You may (or may not) have heard that legendary jazz singer Billie Holiday once babysat for comedian Billy Crystal when he was a child. It’s one of those things that pops up online from time to time, and nobody really questions it. But is there any truth to this story? Even after some basic research, it becomes pretty clear that Holiday was already famous by the time Crystal was born, so what would she have been doing babysitting at that point in her career? Let’s take a closer look at the facts.
In his 2005 memoir, 700 Sundays, Crystal mentions that he did, in fact, know Holiday as a child. His connection to the singer was through his uncle, Milt Gabler, the founder of Commodore Records, who produced Holiday’s songs as well as those of artists like Nat King Cole and Ella Fitzgerald. It was Gabler who recorded “Strange Fruit” with Holiday, a controversial song about lynchings in the South that became the highest-selling record of her career. TIME magazine selected it as the song of the century in 1999.
Holiday used to call Crystal “Mister Billy,” and he called her “Miss Billie.” She was one of many musicians who regularly visited Crystal’s family home. One time, when Crystal’s father was producing a concert for Holiday in New York, they got to watch her rehearse. It was on that day, according to Crystal, that Holiday said the life-changing words to him, “Hey, Mister Billy, let’s go to the movies.”
The two then walked to the theater next door and caught a screening of the 1953 Western Shane, starring Alan Ladd and Jack Palance. It was the first movie Crystal had ever seen. By the time the credits were rolling, he was seated upon Holiday’s lap with tears in his eyes. He was so moved by the performance of the child actor in the film, Brandon deWilde, that he wanted to be up on the screen himself.
We’re not sure that this can necessarily be considered babysitting, but Crystal did actually spend time with Holiday during his childhood, so that part is true. Holiday died just a few years after that in 1959, when Crystal was only 11 years old. Crystal later put together a compilation album called Billy Remembers Billie, featuring his favorite songs from the late singer.
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