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“Kay did a superb job with our songs,” recalled Engvick. “They were so beautifully rehearsed and laid out. It was just really exciting to see Kay do those songs in her own inimitable way.”

The only missing ingredient was money. In search of some traction, Kay pressed her husband to add one of the show’s tunes, “Lullaby,” to his band’s repertoire. Revisionists at heart, Kay and Jack could not help but play around with the arrangement and, in collaboration with Wilder and Engvick, they modified the lyrics and renamed the song “City Night.” Taking it to the next level, Jack adopted “City Night” as his orchestra’s theme song and recorded it for Vocalion Records.

Unfortunately, Jenney’s support was not enough to help
Ladies and Gents
; the money just never came together. “It was a little abstract,” Engvick lamented. “Maybe too abstract. The songs were pretty good, though, and if Kay Thompson had gotten to do them on Broadway, we really would have had something.”

A few years down the road, in the summer of ’42, Wilder and Engvick approached Kay again, this time to star with Jimmy Durante in an entirely new musical,
Sweet Danger
(aka
Brace Yourself, Brother
), a frothy mystery-comedy aimed straight at the masses. “The story revolves around a bevy of beautiful models,” read an account in
The New York Times
, “who go to the home of a society matron to display some costumes and there become involved in a spy plot.” But alas, once again, the financing never materialized.

O
n August 21, 1939,
a more musically focused
Tune-Up Time
resumed broadcasting on Monday nights with singing heartthrob Tony Martin replacing Walter O’Keefe as host. Kay had known Tony since 1932, when they
were wannabes with Tom Coakley’s band. Since then, Tony had become a star in movies and radio, bolstered considerably by his marriage to Alice Faye, which was all the rage in fan magazines. In stark contrast, Thompson had only achieved recognition in radio and had not yet mastered the art of celebrity. Her emotions were mixed about Tony; though she was intensely jealous of his success, she liked him and seemed to realize that riding his coattails might not be such a bad thing.

Ratings for
Tune-Up Time
started off big until
The Adventures of Sherlock Holmes
(with Basil Rathbone and Nigel Bruce) was launched at the same time on NBC, becoming as much of a threat as Crosby had been on Thursdays.

As if that weren’t enough, Tony Martin was suddenly hired by producer Irving Starr to top-line Columbia Pictures’
Music in My Heart
opposite the young Rita Hayworth. Much as
Hit Parade
had moved to Hollywood for Fred Astaire,
Tune-Up Time
now had to relocate itself in Hollywood for the five-week production schedule.

In exchange, Columbia Pictures agreed to plug
Tune-Up Time
in the movie itself. It made perfect sense because Tony’s fictional character, Robert Gregory, was the star of a radio show that now, in a case of art imitating life, would be called
Tune-Up Time.
Kostelanetz would play himself as the conductor and it was assumed that Thompson and her chorus would appear as well.

To curb costs, Kosty would use local musicians from the orchestra at KNX, the new CBS affiliate. However, there was no Los Angeles equivalent of the Rhythm Singers, so Kay had to assemble a new choir from scratch. During the first Hollywood broadcast of
Tune-Up Time
on October 2, Kay performed two hot new Arlen-Harburg songs, “Ding-Dong, the Witch Is Dead” (with her West Coast Rhythm Singers) and “Over the Rainbow” (a duet with Tony)—both, of course, from
The Wizard of Oz,
which had just been released in August.

Meanwhile, prerecordings got under way for
Music in My Heart
. According to Tony Martin, Thompson was involved as an uncredited vocal arranger and choral director on some of the numbers. These most likely included “Punchinello,” sung by Martin and the Brian Sisters, which was loaded with Thompsonian tempo shifts and harmonics. Kay also likely provided the choral arrangement and direction of the large mixed choir for “I’ve Got Music in My Heart,” sung by Martin, which was subsequently performed on the November 6 edition of
Tune-Up Time
by Tony and Kay’s Rhythm Singers.

However, when Kay realized she would only get to sing one duet with Tony in the movie, and that the rest of her screen time would be spent in the background directing the choir, she balked. If she couldn’t “look like a star in this movie,” she would rather not do it. And so, she didn’t.

“If you have no confidence in yourself,” Kay told a reporter, “who’s to have confidence in you? You’ve got to carry your nerve in your pocketbook, along with your powder-puff and make-up. Otherwise you’ll never get anywhere.”

