435 South
The Entertainer

It’s a full house by the time he takes the stage. Dressed in a gray flannel suit, black tie and vest and shiny black leather shoes, the entertainer tips his fedora politely toward the crowd. As the first words of Sinatra’s “Come Fly With Me” come melting out of his mouth, you can see the crowd taking it in. Toes begin to tap. One woman grins and elbows another next to her. Workers stop what they’re doing just to listen and watch him.

And while Greg Ashley Cooper, known in this circle as Ashley the Entertainer, could just as well be headlining at The Phoenix in downtown Kansas City every Saturday night, he is not. Today it is Friday, just after noon, and he is performing at The Atriums in Overland Park, a retirement community that has hosted him many times before. Cooper could be crooning to partygoers spending cash at cocktail-filled tables. Instead the entertainer prefers to work his way among the elderly audiences he loves, weaving an expert soft-shoe around a lobby filled with walkers and wheelchairs gloriously abandoned even if for just one hour.

“Songs can take you wherever you want to go,” says Cooper, who believes fully in music’s power to transport an audience — especially one with limited mobility — to a different time and place. 

Indeed, watching one of Ashley Cooper’s shows is like taking a step back in time. The entertainer sings, dances and reminisces his way through the 1940s and 50s with a polish that sets him apart from his peers. 

Memories are stirred with 40s classics such as Dean Martin’s “Baby It’s Cold Outside” and Sinatra’s “Fly Me to the Moon.” Cooper dances across the stage in Gene Kelly-esque fashion and tosses his fedora in the air and onto his head. When he talks about Big Band music in the 40s—“a time when lyrics meant something,” graying heads in the audience nod knowingly. Women smile as Cooper sings Elvis’ “Love Me Tender,” then laugh at his physical imitation of “Elvis the Pelvis.” And when his jacket comes off for 50s rock n’ roll dance numbers such as “Blue Suede Shoes” and “Shake, Rattle and Roll,” men and women alike get into the act by moving whatever they can—fingers, toes, walkers, entire bodies.

“I think these folks need to know that there’s a certain aspect to their past world that still exists today,” says Cooper. “That’s part of the reason I dress up for my shows and keep the language polite. It takes them back to a time when morals were good, and entertainment was clean.”

And while he talks about the past as if he were part of it, that’s hardly the case. An old soul at heart, Cooper’s physical age is surprising. He is just 26.

But Cooper seems to have an unusual sense of the two things that shape him—faith and music. 

“I was raised in a Christian household, and first and foremost that spills over into everything I do,” says Cooper. “My faith taught me how to treat people and how to care about them.”

As a Jehovah’s Witness, he grew up more insulated from popular culture than most. While his friends were listening to 2 Pac and Eminem, Cooper was singing along with his mother’s old vinyl records of Andy Williams, The Temptations and Bing Crosby.

“There was always music playing in my house,” says Cooper, who found he loved to sing and dance at an early age. “There was this one dance I did, and when people would come over, mom would say, ‘Do the dance, do the dance.’ And when I did it, everyone would laugh and have a good time.”

When Cooper grew up he worked stints in carpentry, selling cell phones and owning his own cleaning service before looking for another line of work to help support himself and his new bride. On staff at a retirement community, his mother-in-law suggested he try singing for seniors.

Initially, some retirement homes met his requests to sing with skepticism. 

“I remember one place I went, the woman just looked at me after I told her I wanted to sing there. ‘Our residents don’t like rap,’” she said to Cooper, who is African-American. 

But others were more receptive, particularly as soon as they heard Cooper sing. 

“I got one of my first jobs when a community manager sat down at the piano, started playing ‘Moon River’ and told me to sing,” Cooper recalls. “I sang a little and was surprised when he stopped, turned around and asked, ‘Okay. How much do you charge?’”

But if getting the job was one thing, performing was another. 

“I had never performed for anyone outside my family before,” says Cooper, who described his first show in November 2007 as the toughest hour of his life. 

“I just sat there and sang,” he says. “Later I noticed people staring at my feet, and that’s when I began to add dance to the later shows.”

Four months after that first show, singing and dancing for seniors became Cooper’s full-time job. Last year alone he performed 400 shows in the Kansas City metro area.

“Sometimes I can’t even believe that I’m here,” says Cooper about the unlikely career that he loves. “I’ve even been called by families to sing at the deathbed of a loved one who’s enjoyed my performances. I never thought in a million years that I would get to do something like that. I’m doing something that at the end of people’s lives is making a difference.”

The seniors who love Cooper’s shows use many adjectives to describe him — gracious, accomplished, polished. But woven throughout all of his performances is one unmistakable characteristic — an overwhelming desire to please his audience. 

 “You can tell that he enjoys watching us enjoying the show,” says Atriums resident and audience member Bessie Rudisill. 

Cooper wholeheartedly agrees. 

“If [my audience] doesn’t have a good time, I don’t have a good time,” he says. “I’ll even jump over stuff to sing to that one person in the audience who looks like they need a lift.”

Absent from Cooper is any bitterness that the very seniors he works so hard to please might once have denied people like his own grandfather a job or a place to live. 

“For me it’s like this: music of the 40s and 50s is the bridge that lets these two generations come together,” he says. “When we are together we’re not black or white, we’re not 80 or 26. The music closes the gap.”


words: Cisley Thummel

photo: Paul Versluis

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