One of the most talented singers to emerge from the swing era, Anita O’Day was a master at improvisation and an impressive jazz vocalist. Hard-swinging and hard-living, and often difficult to work with, O’Day made her mark during the 1940s with the bands of Gene Krupa and Stan Kenton before embarking on a solo career that took her into the 1990s. Though celebrated in the jazz world, her erratic nature and drug addiction kept her from ever achieving true success. She also refused to compromise and perform popular music, which limited her appeal with the general public.

A native of Chicago, O’Day was the product of an unstable home, with an alcoholic father who liked to gamble. She began using the surname O’Day in the mid-1930s while competing professionally in “endurance shows,” more commonly known today as dance marathons. Discovering that she could sing, she began working around Chicago in the late 1930s, spending most of 1939 in the Off-Beat Club, where she became a favorite of local musicians and began to attract national attention thanks to build-up by Down Beat magazine, whose editor, Carl Cons, owned the club. A botched tonsillectomy as a child had resulted in the loss of her uvula, and she developed a unique singing style to make up for the loss of vibrato in her voice.

O’Day got her first taste of band work in September 1940 with Raymond Scott, who had made his name performing eccentric compositions but had recently formed a dance band. Scott lost vocalist Nan Wynn while in Chicago and offered O’Day an audition. He was initially unhappy with her because she couldn’t sing in the key in which most of his arrangement were written, but after finally selecting a song he seemed satisfied and hired her. Scott was difficult to work with, however, and he expected his singers, and musicians, to perform his works exactly as written. He angrily fired O’Day after only three days when during a performance in Madison, Wisconsin, she forgot the lyrics to a new song he’d given her only hours before and had to improvise.

After leaving Scott, O’Day returned to Chicago, reluctant to sing again with a band until Gene Krupa convinced her to join his orchestra in February 1941, where she replaced Irene Daye. O’Day quickly made a name for herself with Krupa. Her dynamic stage presence and powerful voice graced many of the band’s best recordings. She often sang with trumpeter Roy Eldridge, a pairing that was a favorite of fans. Together they produced the song “Let Me Off Uptown,” which proved to be Krupa’s first major hit. O’Day typically wore suits on stage, eschewing the usual gown worn by most girl singers. She felt no need to accent her femininity, instead relying on her voice to sell her talents. As Krupa’s vocalist, she placed sixth in Billboard magazine’s 1942 college poll for best female band vocalist and fifth in the 1943 poll. She placed third in Down Beat’s poll in both 1941 and 1942.

O’Day left Krupa at the end of the group’s December 29, 1942, show at the Hollywood Palladium. At the time she indicated that she simply wanted a break. “I’m just tired and want to take a rest,” was the only statement she made on her departure, though some later sources report ill-feelings between her and Eldridge as the cause. During the break, she married pro golfer Carl Hoff on January 18, 1943. Hoff, then in the service, later became O’Day’s business manager.

O’Day returned to Krupa’s band three weeks after her departure, appearing with them at the Hotel Sherman in Chicago, but didn’t stay long, temporarily retiring again and returning to the West Coast, where her husband was stationed. She returned to activity as a solo artist in May 1943, booking herself into Charlie Foy’s Supper Club in Hollywood. She then landed a job with Woody Herman in June, replacing Carolyn Grey, who had left suddenly. She quit Herman the following month, however, not wanting to follow the band to the East Coast.

After leaving Herman, she opened as a single in July at Slapsie Maxie’s in San Francisco and then returned to Charlie Foy’s. She soon found that staying in California limited her options, though, and she signed with a booking agency in September, going out on the road. Reviews during this time reveal her as awkward and unsure how to act or dress as a single. On April 28, 1944, she joined Stan Kenton’s progressive jazz outfit, replacing Dolly Mitchell.

