the Manhattan apartment building where she lived in 2004 a retirement home, but as of that time, neither self-destruction nor personal disaster nor the passage of eighty-four years could halt the indomitable Anita O’Day. This is the jazz singer who, starting in the ‘40s, made “cool” not only a sound but a way of life. And how did O’Day define cool? “That means doing everything that you like to do and getting away with it, you dig?”

O’Day pulled it off. After several near-death experiences, the woman once known as the Jezebel of Jazz was headed, in the summer of 2004, to play a week in London, followed by several nights in Paris. If her husky, throaty pipes now betrayed the thousand miles of bad road she’s traveled, that much-copied style – the frosted tone with a dash of vinegar; the blithe, airy rhythm that could make almost any band swing; the ultra-hip bebop vocabulary; the wisecracking insouciance that made you think all of this was just a lark – hadn’t left her. “Genes,” she explained.

Born in Chicago, O’Day became famous as a big-band singer. But much of her renown stems from the fourteen albums (1956-1962) she made for Verve. From the covers (which show her as a crisply tailored fashion plate) to the contents (an offbeat array of pop-jazz conducted by some of the field's greatest arrangers), those albums stand as a Bible of cool. Following the release of her and maestro Billy May’s salute to Cole Porter, Verve issued
Anita O’Day and Billy May Swing Rodgers and Hart (1960). “And swing the girl most certainly does,” raved Tony Brown in England’s Melody Maker. Hyper-energetic and whimsical, the album proves that she and May were meant for each other. Nobody wallows in sentiment; with May on hand, even the violins seem to smile.

On a muggy late-spring morning in 2004, I went to O’Day’s one-room apartment to see what she recalled about the album. Physical infirmities had slowed her down, and without drugs or booze (she was clean for the first time in her adult life), O’Day was less a chatterbox than before. But her feistiness and oddball humor remained. “We’ve been expecting you!” said the singer in mock-ladylike tones as she welcomed me in. Robbie Cavolina, her manager since 2000, was there to get her ready for the dentist and a fitting at Brooks Brothers. He announced big plans for her: new recordings, a documentary, a long-awaited biopic, more touring. She acted like she didn’t
care. As she'd recently told a reporter: “I’m not gonna get into that job-to-job thing until I’m ringa-dinga-ding. I just do a few, and then I go home.”

She was still a bundle of manic energy, and as Robbie worked on her champagne-blonde hair with a curling iron, she squirmed in her chair like a baby at feeding time. (Heroin, her drug of choice in the ‘50s and ‘60s, had helped calm her down then.) But as we played the Rodgers & Hart album on O’Day’s stereo – a Discman with little speakers – she listened intently. All the while she “conducted” with her nearly inoperative right arm, damaged in a drunken fall from her California trailer in the ‘90s.

I asked if she had picked any of the songs. “I think they just laid ‘em on me,” she said, shrugging. Five years earlier she had told me more: “I had them rehearsed at my house a couple of times so I could hear the structure. I learn the words as a poem, and I learn the chords the way it was constructed. The game is to put ‘em together, and don’t falter! But I had no chops, so I had to, like, fake it. And then I found out, like, the faking was better than doing the melody. Yes! There’s girl singers out there who sing melody. If you don’t like the way I sing, go listen to Patti Page.”

The Verve days fell during the prime time of her addiction, but in the studio O’Day took charge.
Melody Maker reported an exchange between her and trumpeter Don Fagerquist. “Stop! Stop!” she said angrily, pointing at him. “What’s the matter with you, man? You played exactly the same thing last time. Like, play something different, man!”

She also crossed swords with May (1916-2004), the rotund, grinning arranger from Pittsburgh. After apprenticing with the big bands, May went on staff at Capitol, where he provided swaggering big-band accompaniment on many albums, notably Frank Sinatra’s
Come Fly with Me. O’Day recalled their work together in a memoir written with George Eells, High Times Hard Times (1981):

......I sketched the tunes on tape and Billy embellished them for
......arrangements. Good deal, except that his music was too loud for and the engineer put us all on one track so remixing was
......impossible. I was always being buried … Once when I
......complained the strings were too loud on Rodgers and Hart, Billy
......bristled: “Get your own fucking orchestra.” Inside I flared, but
......outside I smiled: “Too late, Billy. I’ve already had my own band.”

