In the late 1930s, jazz clarinetist Artie Shaw became one of America’s most popular big band leaders — and a much desired man. “People ask what these women saw in me,” the musician said. “It’s the music; it’s standing up there under the lights. A lot of women just flip.”

Teenaged Judy Garland fell under Artie’s spell on a trip to New York. Although their romance was doomed from the start, their friendship became one of the most genuine of Artie’s life — and lasted longer than his marriage to Judy’s friend and rival, Lana Turner. Judy and Artie met in 1937 when she saw his band perform.

“She loved his sound and went up afterwards and introduced herself,” says Gerald Clarke, author of Get Happy: The Life of Judy Garland. He adds that it was likely that Artie knew who Judy was, although she wasn’t a big star yet. “He was impressed by the sophistication of her musical knowledge. Judy was very intelligent.”

Artie prized learning and had only entered the music business as a way to pay for college. He appreciated Judy’s keen mind, and they began seeing each other without her mother’s knowledge. “He taught her what books and novels to read,” her daughter Lorna Luft tells Closer. But Judy was only 16, and Artie was 12 years her senior and already twice-married.

“Artie described her as bubbly, full of fun, lively and intelligent,” says Clarke, who adds that the bandleader thought of Judy primarily as a younger sister. “He said they never did anything — although she tried. He would lean down to kiss her forehead when they said goodbye and Judy would turn up her lips.”

Meanwhile, when Artie met fellow MGM star Lana Turner on the set of 1939’s Dancing Co-Ed, sparks failed to fly. Lana said she found the musician aloof and boring. That changed after Judy confided to Lana about her crush on Artie.

Judy Garland Was ‘So Devastated’ When Lana Turner and Artie Shaw Eloped: ‘She Screamed'
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“Lana had a little mischievous quality,” says Clarke. She agreed to dinner with Artie to spite her commitment-adverse boyfriend, attorney Greg Bautzer. On their night out, the bandleader poured on the charm. “Artie would paint me a romantic dream with a white picket fence around it,” recalled Lana. “His eloquence stirred me.”

That night, Artie and Lana, then 19, eloped to Las Vegas. Actress Ann Rutherford, a friend, explained that Lana was a good girl. “She didn’t believe in sex before marriage, so if you wanted to [have sex with] Lana, you had to marry her,” she said.

The next day, Judy found out about their marriage in the newspaper. “She screamed, she was so devastated by it,” says Clarke. “She went to her room and banged her head against the wall.”

Judy may have gotten off easy. Lana filed for divorce just four months later citing Artie’s mental cruelty. “He literally flew into rages,” said Lana. Explains Clarke of the eight-times wed musician: “He was a very intelligent man, but he didn’t treat women well.” Artie and Judy would, however, remain friends. He was even present at her wedding to Vincente Minnelli in 1945.

“Everyone that my mother fell in love with was incredibly gifted,” says Lorna. “They always taught her things, and she loved to learn.”