As Kathryn “Kay” MacDonald finished up the last two songs in her performance in Chicago, her eyes fixed toward the back of the auditorium. In walked a man surrounded by what in modern terms is referred to as an entourage. The year was 1944, and within moments she recognized what others around her already did— Duke Ellington had arrived. She left her place on stage and joined those down in the audience; pushing to get a closer look, when she finally reached him she was greeted with a question…

…“Can you be in Baltimore next week?” Ellington asked.

A week earlier, she and a friend attended one of Ellington’s performances. On a whim she decided to head backstage and after brief introductions she sang a tune. When she saw that Ellington seemed to enjoy it —and feeling even braver— she invited him to an upcoming performance.

“I was crazy about the man and his band,” Kay (now Kathryn Wimp) said in an interview with Northwestern Alumni News in 2001. “He was the epitome of style and class.”

She was pleasantly surprised that he had taken her up on her invitation— and even more surprised when he offered her a job. “I went home and packed my little trunk,” she said. “And that was the beginning of my career.”

The Formative Years

Born Kathryn MacDonald, in Evanston, Wimp knew early on in life that she wanted to sing. When her father, a chiropractor and her mother a homemaker from Evanston moved the family Bushnell, Ill. (62 miles outside of Peoria) she left behind a rich family history that included her grandfather, William H. Twiggs. An active civic leader, Twiggs was ahead of his time in working toward success in Evanston’s Black community. In 2000, this publication reported that he arrived in Evanston from Davenport, Iowa in 1884. He went on to own and operate a barbershop and printing press. Today, a park located south of Canal between Simpson and Payne streets bears his name.

Twiggs family c1912. Katherine Twiggs (Kay’s mother) far left

By the time Wimp arrived back in Evanston for high school her interest in music had piqued. “I remember singing ‘Trees’ in elementary school,” says Wimp by phone from her home in Florida. It was her first time singing in public. She also recalls that her father used to sing in a Catholic choir—and she credits that with being a major factor in her choice to pursue music.

In her last two years at Evanston Township High School, Wimp began taking voice lessons. The school was de-segregated because it was the only high school for students in Evanston, black or white. There, she was a student of Roy Schuzler, a music teacher at ETHS who happened to be a student of Northwestern University music professor Walter Allen Stults. The relationship she forged with Schuzler would prove beneficial when she enrolled as a voice major at Northwestern’s School of Music.

Back at ETHS, she joined a choir newly formed by the head of the music department. Wimp recalls walking into the rehearsal room to find the entire choir was Black. They were all perplexed, she says. The head music teacher, a white woman from Texas, explained that she thought forming an all Black choir was a good idea because she felt the Black students sang so well.

Wimp says they all walked out of the room.  And the notion of an all Black choir was soon dismantled.

There were other challenges that faced Blacks living in Evanston at the time. On Sundays she would go downtown with her two younger brothers and her parents to get ice cream, but they would eat it on the drive home because they weren’t allowed to sit in the parlor.

Once, when Wimp was a teenager she and a friend who was darker skinned attempted to eat in at a popular diner in downtown Evanston. The staff offered to serve the lighter skinned Wimp, but refused service to her friend. They eventually let them eat in, but according to Wimp they doused the food in salt. She and her friend cleared their plates and left. She proudly refers to it as their version of a sit-in.

Early Training

The first Black undergraduate to enroll and subsequently graduate from Northwestern was Lawyer Taylor. The Louisville-𝐛𝐨𝐫𝐧 Taylor enrolled at the age of 34 and graduated in 1903. Thirty-five years later Wimp enrolled at Northwestern’s School of Music majoring in vocal performance. Only six Black students were enrolled in the music program at the time and because of Northwestern’s policy at the time, students of color were not permitted to live in the residence halls.

“We used to drool over Willard Hall, which was right across from the music building,” Wimp said in 2001. “I had a good time at Northwestern, but there were those limitations.” Wimp says that the limitations placed on both Black and Jewish students forged a sense of unity. “We kind of bonded together,” she says.

But those years were not without controversy. In 1942 at Northwestern’s annual Waa-Mu Show, a showcase of the campus’ musical talents, Wimp sang a duet with fellow music major Jack Haskell despite the social taboos on cross-racial stage romance.

