An illustration of multifaceted pianist Dorothy Donegan embedded in the title card for the Secret History of Chicago Music
Dorothy Donegan Credit: Steve Krakow

Since 2005 Plastic Crimewave (aka Steve Krakow) has used the Secret History of Chicago Music to shine a light on worthy artists with Chicago ties who’ve been forgotten, underrated, or never noticed in the first place.


Musicians who transcend genre and expectation often have to settle for being described decades later as “ahead of their time.” Multifaceted jazz pianist and vocalist Dorothy Donegan overcame racial prejudice, sexism, and musical gatekeeping to grow into her own bad self in the 1950s—to borrow a contemporary phrase, she gave zero fucks. She once described herself with the words “I’m wild but I’m polished,” and truer words were never spoken. Late in her life, Donegan began receiving the accolades she deserved, but given that she passed 25 years ago, I figure we’re all due for a refresher. 

Donegan was born April 6, 1922, at Cook County Hospital and grew up in Bronzeville at 4801 S. Evans. “My mother worked as a domestic and my father worked as a chef on the Chicago Burlington and Quincy Railroad,” Donegan told Dempsey J. Travis for his 1983 book An Autobiography of Black Jazz (excerpts of which I found on a Black travel guide to Chicago called Skychi). “They called my Dad ‘Bad Foot’ Donegan. He had real bad feet but he could bake his buns off.” 

Donegan started piano lessons in 1928. Her first instructor was Alfred Simms, who’d also taught the great Cleo Brown. Simms ran a music studio in his apartment at 5301 S. Calumet, and he charged a dollar per lesson, a fair amount of money back then.

“Simms was an excellent teacher,” Donegan told Travis. “He had me playing well enough after two years to do recital work, and before I reached the age of eleven he had brought me along far enough to do professional work as an organist and pianist in churches, lodges and house parties around the neighborhood.” 

In April 1998, shortly before her death, Donegan was interviewed by the Smithsonian for a jazz oral history program, and she explained how she knew the piano was her calling. “When I was eight years old, I could play all of Ellington,” she said. “And I think I recognized it then.”

Donegan’s cousin suggested she study with E. Sterling Todd, who played at the Savoy Ballroom at 4733 South Parkway (now King Drive). “He introduced me to the three B’s: Bach, Beethoven, and Brahms,” Donegan told Travis. “I devoured the classics at such a rapid pace that Mr. Todd suggested that I go downtown and study at the Chicago Conservatory of Music. . . . By the time I graduated from elementary school in 1935, I was considered both an excellent classical pianist and a very good jazz piano player.”

Donegan also learned from the legendary Captain Walter Dyett at DuSable High School, whose music program was a nursery for future stars—among them Dinah Washington, Johnny Griffin, Gene Ammons, and Von Freeman. The competition for the piano seat in Dyett’s booster orchestra was fierce, but Donegan ended up sharing it throughout her four years at the school with three estimable players: Rudy Martin, Martha Davis, and Earl Hines protege John Young, She recalled Nat King Cole dropping out of DuSable two months after she arrived to take his first band on the road.

Donegan remembered Dyett as tough but almost supernaturally talented. “He could hear a mosquito urinate on a bale of cotton,” she recalled. “He had such a terrific ear. Out of a 150-piece concert band, he could tell exactly which instrument had made the mistake, and you would know it because he would stare at you with that one good eye and make you feel smaller than a snail.”

For her earliest gigs, Donegan was chaperoned by her mother and brother. “We’d play for fish frys and rent scuffles,” she told the Smithsonian. “The ladies sometimes couldn’t pay their rent so they’d give a party and sell fish sandwiches for 15 cents. Chicken for the same. And that’s how they made their rent payments.” 

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“Piano Boogie” was the the A side of Dorothy Donegan’s first single, cut in 1942.

Donegan began playing at south-side clubs for a dollar a night when she was 14, and she learned very early that she preferred performing solo rather than as part of a band. As she later put it, “I like to steal a show mostly.” In 1942 she made her first commercial recordings, released by Bluebird Records. The hub label for “Piano Boogie” b/w “Every Day Blues” misspelled her last name as “Donigan.”

One of the many things Donegan wanted to accomplish was to play classical concert piano, and when she was barely into her 20s, she succeeded spectacularly—in 1943, she became the first Black artist to perform at Chicago’s Orchestra Hall, in what’s now the Symphony Center. 

“In the first half I played Rachmaninoff and Grieg, and in the second I drug it through the swamp—played jazz,” Donegan later told critic Whitney Balliett in The New Yorker (eventually collected in his 2006 book American Musicians II: Seventy-one Portraits in Jazz). “Claudia Cassidy reviewed the concert on the first page of the Chicago Tribune. She said I had a terrific technique and I looked like a Toulouse-Lautrec lithograph.” 

Media coverage of that concert—including in Time magazine—brought news of Donegan’s dazzling playing and wide repertoire to pianist Art Tatum, who then came to her home to hear her play. He taught her some of his techniques, and his style continued to exert a strong influence on her music. He respected her formidable talents, and he joked that she kept him on his toes. A 1983 issue of Ebony magazine quoted Tatum as having said Donegan was the “the only woman who can make me practice.” 