With Kenton, O’Day again proved wildly popular with both critics and audiences, placing first in Down Beat’s poll for both 1944 and 1945, fifth in Billboard’s 1945 poll, ninth in 1946 and second in 1947. She made several recordings with Kenton’s band, including their first hit song, “And Her Tears Flowed Like Wine.” Leaving Kenton in February 1945, she had no definite plans for the future other than to return to California, taking another vacation from work. In June, she recorded on the new Gem label backed by the Abby Brown orchestra, the house band at Charlie Foy’s. O’Day, however, forgot that she was still under exclusive contract with Capitol Records, Kenton’s label, and Capitol threatened legal action. The matter was finally settled, and the recordings were allowed to be released on Gem. She also gained permission to record for Krupa on Columbia, whom she rejoined in July.

Back with Krupa, she again formed one of the most popular singing teams in the country, this time with male vocalist Buddy Stewart. In December, however, both she and Stewart announced their intentions to leave. O’Day’s departure came unexpectedly in January 1946 when she pulled out midway during the band’s run at the Hollywood Palladium and only thirty minutes before a coast-to-coast broadcast, saying she felt ill. She never returned. Krupa had to scramble and find a vocalist to fill in, which happened to be the singer for the intermission band, the very same Carolyn Grey whom O’Day had replaced after Grey’s sudden departure from Herman three years earlier.

O’Day remained inactive for several months after leaving Krupa. Reports in June 1946 suggested that she would join Les Brown, but she did not return to singing until September, when she launched a solo career again, going back into the clubs. A deal was also signed for her to record four sides with Lionel Hampton on the Decca and Hamptone labels. In early 1947, O’Day and Hoff took over operation of the Swanee Inn on La Brea Avenue on a percentage deal. They had been attempting to open a club on the Sunset Strip but had run into building difficulties.

On March 21, 1947, police arrested O’Day and Hoff at their North Hollywood home on charges of marijuana possession. O’Day allowed police into the house, despite the fact that they had no search warrant, and officers found a bag of weed and rolling papers in a drawer. The couple pleaded not guilty and were booked and released under a $1,000 bond each. The arrests came during a time when local authorities were waging a campaign against drug use in the music world and caused a fair amount of consternation in the business, especially when Hoff was initially identified in the New York Daily News as the bandleader of the same name.[4] O’Day denied reports in the local press that she had said she’d known of the marijuana’s presence but didn’t use it. A preliminary hearing was set for April 4.

At the time, O’Day was appearing at Bocage, a Hollywood night club, backed by the Barney Kessel Trio. The arrest happened at around five in the afternoon, and once released on bail she immediately made her way to Bocage to give her performance. The club was shut down two days later due to an unrelated labor dispute. O’Day continued to travel and perform while awaiting trial.

O’Day also filed for divorce against Hoff. The singer insisted it had nothing to do with their arrest. “Just one of those things,” she told reporters. “Sometimes marriages just don’t work out.” Rumors of the divorce had begun during the couple’s preliminary hearing. Arresting officers had testified that Hoff and O’Day had told them they were separated or were on the verge of separation. Hoff indicated that divorce proceedings had already been started. The divorce suit was later dismissed, and the couple remained married.

Trial began on June 4. O’Day was represented by Earl Everett, who had previously represented Benny Goodman bassist Harry Babison for the same charge. Babison’s case had been dismissed due to lack of evidence before ever going to trial. O’Day and Hoff had no such luck. They were sentenced on August 11 to 90 days in jail, the judge refusing to believe their story that musicians who had been involved in a jam session at the house had left the items in the drawer without their knowledge. O’Day and Hoff claimed that they stayed infrequently at the home, living for the most part downtown and allowing friends to used their house when they weren’t there. An unflattering picture of the pair looking like deer caught in headlights was published in newspapers across the nation at the time of the sentencing.

