Swinging Facts About Pearl Bailey, The Ambassador Of Love

Pearl Bailey was a tough woman to put in a box. Sure, she was a fantastic singer, but she was also a dancer, actor, “humorist,” humanitarian—and even with all that going on, she still had time for a scandal-filled personal life. When it comes to this legend, there’s a lot more than meets the eye.


1. She Was A Surprise

Pearl May Bailey’s birth in 1918, in Newport News, Virginia, came as a surprise to her Pentecostal preacher dad and homemaker mom. They’d been certain they were having a boy. So certain, in fact, that they’d fixed on a name: Dick.

And so attached were they to that moniker that they called Bailey “Dickie” for most of her childhood.

Well, as they and the world would come to learn—Pearl Bailey was always full of surprises.

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2. She Caught On Quick

The Bailey family moved to Washington, D.C. when Pearl was four. There, her father led one of the largest congregations in the city.

Pearl observed and joined in as the people around sang joyful gospel songs and danced exuberantly—but that wasn’t the only thing she noticed. With all that fun came the enthusiastic emptying of pockets.

Not only did Pearl find a sense of rhythm and appreciation for music…she also realized that it could be quite lucrative. But although Sundays were filled with joy at the church, the same could not be said of her home life.

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3. She Had To Chip In

Sunday was the biggest day of the week in the Bailey family—but it wasn’t because of the weekly service. Behind the scenes, her family was falling apart. Bailey’s parents fought like cats and dogs, and one week, Pearl’s mother decided she’d had enough. Not only did she pack up the kids and leave her husband, but she also took them all the way to Philadelphia.

While Pearl’s mom remarried, it was no happily ever after. The family struggled—and each kid had to help out in their own way, including a teenaged Pearl. But unlike most teens, she wasn’t exactly out there delivering papers…

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4. She Was Overworked And Underpaid

At just 15, Pearl Bailey was out there working as a cleaner for rich white families in well-to-do areas of Philadelphia. Exhausted from work and school, she knew there had to be a better way.

Her brother Willie had actually found one—he’d been performing as a tap dancer on bills with more established artists. And hey, after all, Pearl had that great sense of rhythm she’d learned at church.

When Bailey entered an amateur competition, she surprised not only herself—but the audience too.

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