Remembering Kiki Shepard, one of Black America’s favorite aunties

As with any story about legendary television personality Kiki Shepard, who died March 16 at the age of 74, it starts with the Apollo Theater.

In late 1991, three individuals appeared onstage at the Harlem Mecca to compete in the storied amateur night competition at the venue for a taping of the popular, long-running syndicated television series Showtime at the Apollo.

Billing themselves as the “Unknown Rappers,” the trio, allegedly hailing from Beaumont, Texas, wore brown paper bags with question marks over their heads. Host and comedian Mark Curry looked on, comically perplexed.

“The bags is our gimmick,” one of the men nervously said.

Before they could finish their verse, they were booed by the infamous Apollo audience. Suddenly, the curtain rises, and the bagged group is revealed to be none other than funk-hip-hop act Digital Underground, launching into its gold hit single “Kiss You Back,” led by the late producer, keyboardist and “Humpty Hump” mastermind Shock G.

Cue pandemonium.

“We chose the wackest beat that we could think of to make sure that we got booed,” Digital Underground founding member Ronald “Money-B” Brooks told Andscape. “To pull it off, only one or two of the producers knew what we were going to do. It was a total shock.”

For Money-B and the Oakland, California-based Digital Underground, which also included future music and film icon Tupac Shakur, appearing at the Apollo was the ultimate badge of honor.

It’s a sentiment shared by countless performers who have played the career-launching, 112-year-old Harlem landmark — from Billie Holiday and James Brown to JAŸ-Z. Yet crossing paths with Shepard, Showtime’s larger-than-life co-host, was just as surreal.

“When you think of Kiki Shepard, you think of elegance,” Money-B said. “She always looked great, always looked poised. I can’t even explain the aura that she had, meeting her in person. But you felt like if you were around Ms. Shepard, you had to be on point. You did not want to let her down.”

“It was wonderful to go to work,” Shepard recalled of her 16 years anchoring the NAACP Image Award-winning series in a 2021 interview with The San Diego Voice & Viewpoint. “The United States of America on Friday and Saturday night … people went out, but they came home in time to watch Showtime at the Apollo. We were the talk just like Saturday Night Live was at work the next week. We became a part of that discussion.”

Indeed, even at a time when Black faces were gradually becoming the norm throughout mainstream television in the late 1980s and ‘90s — The Today Show’s Bryant Gumbel, Oprah Winfrey, The Cosby Show, A Different World, In Living Color, The Fresh Prince of Bel-Air, Martin, Living Single, ESPN host Stuart Scott — Shepard stood out, as a TV host, dancer, Broadway performer and actor.

In addition to starting off as the choreographer for Showtime at the Apollo’s dance troupe, she entered the pop culture consciousness as the arbiter of Amateur Night greatness (trust us, if you were a novice performer, you would rather see the inviting face of Ms. Shepard than ageless Apollo legend Howard “Sandman” Sims coming out to literally dance you off the stage) and a legit fashion starlet.

Shepard became so well known for her style prowess and regal wardrobe that rapper Redman, OutKast’s Big Boi, and Kanye West each immortalized her in classic songs. Yet with Shepard, her appeal went beyond the surface. She was Black America’s favorite glamorous auntie.

“I’m not saying this to pump myself up, pat myself on the back or any of that,” Shepard said, “but there are certain elements that made Showtime at the Apollo the success that it was, and when they took away those elements, none of the remakes they attempted could duplicate what we had.”

During Showtime’s star-studded 22-season run, the list of headlining artists was dizzying — LL Cool J, Natalie Cole, Salt-N-Pepa, Keith Sweat, Mary J. Blige, Snoop Dogg, Living Colour, The Notorious B.I.G., Master P, Juvenile, Kirk Franklin, Beyoncé and Destiny’s Child, and more — and there were myriad hosts, with the likes of Sinbad, the aforementioned Curry, Mo’Nique, and most notably Steve Harvey all taking on emceeing duties.

But one constant remained: Shepard.

“Kiki Shepard was absolutely one of a kind,” Harvey wrote on Instagram in one of many heartfelt tributes from family, friends, colleagues and fans celebrating the life of the Apollo fixture. “She was one of the first people to help me navigate this TV business. The kindest person I’ve ever met … Kiki was such a major part of Showtime at the Apollo and was there for the launch of so many great careers in the entertainment industry! Rest in peace my friend.”

Shepard, a Texas native and graduate of Howard University known for her advocacy work raising awareness of sickle cell disease, began her entertainment career appearing in Broadway productions of Bubbling Brown Sugar, Reggae, and Porgy and Bess. Shepard also hit the big screen in the 1978 film adaptation of the Tony-winning musical The Wiz. She made the jump to scripted TV, appearing in such shows as Baywatch, A Different World, NYPD Blue, Thunder in Paradise, Grey’s Anatomy and the 2025 series Highly Favored.

But it was former Apollo owner and Showtime executive producer Percy Sutton who recruited Shepard to be the avatar for what would become one of TV’s longest-running syndicated variety programs.

“It was amazing …,” Shepard recalled to WJBF in 2025 of her early days on the series. “As I said before, Percy Sutton was the top dog of all of it, and Percy made sure that I maintained that job because after the first year, you know, it was an excellent job to have and so many people wanted it. … People were calling every day asking to audition, but Percy Sutton said, ‘No, as long as Kiki Shepard wants this job, she will keep it, because she shows other little Black girls all around the country what they can be.’ And he appreciated the fact that I did it in a very classy manner.”

During nearly every Showtime taping, Kiki Shepard saw history unfold.

She was there to witness a 13-year-old Lauryn Hill get booed off the stage during a 1988 Amateur Night performance, only to return a few years later triumphant as a member of the multiplatinum Fugees. She saw white British vocalist Lisa Stansfield win over the Apollo crowd, proving color lines did not exist inside the hallowed theater. And Shepard was there when young, up-and-coming vocalist and composer Alicia Keys made one of her earliest televised appearances, debuting “Fallin’,” her breakthrough 2001 single.

For Money-B, who continues to tour with Digital Underground and is gearing up for the 35th anniversary release of the group’s classic debut Sex Packets, Shepard remains a boundless touchstone.

“I was just watching an episode of Everybody Hates Chris with my son, who is 11, the day before she passed,” Money-B said. “And Kiki Shepard happened to be in that very same episode. I pointed out to him who she was. It was important to explain what Kiki Shepard meant to the culture. She will always be the face of the Apollo.”

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