Anita O’Day, 87, whose breathy voice and witty improvisation made her one of the most dazzling jazz singers of the last century and whose sex appeal and drug addiction earned her the nickname “the Jezebel of Jazz,” died of pneumonia November 23, 2006 at a convalescent hospital in West Los Angeles.

Ms. O’Day led one of the roughest lives in jazz, possibly surpassed only by her idol, Billie Holiday. Impoverished and largely abandoned in childhood, she became a marathon dancer and changed her surname from Colton to O’Day, pig Latin for “dough,” slang for money. In addition to marathon dancing Ms. O’Day also became what was known in dance circles as a “taxi dancer” or one who provided herself to dance with gentlemen who had no one else to dance with at dances.

Over a five-decade career, a mental breakdown, a rape, numerous abortions, a 14-year addiction to heroin and time in jail all contributed to her legend as a survivor. Her 1981 as-told-to autobiography was appropriately titled “High Times, Hard Times.” It is a fantastic and fascinating read and look into her life and career.

However, as a jazz singer her life soared. Jazz writer Nat Hentoff declared her “the most authentically hot jazz singer of all.” She remains at the top of the list of great female jazz vocalists.

In the 1940s, when most “girl singers” were pert appendages to a featured band, Ms. O’Day was a star attraction who often enlivened the orchestra with her playful and inspired vocals. She said she saw herself as an instrumentalist and often wore a band uniform instead of an evening gown. She was a far cry from terms like “canary” which were used to describe many female big band vocalists of the period.

Ms. O’Day was among the hippest female singers of the big-band period, lending rare emotional resonance to the relentlessly up-tempo and brassy big bands of Gene Krupa and Stan Kenton. She gave both orchestras their first million-selling hits, doing a rare interracial duet on “Let Me Off Uptown” with Krupa trumpeter Roy Eldridge and then the novelty number “And Her Tears Flowed Like Wine” with Kenton’s ensemble.

For Verve records in the 1950s, she performed some of the most inventive interpretations of jazz standards. Andy Razaf, who wrote the words to Fats Waller’s “Honeysuckle Rose,” once said hers was the definitive version of the tune — surpassing even Waller’s recording.

Ms. O’Day was sometimes compared to Billie Holiday, with whom she shared a tendency to project vulnerability through a calculated crack in her tone. She also was highly regarded for her scat singing.

Her signature sound created an elasticity with words, often breaking them into faster eighth and sixteenth notes instead of quarter notes, which were harder for her to sustain. This tendency was a result of a childhood tonsillectomy in which the doctor accidentally removed her uvula, the bit of flesh in the throat whose vibrations control tone.

To compensate, she would playfully stretch single-syllable words; “you” would be “you-ew-ew-ew,” love would became “lah-uh-uh-uv.”

“When you haven’t got that much voice, you have to use all the cracks and crevices and the black and the white keys,” she once said.

Ms. O’Day was born Anita Belle Colton in Chicago on Oct 18., 1919. Her father was a printer, and her mother worked at a meat-packing plant.

In the mid-1930s, she dropped out of school and hitchhiked to Muskegon, Mich., to enter a walkathon, one of the Depression-era crazes in which contestants were fed in exchange for brutal entertainment.

After some singing experience, she won a positive review in Down Beat magazine while performing in a downtown Chicago club with Max Miller’s band. Krupa hired her and Eldridge in 1941. The jazz writer Will Friedwald noted that the new additions “galvanized the Krupa men and positively transformed the band into one of the most powerful bands of the great era, putting it in a class with Duke Ellington, Count Basie, Benny Goodman and Tommy Dorsey.”

Her first million-selling record — and best-known early recording–“Let Me Off Uptown” paired O’Day’s sultry vocalizing with Eldridge’s raspy voice and roaring trumpet. The flirting between the white O’Day and black Eldridge was groundbreaking. “Do you feel the heat?” she asks Eldridge before instructing him to “blow, Roy, blow!”

Besides Krupa’s group, she also spent shorter and less-enjoyable stints with Woody Herman and Kenton, whose intellectual, “modern” sound did not mesh with her accent on easy swing.

