ANITA O’DAY – “First Lady Of Swing”

“Anita O’Day is demonstrating at The Blue Note why she is one of the little handful of great stylists among Jazz singers. She can give any song her unmistakable imprint…The girl is so modern she’s almost ahead of herself. Her minor keys and off-beat phrasings have a weird otherworldliness…”

  • Chicago Sun-Times

“She was an original, and there’s very few of them in this life. Nobody sang like that before her, but a lot of people tried to sing like that after her.”

  • Songwriter, arranger, and band leader Johnny Mandel

From her own viewpoint, Anita O’Day was emphatic in saying that she was not a singer per se but rather a song stylist. O’Day, whose idols were 30’s Native American Jazz singer Mildred Bailey and comedic actress and singer Martha Raye, admitted to copying Billie Holiday for a long time before establishing her own sound and style. That style revolved around using her voice like a musician uses their instrument. Studying the phrasings and forays of sax players like Stan Getz and Zoot Sims, O’Day was a supreme improvisor. She fashioned lines of rapid-fire syllables, bending and twisting lyrics and melodies. And like any Jazz musician, she would never perform a song the same way twice.

Further, as O’Day explained in a NY Times interview: “I’m not a singer because I have no vibrato*…If I want one, I have to shake my head to get it. That’s why I sing so many notes so you won’t hear that I haven’t got one. It’s how I got my style”.

*O’Day’s lack of vibrato was attributed to a botched tonsillectomy when O’Day was 7 years old. It would be many years later that Anita came to the realization as to the cause of her not having vibrato.

Anita O’Day was often promoted as “The Jezebel Of Jazz” – no doubt primarily due to the high profile drug busts that punctuated her time in the world of Jazz. But there’s more. The moniker also alluded to the fact that Anita O’Day marched to her own drumbeat. She was a hip talking non-conformist who lived for and lived in her music. Like her contemporary Ella Fitzgerald, O’Day only knew true joy on stage and couldn’t reconcile life when she wasn’t performing. And like Ella, O’Day enjoyed a long career; (Anita’s lasted 7 decades; Ella’s lasted 6).

Anita’s life was her art and her art was her life. Any obstacles were dealt with as required to serve her singular devotion to that art with no looking back. By some accounts, Anita lived a lonely life. What’s for sure, for all intents and purposes, O’Day lived her life on the lam, never having money or success commensurate with her obviously abundant talent. Her’s is a story of survival and an endurance of that talent till her last days. Simply put, Anita O’Day was one of America’s greatest Jazz singers; and she can rightfully be mentioned in the same conversation as the A-list: Ella Fitzgerald, Billie Holiday, Sarah Vaughan, and Carmen McRae.

Anita Belle Colton was born in Kansas City Missouri on October 18, 1919 and moved to Chicago as a young child. Prompting the move was the fact that Anita was born out of wedlock; and as a consequence, her parents were looking to both avoid scrutiny and hoping for a fresh start in a new town. It was an unwanted pregnancy leaving Anita forever scarred; sensing that she was – in her words – “excess baggage”. It was a feeling perpetuated by a mother’s lack of affection and a father who ran out on the family not long after settling in Chicago. To cope, at a young age, Anita learned to be self-reliant, and hid any related pain under a tough, cynical veneer. (Later Anita would turn to alcohol and drugs to numb any suffering associated both with her loveless childhood and the rigors of the life that she had chosen).

Anita, whose “biggest dream was to be a singer”, started on that road at 12 years of age. At 14 she left home to compete in marathon dance contests that were popular during the Depression. O’Day entered this phase of her life with her eyes wide open. She was well aware of the gruelling hours that she signed up for – staying on her feet for days / nights at a time. She also knew that the bare necessities, (e.g. meals), would be provided along with the opportunity to make more money than anyone that, like her, lacked a formal education. Directly in line with that thinking was Anita’s decision to change her name from Colton to O’Day explaining “I decided that O’Day was groovy because in Pig Latin it meant dough, which is what I hope to make”.