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Dorothy Donegan’s sole movie appearance was in the film Sensations of 1945.

Donegan would soon begin performing in New York and become a regular on the cocktail piano scene. In 1944, she landed a gig in the movie Sensations of 1945, where she’d appear alongside the likes of scat-singing star Cab Calloway and big-band leader Woody Herman. She left Chicago for Hollywood that year, taking her mother with her. Donegan appears in the film playing a barnstorming duel-slash-duet with pianist Gene Rodgers, backed by Calloway’s band. 

It would be her lone film appearance, unfortunately. Her agent at the time—she’d later call him “Corkscrew Gervish” because she considered him so crooked—refused a seven-year movie contract with MGM for $750 per week of work. Instead he accepted $3,000 per week for the Sensations production with United Artists, which lasted around ten days. 

Donegan would continue to release boogie-woogie 78s on the Continental label in the late 40s, including “Jumping Jack Special” and “Two Loves Wuz One Too Many for Me.” By the late 1950s, Donegan was gigging all over the country, perfecting her unrestrained, expressive style at clubs such as the Embers in Manhattan and London House in Chicago.

Despite a full performance calendar, Donegan had a rough road to success. She brazenly mixed swing, boogie-woogie, ragtime, gospel, blues, classical, pop, vaudeville, and more—and this expansive eclecticism, which she underlined with off-the-wall flourishes, confused and even angered some critics. They seemed to want her to fit neatly into a single box. 

The arts establishment found other ways to disparage and sideline Donegan too: because her witty, virtuosic shows were so thoroughly entertaining, she was frequently seen as merely an entertainer, not as an artist. And when she played for audiences who considered themselves “refined,” she caught flak for her uninhibited style. She often stood up at her piano, shaking her hips and stomping her feet. She liked to act out songs as she sang them, and she not only told off-color jokes but also peppered the music with allusions and history lessons—she might demonstrate the piano styles of Earl Hines, George Shearing, and Errol Garner or mimic the singing of Lena Horne, Pearl Bailey, and Billie Holiday. 

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Dorothy Donegan imitates Billie Holiday, Pearl Bailey, and Della Reese in this 1978 television spot.

For Donegan’s obituary in the New York Times, Ben Ratliff wrote, “Her flamboyance helped her find work in a field that was largely hostile to women. To a certain extent, it was also her downfall; her concerts were often criticized for having an excess of personality.” Donegan even had the audacity to insist she be paid the same rates as men.

Donegan moved to Los Angeles in the 1950s, and midway through the decade she began releasing LPs (the format had been introduced in 1948). Her first six albums—beginning with a self-titled disc in 1955 and ending with Swingin’ Jazz in Hi-Fi in 1963—included releases on high-powered labels such as Capitol and Roulette, but they didn’t make much of a splash. Though she would appear on The Ed Sullivan Show in 1965, playing “The Man I Love,” she wouldn’t release another LP till 1975’s The Many Faces of Dorothy Donegan

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Dorothy Donegan plays “The Man I Love” (with quotes from Rhapsody in Blue) on The Ed Sullivan Show in 1965.

Donegan was more comfortable onstage than in the studio, and for most of her career that’s how she made her living. Even when her records didn’t sell, she remained busy and beloved as a larger-than-life entertainer, and by the 1970s she’d developed a loyal fan base in New York—she broke attendance records with a 1980 appearance at the Sheraton Centre Hotel & Towers in New York. She played club dates and festivals across the U.S. and Europe, and in 1983 she appeared on Marian McPartland’s influential NPR radio program, Piano Jazz. She played a couple times at the Montreux Jazz Festival, and a recording of her 1987 set helped her belatedly develop an audience for her albums. 

That same year Donegan made her overdue debut at storied New York jazz club the Village Vanguard. John S. Wilson reviewed the engagement for the New York Times: “Miss Donegan has never let her show-business surface interfere with her virtuosity or her sensitivity as a pianist,” he wrote. “No one since Art Tatum has brought together a flow of running lines, breaks, changes of tempo and key, oblique references and rhythmic intensity as skillfully as Miss Donegan does.” 

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Dorothy Donegan performs at the White House in 1993.

As Donegan entered her 70s, she finally seemed to be earning recognition commensurate with her talent. She was awarded a Jazz Masters fellowship by the National Endowment for the Arts in ’92, and she played the White House in ’93. The following year she received an honorary doctorate from Roosevelt University, and in 1995 she made a guest appearance on Sesame Street, playing the blues with Hoots the Owl. During this period Donegan also lectured at several universities, including Harvard, Northeastern, and the Manhattan School of Music. Her last big show was in 1997, at the Concord Jazz Festival in the Bay Area.

It’s hard to know today if Donegan felt vindicated at the end of her life, or if she saw these honors as too little, too late. She died of colon cancer in Los Angeles on May 19, 1998. We can’t go back in time and undo the prejudices that kept her from the career she should’ve had, but we can keep spreading the word about her mad skills, her feminist fight for fair treatment, her stubborn defiance of convention, and her righteous personality.


The radio version of the Secret History of Chicago Music airs on Outside the Loop on WGN Radio 720 AM, Saturdays at 5 AM with host Mike Stephen. Past shows are archived here.

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