The relentless performing on tour triggered a nervous breakdown, and over the next decade, she was jailed for marijuana and heroin possession.

She downplayed her arrests, writing in her autobiography that she “looked on serving my sentences as a kind of vacation. . . . Rehabilitated? Hardly. Rested? Definitely.”

In 1956, she was signed by Norman Granz’s Verve records, and the nearly 20 albums she put out during the next decade were among her most tantalizing, including “Anita” (with “Honeysuckle Rose“), “Pick Yourself Up,” “Anita O’Day Swings Cole Porter,” “Make Mine Blues,” “All the Sad Young Men” and “Travelin’ Light.”

She also played with Benny Goodman (who in the early 1940s refused to hire her because she was not disciplined enough to stick to a music chart), Stan Getz, Dave Brubeck, Count Basie, Louis Armstrong, Lionel Hampton, Joe Williams and Oscar Peterson.

She had a 32-year musical association with drummer John Poole, who she said introduced her to heroin.

Her vibrant appearance in the 1959 documentary “Jazz on a Summer’s Day,” a film about the 1958 Newport Jazz Festival, made her an international celebrity and brought her important dates in Japan and England.

Then, in 1966, she nearly died of a heroin overdose in a bathroom in a Los Angeles office building. The experience rattled her, and she quit heroin at once. Most of her money gone, she spent the rest of her life struggling financially. In the early 1970s, she was living in a $3-a-night hotel in Los Angeles but she revived her career over the next decade, culminating in a profile of her on the CBS news magazine “60 Minutes.”

She received her first Grammy nomination in 1990 for “In a Mellow Tone” and was given an American Jazz Masters award in 1997 by the National Endowment for the Arts.

When interviewed, her voice indicated an unyielding distress and frequent irritation. She told a reporter that alcohol provided a welcome relief for her at the end of the day. In 1996, permanent alcoholic dementia was diagnosed.

She played jazz dates until late in life–with embarrassing results as her frailties overtook her talent. But she was to be honored in March 2007 as one of the “living legends” of jazz as part of the Kennedy Center’s Jazz in Our Time festival.

Her marriage to drummer Don Carter, which she said was never consummated, was annulled. A marriage to golfer Carl Hoff, whom she called unfaithful, ended in divorce.

She said she never wanted children, telling People magazine, “Ethel Kennedy dropped 11. There are enough people in the world. I did my part by raising dogs.”

She dedicated her autobiography to her dog.

The article above was adapted from a piece printed in the Washington Post. Below is my personal remembrance and experience tracking Anita O’Day for the last half century.

My first brush with Anita O’Day’s singing was in 1985. It was my first year in radio as I had landed headfirst at a Great American Songbook and big band music radio station in Fresno. I was just beginning to buy jazz and big band LPs and doing research on jazz history (so I could at least sound like I knew what I was talking about). One of my “finds” at the local (now defunct) Tower Records store was a Columbia compilation LP (now on CD) called Jazz The 1940s: The Singers. On this LP was an intimate and innocent styling of the Hoagy Carmichael song Skylark. While intimate and innocent was not exactly what I was “into” at the time, being a child of rock and roll, this recording nearly brought me to tears. I still regard it as one of the songs that changed my tastes in music and gave me a new set of ears.

As time marched on I found a number of more upbeat recordings by Ms. O’Day and Gene Krupa’s big band. Songs like Let Me Off Uptown, Drum Boogie and Thanks For The Boogie Ride became favorites. Then delving deeper into the Krupa and O’Day years, corny novelty songs like Alreet, which used the hep jargon of the day, lent itself to my liking, as well as more inane lyrical treasures like Watch The Birdie and Stop, The Red Lights On. I’ll never forget my gleeful, yet guarded, reaction upon seeing the Soundie of Thanks For The Boogie Ride on a VHS tape a friend bought me for Christmas in the early 90s.