By 2004 her opinions had mellowed. “Billy May was great!” she enthused. “Great, great. My voice is in front of the band! It was easy. Of course, I was smoking pot!”

Richard Rodgers, who couldn’t bear anyone tampering with his music, would probably have hated her boppish reconstructions of "Have You Met Miss Jones" and "Lover." But compared to the more formal, stately work he did later on with Oscar Hammerstein II, Rodgers’s songs with Lorenz Hart were harmonically freer and ripe for improvisation. Their partnership, which lasted from 1919 until Hart’s early death from pneumonia in 1943, was turbulent. Hart, a four-foot-nine, cigar-chomping New Yorker, agonized over his height, his homosexuality, and his near-loveless existence. He drank himself blind and drove Rodgers crazy with his unreliability. But his words – chatty yet impeccably crafted, urbane, and full of feeling – set the bar high for nearly every songwriter to come. Hart poured his anguish into some of the most emotionally naked lyrics ever written; he could also view love through the starry eyes of a schoolboy.

None of that was O’Day’s style. But the playful, witty side of Hart gave her plenty to connect with. She had fun with "To Keep My Love Alive", the comic confession of King Arthur’s murderous sister, written for the 1927 musical
A Connecticut Yankee. O’Day turned two of its stanzas into a hilarious spoken monologue: “I thought Sir George had possibilities/But his flirtations made me ill at ease/And when I’m ill at ease, I kill at ease!” She relished the short, snappy phrases of a Depression-era pick-me-up, "I’ve Got Five Dollars," in May’s lighthearted circus-y setting. He conducted "Johnny One Note" as if it were a roaring freight train. O’Day rode it with ease, right down to her machine-gun, monotone tag. “The arrangements are making me so happy!” she said as Robbie rubbed cold cream on her chin.

Performing "Ten Cents a Dance", a 1930 forerunner of Tina Turner’s “Private Dancer,” O’Day sounded more amused than tragic. On four ballads with strings – "Little Girl Blue," "Spring Is Here," "It Never Entered My Mind," "Bewitched"
– O’Day sang with a half-smile and only a trace of wistfulness. (“I’m not a ballad singer,” she always said, rather proudly.) She pointed out a bebop run she sang at the end of "Bewitched": "I made that up right there – doo-ooh-ooh. Then I forgot it."

Robbie chimed in: “Anita’s approach to these songs was just so different than anyone else’s. Like 'Little Girl Blue,' everybody drags that song. And that’s one thing that Billy May really knew about Anita, he knew how to write for her tempo ability. The strings aren’t emotional, sappy.” O’Day herself certainly wasn’t. As she put it to me in 1999: “My pain? I never had any pain. I was always high!” Indeed, once she finished singing, said Robbie, she left before hearing the playbacks and ran out to score.

She’d done her job. As Tony Brown wrote in the June 10, 1961 issue of
Melody Maker: “Anita’s interpretations of the familiar songs are highly sophisticated, yet they are alive with warmth and humor … the O’Day brand of hip cynicism brings out the latent and barely suspected irony in some of those inspired Larry Hart couplets.”

As the last song played, Robbie struggled to glue eyelashes on the now-cranky singer. “We can’t go yet!” he said.

“What would you do if I was

“It would be easier,” he answered, laughing, “because you’d hold still!”

Finally, looking much like the O’Day of old, she glimpsed herself in the mirror. “Not bad!” she said.

As they got ready to leave, I asked if she had ever imagined that so many of her albums would one day be seen as masterpieces. The thought didn’t phase her. “I don’t understand what everybody’s hoop-de-dooing about,” she said. “I just do what I feel. And if I get the right help, it’s better.”