John F. Kennedy Had This Hollywood Legend Serenade Him to Sleep Every Time They Called

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While most people know about John F. Kennedy’s alleged affairs with Hollywood Legends like Marilyn Monroe, Audrey Hepburn, and even Marlene Dietrich, there’s one relationship with a legend most don’t know about. Now, before we dive in, we should let you know that this relationship wasn’t a romantic or sexual one (as far as we know in 2023), but it was a rather unexpected friendship.

It turns out Judy Garland was one of Kennedy’s closest friends later in life. And at the end of their calls, she would sing the iconic song “Over the Rainbow” every single time, per his request.

In the 1975 book Judy by Gerald Frank, her eldest daughter Liza Minnelli, talked about how in the early 1960s, she would call Kennedy after work. Minnelli says her mother would say something like “What a week. I think I’ll call Jack.” Minnelli said she often heard her mother say, “Oh, no, again? Do you really want me to do that again? All right…”

And then she’d sing the end of “Over the Rainbow” for Kennedy. (This was later confirmed in Garland’s third husband Sid Luft’s posthumously released memoir entitled Judy and I!)

Now, Garland and Kennedy’s friendship goes way back, to when he was a junior Senator. Per People, they met through his younger sister Patricia and her husband Peter Lawford. They became fast friends, and Garland supported his political aspirations.

In fact, after his assassination, Garland honored him by singing “The Battle Hymn of the Republic” on The Judy Garland Show.

Before you go, click here to see the biggest presidential scandals in US History.