A tad less nerve might have gotten her farther. The executives at Ethyl Gasoline felt Kay had blown a huge opportunity to promote their show, and despite Bill Spier’s valiant defense of her point of view, they decided to let her go when her contract expired at the end of the year.

Her artistry was never in question. Reviewing the October 30 installment of
Tune-Up Time, Variety
reported, “Musical ingredients were topflight Monday, especially Kay Thompson’s whammo version of ‘I Didn’t Know What Time It Was’ from [George] Abbott’s
Too Many Girls.

And in November, it was reported that Cole Porter was so impressed by Thompson’s rip-roaring version of “Katie Went to Haiti” from his upcoming Broadway musical,
Du Barry Was a Lady,
he adopted certain riffs during the last week of tryouts.

Nonetheless, her days were numbered. “Kay Thompson and her choir depart from the show after the broadcast of December 25,” a columnist lamented in
Radio Guide.
“An unwelcome Xmas present, I’d say.”

Even more depressing was the situation with her husband. A slave to his alcohol addiction, Jack had become frightfully emaciated, his weight falling below 140 pounds. The robust five-eleven buck who married Kay in 1937 had aged twenty years in less than three.

“He wasn’t the poster boy for marriage,” recalled Gary Stevens, Kay’s publicist around that time. “And Kay wasn’t the marrying type really. They were hardly ever together. She was running around with her entourage, song pluggers and singers. He used to hang out at Charlie’s Tavern with a lot of musicians. His big pal was Bunny Berigan, who was an unforgivable drinker. Jack seemed to be just involved with his drinking and playing his instrument, working with the guys.”

The most damning account, though, was the claim by Jenney’s band boy that various items of jewelry were being “hocked to supply booze money.” If that jewelry belonged to Kay, the betrayal would have been irreparable.

“Hughie McFarland was Jack Jenney’s band boy and great friend,” Robert Wagner recalled. “They were drunks together. They hung out together. Hughie told me that on at least one occasion, Kay had thrown Jack out of her apartment.”

“As far as I’m concerned, a less likely couple never married,” Alec Wilder wrote in an unpublished memoir. “They both loved swinging music and were talented musicians but there, outside of probable sexual attraction, the similarity
of taste stopped. He loved to drink and she went with him to the bars, but I never remember seeing her the worse for it.”

Walter Winchell was onto something when he wrote in his October 12, 1939, column: “Kay Thompson, the thrush, and her groom are talking Renonsense.” As in Reno, Nevada, the land of the quickie divorce.

The December 1, 1939, issue of
Radio Guide
reported, “They say all is not well between Kay Thompson and her bandleader husband, Jack Jenney, and a visit to the divorce courts is on their schedule.”

At the same time, Kay’s relationship with Bill Spier was becoming more serious. Spier’s daughter, Greta, recalled that her parents’ marriage was dissolving during that period. “Once my sister, Margaret, was born in September of ’39, their marriage didn’t last much after that.”

The romance between Thompson and Spier intensified in October when they spent five weeks at the same hotel in Hollywood for
Tune-Up Time
. “Kay and Bill were very friendly,” confirmed Tony Martin, “and we could see it developing.”

In the autumn of her life, Kay admitted to Liza Minnelli that, although Jack’s alcohol consumption was crippling their marriage, it was his womanizing that broke the camel’s back. In a 2008 interview for this book, Liza said, “Kay told me that, in those days, filing for divorce wasn’t easy. There had to be a specific reason and you had to prove it.”

“Will these do?” Kay deadpanned to the police as she dangled a pair of women’s panties that did not belong to her. To Thompson’s dismay, however, harder evidence was required.

To bolster her case, Thompson had to engage a private detective to photograph Jenney in the act—an indignity that Kay found “highly unattractive.”

The divorce petition was filed in late 1939, and Kay and Jack went their separate ways. Jack wasn’t just losing a wife; in March 1940, MCA dropped him as a client and his orchestra bookings dried up. Unable to keep his ensemble afloat, Jack turned up a few months later blowing trombone for Artie Shaw and His Orchestra. That same year, columnist Dorothy Kilgallen scooped, “Jack Jenney, the bandleader, will marry Bonnie Lake, Ann Sothern’s sister, as soon as his divorce from Kay Thompson, the singer, is sealed.”