It was during one such marathon that O’Day was asked to sing. “Waiting for this moment my whole life”, Anita responded with a rendition of Al Jolson’s “Is It True What They Say About Dixie”. The song was met with applause, stamping of feet, and an appreciative shower of coins. Anita viewed the moment as a jumping off point to her dream. But, in reality, it was a hint of the success that would only be achieved after a long hard road that lied ahead. That road included three more primary stages: chorus girl, Big Band singer, and finally Jazz singer in her own right.

Returning to Chicago, and confirmed to becoming a singer, Anita started on her quest by working as a chorus girl in uptown locations such as The Celebrity Club and Vanity Fair. That was followed by a stint as a singer/ waitress at various clubs. (One such venue, The Vialago, was where Anita met her first husband, drummer Don Carter. Although the marriage would only last a year, Carter furthered her career by introducing O’Day to music theory).

In 1938, at age 19, Anita started guesting with various bands at clubs around town when DownBeat editor Carl Cons hired her for his new Off-Beat Club. The club quickly became a hangout for Jazz musicians of all stripes. Flashy and charismatic drummer Gene Krupa, on a tip, decided to check her out. Impressed, Krupa promised to call Anita if his current vocalist, Irene Daye, ever left the band. It took 3 years, but after the call finally came in 1941, Krupa and O’Day started to make Big Band history. 

Anita, would do two year-long stints, (1941 and 1945 respectively), with the Krupa band early in her career. She was hired as a featured female vocalist as was the custom with Big Bands. That is, Big Bands would employ a female singer, (or “canary” as they were termed in the day), as a change of pace, performing a limited number of songs in the course of an evening. It was an accepted glamour role with the singer usually dressed elegantly with a strapless or flowing evening gown. This was in stark contrast to the musicians in the band who would be dressed in matching band uniforms, (jacket and trousers). Once established, O’Day, knowing full well that she had a lot to offer musically, balked at being perceived as just “the girl singer in the band”. Instead, she insisted that, as part of the band, she be allowed to dress as the members of the band. In so doing, O’Day was a trend setter appearing with a jacket and either a skirt or trousers. Anita wasn’t pursuing an agenda or making a statement as such, she was just being herself. (Although it wasn’t lost on all concerned that O’Day wanted to be treated as a musician and an equal to the rest of the band).

In the two terms that O’Day served with Krupa she would record 34 sides and 5 hits. Those hits would include two duets with impressive trumpeter Roy Eldridge who was hired at about the same time that Krupa hired Anita. O’Day and Eldridge had a natural chemistry that paid dividends on both tracks: “Let Me Off Uptown” and “Thanks For The Boogie Ride”. The first, “Uptown” – that sold more than 100,000 copies – not only made Anita a star and boosted the popularity of the Krupa band; it stands as ground breaking in that it also was one of the first interracial duets on record.

The audience and the media took notice. O’Day, who Krupa described as “…a wild chick but how she could sing”, was named as “Outstanding New Star” in an Esquire poll. At the same time, DownBeat named her “New Star Of The Year”. A year later DownBeat would select Anita as one of the top five Big Band singers. (Anita would place fourth behind Helen O’Connell, Helen Forrest, and Billie Holiday; and ahead of Dinah Shore). Lastly in 1945, having rejoined Krupa, DownBeat named her “Top Girl Band Vocalist”. These were the first of many more accolades that would be bestowed on O’Day in the course of her lengthy career.

Anita would continue with singing with other Big Bands after leaving Krupa including those led by Stan Kenton, Benny Goodman, and Count Basie. While having some moments, e.g. a # 4 hit with Kenton “And Her Tears Flowed Like Wine”, O’Day’s career and popularity went to the next level when she launched her solo career in the late 40’s, (usually opting to perform in live settings with a trio that allowed her room to experiment and improvise). This is especially true during the 50’s that defined Anita’s career.


