![]() Pearl Bailey’s whirlwind love affair seemed like a dream come true- but it was more of a horror story. Bailey already dealt with a lot of bad behavior from men while she was on stage, and she wasn’t about to put up with it at home. The young couple didn’t waste any time in making it official-but they didn’t exactly settle right down. Bailey mostly brushed off the miners’ advances, but on her journey across Pennsylvania’s sooty, ashy camp towns, she met a drummer who caught her eye. Pearl Bailey was living in a man’s world-and as a stunning young woman, she attracted a lot of attention. But in her personal life, she could still be quite naïve… 8. While she was initially taken aback by their aggressive and occasionally creepy behavior, she soon learned to hold her own. These were very different from the Philly nightclubs- and young Pearl found out about their dark side the hard way. Sometimes, her nights would end with her in the middle of a violent brawl, with bottles flying by her face. Her Shows Were Chaoticīailey’s first long-term contract was to perform in the “coal circuit.” The coal circuit was Pennsylvania’s coal towns, which housed a lot of Black miners. Pearl couldn’t afford to be picky, and unfortunately, this led to some unsavory gigs. Most weeks, she made just enough for rent and to feed herself-with not a penny leftover. ![]() There was no looking back after that she started singing and dancing on the vaudeville circuit and traveled to New York with them too.Īlthough she was living her dream, it didn’t mean that Bailey was comfortable. She decided she wanted to be a singer and won another amateur contest in the Apollo Theater. This interlude at the club showed Bailey that she didn’t have to go back to cleaning houses to make a living. There was a lesson learned…and considering how seedy the performing world at the time, she’d need all the street smarts she could muster. Pearl wasn’t only jobless-they’d never paid her. Despite her triumph, she was in for a brutal disappointment. After two weeks of jaw-dropping performances, the club suddenly went bust. Not only did she win the competition that night, but the club also signed her for a full two weeks of performances. When Pearl Bailey performed the song “Poor Butterfly,” she left the audience stunned. When Bailey entered an amateur competition, she surprised not only herself-but the audience too. And hey, after all, Pearl had that great sense of rhythm she’d learned at church. Her brother Willie had actually found one-he’d been performing as a tap dancer on bills with more established artists. Exhausted from work and school, she knew there had to be a better way. She Was Overworked And UnderpaidĪt just 15, Pearl Bailey was out there working as a cleaner for rich white families in well-to-do areas of Philadelphia. ![]() But unlike most teens, she wasn’t exactly out there delivering papers… 4. The family struggled-and each kid had to help out in their own way, including a teenaged Pearl. While Pearl’s mom remarried, it was no happily ever after. Not only did she pack up the kids and leave her husband, but she also took them all the way to Philadelphia. 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. Sunday was the biggest day of the week in the Bailey family-but it wasn’t because of the weekly service. But although Sundays were filled with joy at the church, the same could not be said of her home life. Not only did Pearl find a sense of rhythm and appreciation for music…she also realized that it could be quite lucrative. With all that fun came the enthusiastic emptying of pockets. 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. There, her father led one of the largest congregations in the city. The Bailey family moved to Washington, D.C. Well, as they and the world would come to learn-Pearl Bailey was always full of surprises. And so attached were they to that moniker that they called Bailey “Dickie” for most of her childhood. So certain, in fact, that they’d fixed on a name: Dick. They’d been certain they were having a boy. Pearl May Bailey’s birth in 1918, in Newport News, Virginia, came as a surprise to her Pentecostal preacher dad and homemaker mom.
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