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From the ’30s through the mid-’50s, jazz singers learned their craft by touring with big bands—Mildred Bailey with Paul Whiteman, Billie Holiday with Count Basie and Artie Shaw, Ella Fitzgerald with Chick Webb, Peggy Lee with Benny Goodman, Frank Sinatra with Tommy Dorsey, Sarah Vaughan with Earl Hines and Billy Eckstine, Jimmy Rushing and Joe Williams with Basie. Of the great orchestra leaders, only Duke Ellington failed to produce a vocalist who enjoyed a stellar solo career after leaving the band, probably because Duke didn’t want singers overshadowing his instrumental compositions.

Stan Kenton headed one of the few jazz orchestras that survived the postwar collapse of the big-band era; his innovative, bombastic ensembles thrived until the bandleader’s death in 1979. Although best known for commissioning and performing unconventional charts by cutting-edge arrangers, Kenton also spawned a highly individualistic school of female singers. Joining Kenton in 1944, Anita O’Day, fresh from a successful, two-year run with Gene Krupa’s less adventurous swing band, was the progenitor of this style, followed in turn by June Christy from 1945 to 1949, and Chris Connor from 1952 to 1953.

This year, Connor, now a jazz icon, begins her sixth decade as a professional singer, a milestone marked by the release of Warm Cool, a two-CD compendium of some of her finest recordings, and her appearance Saturday evening at the Kennedy Center’s “Women in Jazz” festival. In the music business, where performers who have recorded more than two albums are commonly referred to as “legendary,” Connor is the real thing. Miraculously, time has not diminished the quality of her work. As the Penguin Encyclopedia of Popular Music accurately observes, “Her voice is as good as ever, interpretations maybe even better.”

Kenton songbirds shared certain strengths and liabilities. They had husky voices—perhaps the consequence of struggling to make themselves heard above Kenton’s blaring brass sections—without a trace of coyness and delivered lyrics with cool detachment. Unlike Holiday and Lee, they were concerned less with directly projecting emotions than with expressing feelings reflectively, an approach well suited to the buttoned-up ’50s. The jazz public adored them, but reviewers consistently complained that their work suffered from patches of questionable intonation.

After leaving Kenton, all three singers became concert and jazz-club headliners and enjoyed long, successful record label affiliations: O’Day with Verve, Christy with Capitol, and Connor with Atlantic. Since the advent of compact discs, many of O’Day’s and Christy’s albums have been reissued, but curiously, given Connor’s popularity and the fact that she continues to perform widely in the U.S. and abroad, only three of her 11 Atlantic albums have been domestically resurrected—a two-disc George Gershwin songbook and a twofer combining Chris Craft and A Jazz Date. Warm Cool addresses this oversight, its 40 tracks collating nearly a quarter of the material she recorded during her seven-year association with the label.

Connor began her musical career as an instrumentalist, studying clarinet for eight years before singing with a University of Missouri band headed by her classmate, trombonist-arranger Bob Brookmeyer. After college, she joined Claude Thornhill’s orchestra, first as a member of his vocal group, the Snowflakes, and subsequently as the band’s solo singer. (During this period, she maintained her clarinet chops. At one performance, she grew so exasperated with clarinetist Tony Scott, whose backstage behavior annoyed her, that she snatched his instrument from him and played his feature number—Artie Shaw’s “Concerto for Clarinet”—herself.) After two years with Thornhill, she accepted an offer from Jerry Wald’s band. Christy, preparing to leave Kenton, heard Connor singing on the radio and recommended her as a replacement.

Connor lasted only 10 months with Kenton; she found his one-nighter road schedule too punishing. But her hit single with the band, the moody ballad “All About Ronnie,” secured her a contract with the fledgling Bethlehem label, for whom she recorded three successful LPs. These records, in turn, led her to Atlantic and the treasures contained in the aptly titled Warm Cool.

Connor’s most distinctive qualities are her daredevil sense of time and her unusual sound. She swings at all tempos, sometimes racing so far ahead or lagging so far behind the beat that you fear she’ll never reclaim it—but somehow she always does. The complex timbre of her voice is difficult to describe; it’s misty yet strong, slightly strained but mellow. Her deep tones are particularly compelling, at times reminiscent of a cello or French horn. (“Follow Me,” featuring violinist Harry Lookofsky’s violin obbligatos, shows off the richness of her lower register.) She takes a similarly ineffable approach to lyrics, particularly her readings of melancholy ballads. Never indulging in overt emoting, she imbues rueful love songs (“Something to Live For,” “Here’s That Rainy Day,” “Good Morning Heartache”) with a bruised, introspective quality. She shares with her ’50s movie counterpart Kim Novak a stolid but vulnerable sensibility, implying that she knows much more about pain than she’s willing to articulate.

Warm Cool, handsomely packaged with photographs of Connor at several stages in her career and reproductions of her album covers, reveals how imaginatively and generously Atlantic showcased her talent, surrounding her with large ensembles (string orchestras arranged by Ralph Burns and Jimmy Jones, and brass ensembles including Maynard Ferguson’s and Count Basie’s bands) and smaller groups comprising of top-flight jazz instrumentalists, among them Phil Woods, Al Cohn, Oscar Pettiford, Clark Terry, Oliver Nelson, and Hank Jones. Only diehard Connor fans will be disappointed by the anthology’s shortcomings. The song selection favors familiar material (“Misty,” “Summertime,” “I Got Rhythm”) and obscures the singer’s knack for discovering such offbeat, challenging compositions as “Round About,” “Thursday’s Child,” and “Fancy Free.” Ten of the tracks unnecessarily duplicate selections already available on American CD reissues. The fatuousness of producer Joel Dorn’s Dick-and-Jane preface (“Chris Connor’s cool. And the way she sings is cool. That makes her double cool.”) is matched by Will Friedwald’s inane liner-note essay, which tells us much more than we need to know about himself, but next to nothing insightful about Connor’s art.

In 1962, Connor unwisely took her manager’s advice and left Atlantic for FM, a company that folded just as her second album was about to be released. Then came the rock youthquake of the mid-’60s, which consigned the careers of most jazz-oriented vocalists to a limbo from which they did not emerge until the early ’80s. During this period, Connor released several one-shot recordings for independent labels and came to terms with a drinking problem—an occupational hazard of nightclub performers. A brace of critically acclaimed ’80s Contemporary CDs—Classic and New Again— revitalized her career and led to new engagements here and abroad.

Connor is now a technically more assured musician than in her heyday. Her intonation is more precise and, if anything, she swings harder than ever before. But her singing has become more conservative. These days, her repertoire consists of road-tested standards (“The Thrill Is Gone,” “It Might as Well Be Spring”), and she sticks closer to the written melody, curbing her erstwhile penchant for reckless improvisation.

“I don’t experiment as much,” Connor remarked when I interviewed her in 1995, “although my voice has gotten deeper and stronger. When you’re young, you overplay as a musician and you oversing as a singer because you’re trying all these ideas. I was throwing in everything but the kitchen sink. I’ve eliminated a great deal of the things I used to do. The simpler it is, the better it works for me.” CP

Chris Connor appears at the Mary Lou Williams Women in Jazz Festival on Saturday, May 8, at 7 p.m. in the Kennedy Center’s Terrace Theater.