On October 10, 1940, Jack and Bonnie made it official in a quickie Reno ceremony. Shortly thereafter, his new bride joined Shaw’s band as a vocalist.

“Jack was a helluva musician,” recalled trombonist Ray Conniff, who sat next to Jack in Shaw’s band. “But gosh, he just ruined his life with that booze. Kay used to try to help him the best she could. Artie did. We
all
did. But he couldn’t control it.”

W
hen things were not
going well, Kay was drawn to the light—but not in the heavenly sense. Her idea of spiritual healing was being blinded by a spotlight while performing in front of an adoring crowd. Having just lost her father, her husband, her youth (she’d just hit the big 3-0), and the best radio job she ever had, she needed a round of applause. So, she created an act and, on February 6, 1940, she headlined the Famous Door nightclub on Swing Street.

“She did a twenty-five-minute set with a pianist and a bass player,” recalled her publicist Gary Stevens. “She did some of the show standing up and occasionally she just slid in at the piano and played a few numbers on her own. Kay had a very sophisticated act, far and above what Fifty-second Street required—interpretations of songs, special material, she did the arrangements, she wrote special lyrics, she did everything. She was writing it herself and changing it every three or four days—adding stuff, taking it out.”

Kay performed her set twice a night at eleven and twelve-thirty. Incredibly, she also ran through a condensed eight-minute version of the act four times daily at the Loew’s State in Times Square, between showings of
Balalaika,
with her last performance ending around nine-thirty. Unlike the hipster-cool atmosphere of an intimate jazz club, the Loew’s State was strictly old-school vaudeville, with square-jawed action star Chester Morris among the acts.

“Kay Thompson comes into vaude with quite a national radio rep,” read the review in
Variety,
“but the latter has been built up via her singing in front of a choral group. On the stage here, however, she’s appearing solo and the chorus is missed by the audience.”

Like it or not, Kay’s choir had become her claim to fame as well as her ball and chain. The
Variety
critic conceded that “as a singer and in stage deportment in front of a mike, Miss Thompson is A-1,” but found fault in her decision to open with a blues number, “The Answer Is Love,” which was deemed “much too slow to tee-off.” Heeding the advice, Kay switched to a jazz-hot swing makeover of “How Deep Is the Ocean” that got the house rocking and became one of her most beloved arrangements.

“Kay was just using those engagements as a test for herself,” Stevens concluded. “She wanted to know if she was serious about doing a nightclub act. In the end she wasn’t too happy with how it turned out. She just said, ‘Oh, the hell with it.’ ”

In search of a new direction, she nixed radio appearances and visited friends in Hollywood, hoping another movie role might come her way. When
it didn’t, she earned money by coaching singers and freelancing as a vocal arranger. According to pianist Skitch Henderson, Kay collaborated with Conrad “Connie” Salinger on the arrangements for a couple of Judy Garland numbers in
Ziegfeld Girl
and
Andy Hardy Meets Debutante
—Thompson’s first brush with MGM.

“Kay, of course, was a big friend of Connie’s because they worked together a lot,” recalled orchestrator Alexander Courage in an interview with Leonard Maltin. “They were known for all those long impossible endings they put on all those numbers at MGM that went on forever. André [Previn] and I used to imitate them on the road when we were driving along.”

For
Andy Hardy Meets Debutante
, Kay and Connie arranged “Buds Won’t Bud,” a song originally written for
Hooray for What!
that, like Thompson, had been axed during the Boston tryout. By the time
Andy Hardy Meets Debutante
hit theaters, however, “Buds Won’t Bud” had died on the vine again, left on the cutting room floor. The third try was the charm when Ethel Waters sang “Buds Won’t Bud” in
Cairo
(MGM, 1942).

“That was the mafia, Connie and Kay,” Skitch Henderson fondly recalled. “And they joked that our conductor, Georgie Stoll, knew
nothing
, which was the first time I’d heard anybody put down conductors.”

Still, Thompson was feeling restless and unfulfilled. Shortly thereafter, she returned to New York to form a new backup chorus that she named the Okays; together, they recorded several songs for Viking Records, including a cover version of “Dolores,” the Oscar-nominated song from
Las Vegas Nights
. The results, however, seemed uninspired and sales were limp.

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