always looking to be a better Derrick and help someone along.”
 

To follow more of Derrick’s story, find him on Instagram @derrick4mkup or visit his websites at DRAFonline.com and PerfectingYourPresence.com.