O’Day was freed from jail after two days on $5,000 bond pending appeal. The appeal was denied, and O’Day spent time in the county jail. On October 21, she began a four-week engagement at the Red Feather in Hollywood. On opening night, a “rasp-voiced chick” in the audience began heckling her, interrupting her constantly. Staff did nothing to stop the heckler, and finally O’Day, having enough, put the woman down, something which was frowned on at the time. Artists working in establishments where liquor was served were expected to ignore drunks and hecklers. Red Feather management tried to fire O’Day on the spot, but O’Day’s union, the American Guild of Variety Artists, stepped in and reminded them that they could only give a warning on a first offense. Nevertheless, relations between O’Day and management became strained, and she left after only three weeks.

O’Day struggled as a solo artist. While she sold out clubs, she wasn’t happy working in small environments, complaining that she felt cramped. She preferred a larger stage, with bright lights and a full orchestra. Her performances were much more subdued in the confines of a night club, and audiences often reacted coolly.

After having trouble with instrumental backing in late 1948, O’Day formed her own six-piece band, and in mid-1949, she took up a long residence in Chicago’s Hi-Note club, back by Max Miller’s trio. She recorded sporadically in the late 1940s. In 1947, she signed with the Signature label, turning down an offer from Victor in late 1948 to stick with the smaller diskery. In 1949, she placed tenth in the category of all-around female vocalist in Billboard’s annual college poll and, oddly, fourth in the category of most promising new female vocalist.

She continued to struggle during the early 1950s. She signed with the London label in 1950 before moving to Mercury in 1952, where she recorded as part of Norman Granz’s jazz series. When Granz’s deal with Mercury expired in 1953, he began issuing O’Day’s recordings on the Clef and Norgran labels, both of which he owned.

O’Day and Hoff again filed for divorce in 1951, this time in Illinois. The suit was dismissed, but Hoff filed again in 1952 in his native Waukesha, Wisconsin, where he was then living, charging O’Day with desertion. The divorce was granted on June 23. Hoff stated that O’Day had left him “on or about” February 16, 1950. O’Day didn’t contest the suit or appear in court. Court documents listed her as living at the Croyden hotel in Chicago but the hotel said she wasn’t registered there. Hoff’s attorneys tracked her down to a Springfield, Illinois, night club, where she was both working and living.

O’Day was arrested again in Los Angeles for marijuana possession on October 15, 1952, after running a stop sign while driving. When police pulled her over they observed her throwing a “marijuana cigarette butt” from the car. Also arrested were two musicians in the car with her, Dennis Roche and Sheldon Robbin. O’Day insisted that she didn’t smoke marijuana and that friends had left it there. She later claimed it was a cigarette butt. She was freed on $200 bail with trial beginning in late January 1953. She was acquitted by a jury in February. In her autobiography, she admits that it had been marijuana.

A month later, on the night of March 14, 1953, O’Day was arrested yet again on narcotics charges. Police officers reportedly observed her inhaling pure heroin powder from a piece of tinfoil through the window of the ladies’ restroom at the rearof Club Samoa, a Long Beach night club. She then wrapped the tinfoil and placed it on top of a door frame. Roche, who was with her, was also arrested but no charges were issued against him. O’Day’s bail was initially set at $2,500 but reduced to $2,000 after she indicated she was short on funds.

O’Day’s lawyer, George Shibley, employed a variety of tactics and theatrics during her preliminary hearing, but his motion to dismiss the case on lack of competent evidence was denied. O’Day refused to take the stand on constitutional grounds. Arraignment was initially set for April 24, but Shibley asked for it to be postponed, saying that O’Day was “destitute” and had a singing engagement pending. He indicated that he’d been lending her money to live on. The judge moved the date to May 4. O’Day plead not guilty, and trial began on June 20.

Shibley’s defense revolved around arguments that Long Beach police were trying to entrap O’Day.[8] Shibley also contended that O’Day had not arrived at the night club until after the time police had observed her using heroin. The trial ended on July 31 in a hung jury, with one juror unconvinced of O’Day’s guilt. A new trial began on August 14.