Given that her popularity and success surged and sagged in unison with her continued dependency on drugs and alcohol it may be best to get this element of her life out of the way so that we can concentrate on Anita’s artistic endeavours. Anita was busted for pot possession in 1947 and 1952, and for heroin possession in 1953 when she served 6 months in jail. O’Day started smoking pot when she was young (and it was still legal). And, given her surroundings and the times, alcohol was always readily available to her. Further, not to give her a pass, but the truth is that as a heroin user, she didn’t take advantage of those close to her to the degree that others had in order to feed her habit, (like, for instance, a Chet Baker). Rather, the only person she really harmed was herself, denying herself not only of consistently good health, but also of fame and fortune. Anita estimated that she spent close to $400,000 on heroin in the course of her career. And living a junkie life, in the 15 years that she was addicted – 1952 through 1967 – her daily objective to score was all consuming. O’Day needed a fix to simply maintain the required bodily chemical balance so that she could function somewhat normally. It was only after a near death overdose in 1967 that Anita kicked the habit cold turkey. Reflecting on those years in a 1973 interview with the L.A. Times O’Day summed it up this way: “The narcotics thing was just there. It was what was happening and it kept me in and out of trouble for 20 years”.

As a last point on the subject, while enablers played a role, the perception in the 40’s and 50’s specifically was such that the Jazz life was viewed as synonymous with drug use. Accordingly, to put things in perspective, in the course of drug enforcement, Jazz artists were tailed and hounded continually. And, on more than one occasion, it was proven that informants were sent to plant evidence on musicians thereby ensuring an easy bust.

Anita’s career took flight when Norman Granz signed her to his Verve label in 1952. (A year after Anita’s first substantial solo success with a cover of Patti Page’s “Tennessee Waltz”). Granz started the label primarily as a platform for Ella Fitzgerald. In addition to Fitzgerald, (who didn’t use drugs of any kind), Granz built his label on artists that other companies wouldn’t touch because of their respective drug histories. Such notable Verve artists included Jazz giants Lester Young, Charlie Parker, and Billie Holiday.

For her part, Anita recorded some 17 quality albums for the label with both small group and larger ensemble settings. To everyone’s mutual benefit Granz allowed her more say in the material that was recorded as well as how it should be presented. None put her talent on full display more than Anita (released 1955), Anita O’Day Sings The Most (1957) and Anita O’Day Sings The Winners, (1958). Anita features O’Day’s unforgettable takes on standards such as “You’re The Top”, “Honeysuckle Rose”, and “A Nightingale Sang In Berkeley Square”. “The Most” matches O’Day with the Oscar Peterson Quartet – his regular trio is augmented with O’Day’s long time platonic musical partner John Poole on drums – on a set that includes O’Day’s special treatment on standards like “They Can’t Take That Away From Me” and “Them There Eyes”. “The Winners” features covers that O’Day has been long associated with like Billy Strayhorn’s “Take The ‘A’ Train” and “Sing Sing Sing”, a Louis Prima composition that Benny Goodman turned into a classic Swing hit. Also included is an outstanding take on Woody Herman’s instrumental “Four Brothers”. In this instance, because there are no lyrics, O’Day was given only sheet music and left to her own devices. As such, Anita – whose improvisational skills are legendary – proceeds to give a graduate course in scatting that’s nothing short of amazing. Her interaction with the horns is such that her instrumentally inspired lines are virtually interchangeable with theirs.