The Man and His Band

In 1943 Wimp graduated with a Bachelor’s degree in voice. The following year she received her Master’s degree. Then, the opportunity came to work with Ellington. One of her first experiences in Ellington’s band came when he taught her the simple melody to “Creole Love Song.” Within an hour she was onstage with him performing the song. The year was 1944. The place was Carnegie Hall.

“I sang, it got a wonderful ovation and then I got the heck off the stage!” she exclaims.

Her first recording with Ellington came about as he was teaching fellow band member Al Hibbler notes from “I Ain’t Got Nothin’ but the Blues.” Wimp sat humming along off stage. Ellington asked her to join in humming. When he eventually decided to keep her on the track Wimp was less than thrilled.

“I called home crying,” she says. She wanted to be on the frontlines.

Jet Magazine, Dec. 25, 1952

But there were plenty of opportunities to showcase her talent. The following year, in April 1945, President Roosevelt died. Ellington’s band was the only jazz band asked to perform for a national audience. One piece “A City Called Heaven,” was sung by Wimp. The years went on and according to Wimp band members came and went. Among those, the only still alive are Maria Ellington (of no relation to Duke), who later married Nat King Cole and gave 𝐛𝐢𝐫𝐭𝐡 to Natalie. She now resides in Florida. The second was Joya Sherrill who now resides in Great Neck, NY. But Wimp describes Ellington as a “genius” and says that even with constant flux of female band members he remained focused. She says, unlike many of his day he didn’t fraternize with female band members. In fact, he completely absorbed by his work.

“Music was his mistress,” she says. He was always at the piano. She even heard that later he bought a portable piano –presumably before they became a main stay– which he toyed with while on the road. She says he would stay up until all hours of the night “constantly composing” music.

The years between 1944 and 1950 were filled with high profile engagements, one-nighters and cross continental trips. Wimp describes life on the road as hard.

“It’s not that glamorous day after day,” she says. As time went on “I kept holding on hoping something dramatic would happen,” she says.

The band toured relentlessly, to the Palladium in England and with the Nicolas Brothers and Pearl Bailey in Liverpool, and seemingly everywhere in between. “It was quite an experience, very exciting,” she says. In 1947 the band toured California, Texas and Georgia.

It was a “whole different thing,” she says referring to race relations. She says they were bad, and despite their high profile they couldn’t even sit down in restaurants to eat. She recalls a frightening time in Macon, Georgia. The band had just finished a show and their manager, who was white, arranged a deal with a restaurant owner across the street from the theatre. Ellington and his band hastily made their way into the restaurant, so as to avoid any controversy. When a patron saw the band arrive he demanded to know why Blacks were being served.

The restaurant owner introduced Duke Ellington. And according to Wimp the angry patron answered, “I don’t care about no Duke Ellington!”

Before things could get any more tense, Wimp ran out of the restaurant and back to the concert hall where she set up a make shift hot plate. That night, she heated a can of Campbell’s soup over the sink in the ladies’ restroom.

Though things were rough at times, she and the band remained focused. But by 1950, after a four-week tour of Europe Wimp says, “I was tired. . . I got home and said, ‘That’s it,’” she says.

One night gigs and the relentless travel schedule began to take their toll. To this day she says feelings of fatigue remind her of those one-night summer gigs.

On the music of the day she says, “It escapes me.” But she is also encouraged by the recent resurgence of old standards from the likes of artists like Michael Buble, hailed as a modern day master of the music of yesteryear.

As for advice she gives to people aspiring to break into the music business. She says, “So much of what happens to you, no matter what you do is luck.”

Kay Wimp, visiting relatives in Chicago viewing artifacts Shorefront found in her 𝘤𝘩𝘪𝘭𝘥hood home in 2006.

She parallels this with the story of a 𝘤𝘩𝘪𝘭𝘥hood friend from Evanston who also graduated from Northwestern’s music school. Ann DeRamus was Black and studied classical piano. She was considered a prodigy by most, but breaking into the world of a classical pianist as a Black woman proved to be difficult. She went on to become a social worker.

But, Wimp adds that today, “If you’re really serious about something, no matter what you do, trust and have faith that it will happen.” She adds, “Look at me. I never dreamed that I would be on stage with Ellington.”