Mildred Bailey

The most famous jazz singer you've never heard of

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Ok, I confess. Up until three years ago, I was unfamiliar with Mildred Bailey. Shame on me. I deejay a weekly radio show that features artists of the 30s through the 50s. Why had I never come across her? I sat up and took notice in 2023 when engaged in an absolutely enthralling Apple tv series called “Lessons in Chemistry.” The show’s title music during the opening credits was the 1940 recording “Wham (Rebop Boom Bam) sung by Mildred Bailey and backed by Roy Eldridge and his Orchestra. In case you missed it, here is the intro with its visually appealling credits and snappy swing song sung by Mildred Bailey.

I am unsure why the producers chose the song, but it certainly sets the mid-century vibe and the important place jazz music held for its protagonist Elizabeth. And, the lyric “I’m a killer diller, yes I am” perfectly describes her character.

I had to know more about the tune and Mildred Bailey. Talk about a “killer diller!” Mildred Bailey definitely filled those shoes. Born in 1903, she grew up on the Coeur d'Alene Reservation in Idaho until she was 13. Her mother was part Native-American. She had a musical childhood playing piano and singing with her family. Due to an unhappy homelife (and abusive stepmother), at 17 she moved to Los Angeles and immediately secured gigs at local speakeasies and jazz clubs. Not long after, her brother Al Rinker showed up from Spokane with his good buddy Bing Crosby seeking work in the music business. Mildred got them an audition with the Fanchon and Marco theatrical company that sent them on a vaudeville tour of nearly 40 West Coast theaters. Not long after, Al and Bing were noticed by Paul Whiteman and were hired by him to sing with his popular dance band as two-thirds of The Rhythm Boys. This opportunity sent Bing Crosby’s career on a rocket-like trajectory, and he never forgot the favor done for him by Mildred Bailey. Their careers would continue to cross paths over the next 20 years.

Mildred Bailey is credited as the very first female big band vocalist and one of the earliest female vocalists to sing ahead of and behind the beat. In the 1920s, a woman singing in a dance band was an anomaly. Bailey was hired by Paul Whiteman in 1929 thanks to - you guessed it - her brother Al and Bing Crosby who engineered her introduction to Whiteman at a Hollywood party. (she was chosen over Hoagy Carmichael, who had just auditioned for Whiteman that very week!) That turned out to be an historic moment in jazz history, as other dance bands began to copycat the addition of a female vocalist in their own ensembles. Those that came after her, from Billie Holiday to Doris Day, owed her big time.

Her vocal inspiration was Bessie Smith, the great African American blues singer. Imitating her style, she sounded both white and black and her popularity grew from her radio appearances as she appealed to both audiences. She had a light soprano voice, excellent diction, great jazz phrasing and an easy, laid back demeanor that audiences loved.

“Sheet music was hard to get,” she said, “and a tune had to be [memorized] from a recording. I could never get the exact notes of a song, so I used to scheme out the best way to sing it smoothly. Sometimes I would think how a tune might have been improvised if the composer had changed certain parts ... and I would try singing it in my own way. It sort of stuck this way through the years, and before I could straighten myself out ... I found out they were calling this swing and liking it.”

She stayed with the Whiteman band until 1933 when she married Whiteman’s vibraphonist Red Norvo and moved to New York where the two of them were featured on CBS radio and recorded extensively. Known as “Mr. and Mrs. Swing” they divorced in 1942, but remained friends and continued to collaborate musically througout the 1940s.

Mildred Bailey and Red Norvo, “Smoke Dreams” (1937) Critics claim this was their best work together.

By far, Bailey’s biggest hit was “Old Rockin’ Chair” written by Hoagy Carmichael and debuted by her on a Chicago-based live broadcast of Whiteman’s weekly Old Gold radio show. It was so very popular, a studio recording was made and she became known as “the Rockin’ Chair Lady” for the remainder of her career. (I suppose that more than made up to Hoagy for taking away his vocalist spot with Paul Whiteman!)

1937 recording of “Rockin’ Chair” with Mildred Bailey and Red Norvo.

She was a superstar in the 1930s and 1940s working with some of the most famous big bands of the era. She had three Downbeat magazine cover stories between 1937 - 1942. No history of jazz singing would be complete without Mildred Bailey.

Her impact cannot be dismissed. She greatly influenced those jazz singers that followed her. Tony Bennett said of her “From 16 to 20 years old the only thing I listened to was Mildred Bailey. I just said I want to sing like her.”

She served as a mentor to the young Billie Holiday, introducing her to her own producer John Hammond. Both Bailey and Holiday shared accompanist Teddy Wilson who said that "Mildred Bailey was a much better singer than Billie." Duke Ellington praised Bailey's timing, and Bing Crosby credited her with teaching him all about vocal phrasing.

Her biggest success was in the 1930s and 1940s. But health issues (diabetes) plagued her in her later years and in 1951 she died at the age of 44.

It is unclear why her legacy has been all but ignored. Attempts have been made in more recent years to recognize her importance to jazz. Her entire Columbia Records catalogue is available as boxed sets in both LP and CD formats. Bailey was inducted into the Big Band and Jazz Hall of Fame in 1989. Her contributions to jazz were commemorated by a United States Postal Stamp issued in 1994.

I am glad to now know her story and her important contribution to jazz. Here she is, the “killer diller” herself in 1938, telling the world “I was Born to Swing.” Indeed she was.

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Further reading:

https://www.allaboutjazz.com/news/mildred-bailey-queen-of-swing/

https://www.historylink.org/file/7445

https://syncopatedtimes.com/mildred-bailey/#:~:text=At%2017%20she%20married%20Ted,dubbed%20him%20%E2%80%9CPops%E2%80%9D).

https://postalmuseum.si.edu/exhibition/women-on-stamps-part-4-prominent-female-singers/a-swingin-time-mildred-bailey#:~:text=Mildred%20Bailey%20(1907%2D1951),started%20their%20own%20radio%20show.

https://en.wikipedia.org/wiki/Mildred_Bailey

https://downbeat.com/news/detail/mildred-bailey-belated-accolade#:~:text=I%20could%20never%20get%20the,%2C%20%E2%80%9CRockin’%20Chair.%E2%80%9D&text=This%20story%20originally%20was%20published,Subscribe%20here.

https://wicn.org/wicn-artist-of-the-month-november-2025-mildred-bailey/#:~:text=Mildred%20Bailey%2C%20often%20called%20the,become%20a%20skilled%20jazz%20singer.

https://jivetimerecords.com/northwest/mildred-bailey-xxx/