Although struggling with her addiction, that caused periods of inactivity, O’Day remained popular, securing high profile club gigs and festival dates, (usually in the company of other featured Jazz greats). One such festival appearance was the 1958 Newport Jazz Festival where she shared the stage with the likes of Louis Armstrong, Dinah Washington, and Miles Davis. Many critics cite Anita’s performance – that made her an international star – as the highlight of her career. (At the very least it opened doors to global markets – especially Japan where Anita returned for well received shows and festival dates numerous times starting in 1960). Anita performed both an afternoon and evening show on the closing Sunday backed by a trio including John Poole on drums. Two songs from her nine song afternoon set are captured in the film “Jazz On A Summer’s Day”. Anita is a striking figure in high heels, a tight black dress, a matching wide brimmed hat with ostrich feathers, and long white gloves. Not only is she impeccably dressed; despite, (in her own words), being, “high as a kite”, she lays down a version of “Tea For Two” at breakneck speed and a take on “Sweet Georgia Brown” that Newport producer George Wein lauded as the best rendition of the song ever. Her performance rivals all others’ featured in the documentary.

As the 60’s approached Anita would continue to record and tour but the effects of the substance abuse were starting to take its toll. It’s safe to say that her career nosedived as her heroin addiction effectively took control of her life. Compounding the issue, after her overdose in 1967, O’Day started to experience heart problems as a result of her heroin use.

But the ever resilient O’Day made a comeback in 1970 at 51 years of age. A highly acclaimed performance at the Berlin Jazz Festival effectively got her career back on track. Starting with a live recording of her performance at the Berlin festival, Anita would release 8 albums in the decade proving that even as her considerable vocal skills were diminishing, she still had a lot to offer her legion of fans. And given how interwoven her life and music were, Anita acknowledged the support and encouragement of those fans despite her personal battles:
“Without them you’re nothing…That’s where my heart lies. That’s all I’ve got. I had a couple of boyfriends. Duds. A Couple of husbands. Gone. But you always get something back if you give. That’s never changed”.

The 80’s kicked off with the release of her autobiography High Times Hard Times that made the New York Times best seller list. It’s a no holds barred account of both Anita’s joys and hardships. Although documenting O’Day’s triumphs, the book is chilling with stories of sexual assaults, backroom abortions, and failed marriages. On a brighter note, the 80’s were also marked by a stellar performance in 1985 concert at Carnegie Hall celebrating Anita’s 50 years in Jazz.

Settling in Los Angeles, O’Day wasn’t done yet. Anita released 12 more albums in the 80’s and 90’s. (Her last release, appropriately titled Indestructible, hit the streets in 2005 – when Anita was 86 years old!). And she remained a popular live attraction in her adopted home until the end of her life.

Anita O’Day lived a full, albeit hard, life on her own terms. She was constantly crashing, and learning to stand up again. She always appeared to be struggling despite her brilliance as evidenced by her earnings that swung from $2,000 a week to $200 a week at various junctures in her career. But, in all, she persevered and survived. Following continuing health issues Anita died in her sleep on Thanksgiving Day, November 23, 2006.

Anita O’Day was once defined as “The greatest white girl Jazz singer in the world”. Anita legitimately earned the title and also paid the cost.

A Selected Anita O’Day Playlist

  1. Georgia On My Mind
  2. Let Me Off Uptown
  3. Thanks For The Boogie Ride
  4. Just A Little Bit South Of North Carolina
  5. Ain’t Misbehavin’
  6. And Her Tears Flowed Like Wine
  7. Boogie Blues
  8. Tennessee Waltz
  9. You’re The Top
  10. Honeysuckle Rose
  11. A Nightingale Sang In Berkeley Square
  12. Stompin’ At The Savoy
  13. ‘S Wonderful / They Can’t Take That Away From Me
  14. Them There Eyes
  15. Love Me Or Leave Me
  16. Take The “A” Train
  17. Easy Come, Easy Go
  18. Bewitched, Bothered And Bewildered
  19. Do Nothin’ Till You Hear From Me
  20. The Ballad Of The Sad Young Men
  21. Johnny One Note
  22. Four Brothers
  23. Tea For Two
  24. Sweet Georgia Brown
  • Rico Ferrara, March 2022