In the 1940s, both Judy Garland and Frank Sinatra were major stars of Hollywood’s Golden Age, known for their exceptional singing and charisma. The two performed together on Sinatra’s radio show multiple times, including an episode on May 24, 1944. These collaborations were popular morale boosters during World War II, allowing Americans to escape the realities of war through their music. They were also part of the “Committee for the First Amendment” in 1947, which opposed the Hollywood blacklist.
They were romantically involved for a short time starting in 1949. This took place while Garland was married to director Vincente Minnelli and after Sinatra had separated from his wife, Ava Gardner. The couple would have a second, brief romantic relationship later in 1955 during a separation from her husband, Sidney Luft.
Sinatra was known for being very protective of Garland and was a constant source of support throughout her life. They remained close friends until her death in 1969.
According to vintagehollywoodstars, Sinatra paid for Garland’s funeral and interment, which was approximately $37,500 because Garland was deeply in debt at the time of her death. His offer to pay was initially turned down by Garland’s daughter, Liza Minnelli, who felt she could raise the funds herself for a simpler burial, though she was ultimately unable to do so.
In 2016, a four-page love letter from Judy to Frank, written after a secret Hamptons meeting, was auctioned and sold for $5,897. Part of the letter read: “You said today that you’d been negligent. But darling—that’s so unimportant compared to the great amount of happiness you’ve given me. I shall not forget the hours we’ve spent together—ever!”


































