Writing for Turner Classic Movies, biographer Jonathan Riggs observed that Garland had a tendency to imbue her vocals with a paradoxical combination of "fragility and resilience" that eventually became a signature trademark of hers. Louis Bayard of The Washington Post described Garland's voice as "throbbing", believing it to be capable of "connect[ing] with [audiences] in a way no other voice does". Bayard also believes that listeners "find it hard to disentwine the sorrow in her voice from the sorrow that dogged her life", while Dowlin argued that, "Listening to Judy sing ... makes me forget all of the angst and suffering she must have endured." The New York Times obituarist in 1969 observed that Garland, whether intentionally or not, "brought with her ... all the well-publicized phantoms of her emotional breakdown, her career collapses and comebacks" on stage during later performances. The same writer said that Garland's voice changed and lost some of its quality as she aged, although she retained much of her personality. Contributing to the Irish Independent, Julia Molony observed Garland's voice, although "still rich with emotion", had finally begun to "creak with the weight of years of disappointment and hard-living" by the time she performed at Carnegie Hall in 1961. Similarly, the live record's entry in the Library of Congress wrote that "while her voice was still strong, it had also gained a bit of heft and a bit of wear"; author Cary O'Dell believes Garland's rasp and "occasional quiver" only "upped the emotional quotient of many of her numbers", particularly on her signature songs "Over the Rainbow" and "The Man That Got Away". Garland stated that she always felt most safe and at home while performing onstage, regardless of the condition of her voice. Her musical talent has been commended by her peers; opera singer Maria Callas once said that Garland possessed "the most superb voice she had ever heard", while singer and actor Bing Crosby said that "no other singer could be compared to her" when Garland was rested.
In November 1959, Garland was hospitalized after she was diagnosed with acute hepatitis. Over the next few weeks, several quarts of fluid were drained from her body until she was released from the hospital in January 1960, still in a weak condition. She was told by doctors that she likely had five years, or less, to live, and that, even if she did survive, she would be a semi-invalid and would never sing again. She initially felt "greatly relieved" at the diagnosis. "The pressure was off me for the first time in my life." However, she recovered over the next several months, and in August of that year, returned to the stage of the Palladium. She felt so warmly embraced by the British that she announced her intention to move permanently to England.
More InfoUpon Garland's death, despite having earned millions during her career, her estate came to US$40,000 (equivalent to $278,875 in 2019). Years of mismanagement of her financial affairs by her representatives and staff along with her generosity toward her family and various causes resulted in her poor financial situation at the end of her life. In her last will, signed and sealed in early 1961, Garland made many generous bequests which could not be fulfilled because her estate had been in debt for many years. Her daughter, Liza Minnelli, worked to pay off her mother's debts with the help of family friend Frank Sinatra.In 1978, a selection of Garland's personal items were auctioned off by her ex-husband Sidney Luft with the support of their daughter Lorna and their son Joe. Almost 500 items, ranging from copper cookware to musical arrangements, were offered for sale. The auction raised US$250,000 (equivalent to $979,974 in 2019) for her heirs.
More InfoIn 1961, Garland and CBS settled their contract disputes with the help of her new agent, Freddie Fields, and negotiated a new round of specials. The first, titled The Judy Garland Show, aired on February 25, 1962 and featured guests Frank Sinatra and Dean Martin. Following this success, CBS made a $24 million offer to her for a weekly television series of her own, also to be called The Judy Garland Show, which was deemed at the time in the press to be "the biggest talent deal in TV history". Although she had said as early as 1955 that she would never do a weekly television series, in the early 1960s, she was in a financially precarious situation. She was several hundred thousand dollars in debt to the Internal Revenue Service, having failed to pay taxes in 1951 and 1952, and the failure of A Star is Born meant that she received nothing from that investment.
More InfoGarland was then cast in the film adaptation of Annie Get Your Gun in the title role of Annie Oakley. She was nervous at the prospect of taking on a role strongly identified with Ethel Merman, anxious about appearing in an unglamorous part after breaking from juvenile parts for several years, and disturbed by her treatment at the hands of director Busby Berkeley. Berkeley was staging all the musical numbers, and was severe with Garland's lack of effort, attitude, and enthusiasm. She complained to Mayer, trying to have Berkeley fired from the feature. She began arriving late to the set and sometimes failed to appear. At this time, she was also undergoing electroshock therapy for depression. She was fired from the picture on May 10, 1949, and was replaced by Betty Hutton, who stepped in to perform all the musical routines as staged by Berkeley.
More InfoGarland was left in a desperate situation which saw her sell her Brentwood home at a price far below its value. She was then cast in February 1967 for the role of Helen Lawson in Valley of the Dolls by 20th Century Fox. According to co-star Patty Duke, Garland was treated poorly by director Mark Robson on the set of Valley of the Dolls and was primarily hired so as to augment publicity for the film. After Garland's dismissal from the film, author Jacqueline Susann said in the 1967 television documentary Jacqueline Susann and the Valley of the Dolls, "I think Judy will always come back. She kids about making a lot of comebacks, but I think Judy has a kind of a thing where she has to get to the bottom of the rope and things have to get very, very rough for her. Then with an amazing inner strength that only comes of a certain genius, she comes back bigger than ever".
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