It’s really kind of incredible when you don’t grow up on jazz and begin to love the music and want to know about its rich history. Looking back on those early days, 21+ years ago, I still recall the excitement and wonder of finding out that Anita later recorded with Stan Kenton in the mid 40s. Not yet knowing about the Petrillo Recording Ban, the devastating effects of World War II to our country and to jazz, Gene Krupa’s drug bust (or staged police plant) I recall wondering about things like, what happened to Anita O’Day in 1943 between the years of her affiliation with Krupa (1941 –1942) and when her first (and last) recordings were waxed with Kenton in 1944.

But the Kenton years had suddenly come into view for me and recordings like Tampico, Ride On, Gotta’ Be Gettin’, Travelin’ Man and the ultra swinging, albeit kind of sad, And Her Tears Flowed Like Wine became the rave in my headphones. Questions like that would have to be answered at a later date, right now it was time to SWING!

Soon more historical puzzles beckoned. Stuff like; what the heck was a radio transcription disc and how could it be that Anita recorded some songs with Nat King Cole’s Trio in the middle of the aforementioned Petrillo recording ban of 1942 in May of 1945? What’s more, who put that session together and wasn’t Penthouse Serenade just about as subtly swinging and sensitive of a song as you’ll ever hear? Questions like these almost deserve to be left alone for future historical bounty hunters to uncover the same way, as did I.

But then what’s this? Anita O’Day recorded with Krupa again in August of 1945? Wow now there is a curious turn of events. No kidding, the great Sy Oliver arranged that recording of Opus One for them! Isn’t Boogie Blues just a solid hoot? And whose idea was it to lay down that really corny recording of Chickery Chick… way to unhip for Anita and Krupa. I guess someone needed to capitalize on the popularity of the tune, right?

Pieces of the puzzle began to fall in to place reading liner notes (with a magnifying glass) on the multitude of CDs I had been acquiring. Ah, but its outline became crystal clear after my best friend Dean Opperman mailed me a Christmas gift back in 1993. It was just a book. But not just any book. This was a real treasure. It was an autographed copy of Anita O’Day’s autobiography High Times, Hard Times. I was already obviously a fan of the vocalist… but I was to become hopelessly addicted now! Notwithstanding all of the insightful details of her career and life, to find that she shared many human traits that other unfortunates do, and was a fellow survivor… and thrived, well, that was just plain euphoric. Not to mention the fact that it gave me hope.

Still more superb recordings began surfacing in my ever-growing jazz collection. Anita with Oscar Peterson, Anita with Gene Harris and the Three Sounds, Anita with Buddy Bregman, with Billy May, Bill Holman… Waiter, Please Make Mine Blues while I go hang out with The Man With The Horn at Jazz On A Summer Day!

Anita O’Day man she can fit in with any set and any tempo. From a set of Big Band era music to a set of mainstream jazz, she is on time, in time, and at whatever tempo you need. She is at times torchy and seductive, at times serious and reflective, at times light, airy, and playful but she is always swingin’. Anita is a song stylist and jazz vocalist in a league only a handful fit in. She is in the same fraternity as Ella, Sassy, Frank, Billie, and Dinah. She is what a jazz standard is to jazz history.

At the risk of coming off like a sycophant or crazed fan Anita O’Day’s life and career touched me in a number of profound ways. Like a great improvisational jazz performance that will never, and can never, be repeated quite the same way again so I view her passing, enriched but wishing the experience would never end. To many who have yet to discover her career and life perhaps it may be similar. But for me Anita O’Day’s existence was “Like Sarah’s singin’.” “Like Yardbird’s swingin’.” “Like the minor’s gone, like the greatest song, that Eckstine’s ever sung, like a Moscow view, and oh so cool, like Lester Young.” “She was the high, in a Downbeat tally, like the guy, who owns Tin Pan Alley.” Like Tatum’s left hand, a Goodman swing band, a Lena Horne who won’t stop.” “But baby I’m the bottom you’re the top!” (Interpreted and adapted from You’re The Top – Anita O’Day acc. by Buddy Bregman’s Orchestra 12-8-1955) Jeff Parker – Swingmusic.org Radio