O’Day had a new lawyer for the retrial, George Chula. Prosecutors unveiled a surprise witness who had previously seen O’Day sniffing heroin in the club’s restroom. Part of the prosecution’s case also rested on a ring worn by O’Day. Arresting officers had seen it on her hand when she was in the restroom. O’Day initially denied wearing it, but a local press photographer had taken a picture of her with the ring on at the time of her arrest. The jury found her guilty on August 25. O’Day’s remark upon the verdict was simply “I don’t know what I can say about it.”

Chula applied for O’Day to receive probation but did not submit the application in time for the September 28 hearing because his office had sent it through the mail, twice, with insufficient postage. An irate judge ordered a new hearing on October 23 but also ordered O’Day to jail until that time. Chula protested that the delay hadn’t been O’Day’s fault and vowed to ask for a new trial. O’Day replied, “It’s a dirty trick.” O’Day was ultimately sentenced to five months in the county jail with five years probation upon her release. She was credited with the time she’d spent in jail since her first hearing. A new trial was denied. For the rest of her life, O’Day denied her guilt and believed that she’d been framed.

O’Day was released from jail on February 25, 1954, a month early for good behavior and because she had a job waiting for her, She vowed to change her life and kick her drug habit. However, in August, she was yet again arrested for narcotics in Kansas City along with her drummer and close friend, John Poole, who was charged with illegal purchase and possession of codeine. Police subsequently released O’Day after Los Angeles County authorities stated they didn’t wish to start probation violation proceedings. Poole was turned over to federal authorities but charges were later dropped because officers had conducted an illegal search.

In late 1955, Granz assigned O’Day to his new pop-oriented Verve label, due to launch the following year. She was one of several jazz artists that Granz considered had commercial appeal. O’Day was in the recording studios for Verve in January. During those sessions, O’Day and Roy Eldridge joined Krupa’s band in recreating their old sound. It was her solo work, however, that received the most attention. Her initial LP for the label, Anita, the label’s very first album, proved extremely popular with critics and listeners. Soon she was in demand at major jazz festivals. She also began to work with other top performers and appear on television and in film. She placed third in Billboard’s 1960 poll for favorite female jazz singer.

Despite her successful comeback, however, O’Day still wasn’t happy. She was most unhappy with Verve, who stymied her requests to release singles. While her LPs sold well, she wasn’t being paid royalties from them. All her royalties were going to pay for her studio costs and to pay off costs of her older recordings which didn’t sell. She wanted a hit single, but Verve kept saying no to the songs she wanted to record. She asked to be released from her contract in 1957, which ran until 1960, but Verve refused. In 1958, Dorothy Kilgallen reported that O’Day was suing Granz because she hadn’t seen a royalty statement “in ages.” Granz claimed he was suing O’Day because she wasn’t living up to her contract.

O’Day’s addiction to heroin started to take its toll again in the early 1960s, and her career after 1963 became even more erratic. In 1960, Poole, falsely named in newspapers as her husband, was arrested and booked on suspicion of violating the state narcotics act.[12] She overdosed in 1967 and spent the next three years trying to kick her drug and alcohol addictions. Her career hit bottom. In 1969, she moved to Greenwich Village to get a fresh start, landing the occasional gig. After getting robbed and losing everything she had, she moved to Hawaii and then back to California.

O’Day made a slight comeback at the 1970 Berlin Jazz Festival, but her career continued to lag. In 1973, she was living in a three-dollar-a-night hotel room in North Hollywood, without a phone. Singing jobs were few and far between, her ability to find work not helped by her notoriously bad attitude. Her comeback trail started when jazz critic Leonard Feather did a story about her life. Soon after, she began receiving offers again, touring across the United States and Japan and singing at jazz festivals around the world.

O’Day recorded several more albums, some on her own label, Emily Records. In 1981, she released her autobiography, High Times, Hard Times. Though her voice began to deteriorate, she continued performing and recording throughout the 1980s and into the 1990s. Anita O’Day passed away in 2006, age 87.

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