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.
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.
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…
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.
5. They Screwed Her Over
When Pearl Bailey performed the song “Poor Butterfly,” she left the audience stunned. Not only did she win the competition that night, but the club also signed her for a full two weeks of performances. Despite her triumph, she was in for a brutal disappointment. After two weeks of jaw-dropping performances, the club suddenly went bust.
Pearl wasn’t only jobless—they’d never paid her. 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.
6. She Found Her Calling
This interlude at the club showed Bailey that she didn’t have to go back to cleaning houses to make a living. She decided she wanted to be a singer and won another amateur contest in the Apollo Theater. There was no looking back after that; she started singing and dancing on the vaudeville circuit and traveled to New York with them too.
Although she was living her dream, it didn’t mean that Bailey was comfortable. Most weeks, she made just enough for rent and to feed herself—with not a penny leftover. Pearl couldn’t afford to be picky, and unfortunately, this led to some unsavory gigs.
7. Her Shows Were Chaotic
Bailey’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. 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.
While she was initially taken aback by their aggressive and occasionally creepy behavior, she soon learned to hold her own. But in her personal life, she could still be quite naïve…
8. She Jumped In Headfirst
Pearl Bailey was living in a man’s world—and as a stunning young woman, she attracted a lot of attention. 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. The young couple didn’t waste any time in making it official—but they didn’t exactly settle right down. Quite the opposite, in fact.
9. She Went Her Own Way
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. Just as quickly as she’d fallen in love with the young drummer, she fell right out of it. Only 18 months after saying “I do,” Bailey and her husband decided to part ways and forget the whole debacle had ever happened.
As we’ll see, this “love ‘em and leave ‘em” attitude became a bit of a pattern…
10. She Made A Big Change
Not only was Pearl Bailey done with marriage, but she was also completely over the chaos and struggle of the coal circuit—so she made a drastic decision. Bailey made her way back to her childhood home of Washington, D.C., hoping for a bit of peace. But as anyone knows, when you make plans, fate has a way of laughing in your face.
Bailey had just found another nightclub gig when WWII broke out—leaving her without an audience. Well, what do you do when your audience suddenly deserts the clubs? You go out and track them down, of course.
11. She Faced A Bitter Truth
Bailey signed up to perform with the USO for enlisted men, and the tour took her all over the country—from Florida to Texas to Arizona and California. It seemed like a dream come true—but she soon made a disturbing realization. Even her status as a musician couldn’t protect her from the racial prejudice she faced on tour. She couldn’t stay at the same hotels as her white tourmates, or eat at the same restaurants. But sadly, segregation wasn’t the only thing she faced.
12. She Was The Victim Of Hate
One night, Pearl Bailey heard that Frank Sinatra would be performing at a New Jersey nightclub. Hoping to catch one of the legend’s songs, Bailey entered the club, expecting a night of fun. Instead, she became the victim of a brutal hate crime, as two white men attacked her when they saw her there. Bailey was hurt—and it left her with dire questions.
“How could a man hate someone he had never met before, just because he had a different skin color? What is he really afraid of?” Unfortunately, it was a question without a satisfying answer…
13. She Fell In Love Again
Bailey kept singing for USO throughout WWII—so we can’t really blame her for losing her heart to a soldier. Like her previous relationship, this too was a whirlwind romance that ended in marriage. Unfortunately, the similarities continued. They divorced in just a few months because he couldn’t adjust to regular life after the war ended.
Not one to dwell on setbacks, our girl Pearl threw herself in her career—and soon, the Universe rewarded her.
14. She Got Her Big Break
New York is a city where dreams come true—and Pearl Bailey was lucky enough to capture some of that magic. She arrived there in 1944 and quickly made a place for herself in two of the city’s best-known jazz clubs. Not only did she get to sing to a mixed audience, but also to the celebrities and bigwigs who frequented the place.
It was there that Columbia Records execs discovered her. Recognizing her talent, they jumped to sign her to her very first recording contract. After that, there was no looking back.
15. She Found Her Style
Singing in front of a New York audience was different from Bailey’s previous outings, but she quickly learned to loosen up on stage—and people loved her for it. Bailey also branched out from Columbia after a few songs, making hits for Coral and Roulette Records alike, including the scandalously-titled “For Adults Only.” Things were taking off for Bailey in ways she’d never imagined.
16. She Tried Something New
Bailey had a lot to do once she got to New York. She sang with jazz stars like Cab Calloway and Duke Ellington. She even got a little bit of redress for her horrible night in New Jersey when she met and collaborated with Frank Sinatra. The two became good friends afterward. On top of her work with music legends, Bailey also branched out into acting.
She made her Broadway debut in St. Louis Woman. She did so well that no one could have guessed it was her first time acting on stage. The woman was going places for sure—and she wasn’t afraid to speak her mind while she was on her way there either.
17. She Leveled Up
After her debut, Bailey acted in several other hit Broadway musicals like Arms and the Girl and House of Flowers, and then it was time to take the next step. Bailey got a part in the all-Black film Porgy and Bess. For any Hollywood newcomer, it was a dream come true—but Bailey quickly realized that she had a big problem. The film was taking a direction that she hadn’t predicted…and she wasn’t happy about it.
18. She Stood Her Ground
Most newcomers to film might be reticent to speak up on set. Not Pearl Bailey. The costume designer was the first one to realize Bailey wasn’t about to bite her tongue. Bailey refused to wear a bandana because it “smacked of Aunt Jemima,” and threw a fit when she saw the female choir singers wearing them too. And she didn’t stop there.
19. She Spoke Up Without Fear
Pearl Bailey knew that Porgy and Bess could be a ground-breaking film for Black people—and she wasn’t about to let any screenwriter or director ruin it. Bailey also demanded that the “undignified and unnatural Negro dialect” should be scrapped from the script. She thought the actors should talk naturally, “without the dems, doses and deses…We don’t talk like that. Maybe we did 50 years ago, but not now.”
Well, she made a good point—and the crew was lucky to have her because the film was a hit. However, professional successes didn’t always translate to her personal life…
20. She Kept Trying For Love
Despite the failed relationships that came before, Pearl Bailey never gave up on love. After all, it was the main subject of the songs she sang each night. Keeping her fingers crossed that the third time would be the charm, Bailey married John Randolph Pinkett in 1948. She was just 30 when she married him and she must have hoped this time was the real deal—but she quickly discovered that he had a disturbing dark side.
21. Her Husband Was A Disappointment
Unfortunately for Bailey, the third time was quite a disaster. Pinkett was basically a jerk who was unhappy with her singing career. But he took his unhappiness way too far, and physically abused her—one time, he even hit her with a telephone. Still, for four long years, Bailey put up with it…but even she had a breaking point.
22. He Went Too Far
Things came to a head one dark night in early 1952. That night, Pinkett “split [her] skull open” with a firearm. Bailey filed for divorce soon after, ending the four-year marriage. Thankfully, despite her turbulent personal life, her career hadn’t suffered. And luckily, Bailey’s patience and her belief that she’d find her true love would soon pay off.
She was about to meet the love of her life—the one who’d help her forget all the terrible men she’d encountered until then.
23. She Met Mr. Right
Bailey had kissed a lot of frogs to find her prince, but she finally found him in 1952. Louis Bellson was a drummer and bandleader who worked with Duke Ellington. He was crazy about Bailey and she was clearly ready to find love. Perhaps it was an unconscious decision, but this time she chose to go out with a man who was different from the previous ones she’d been with.
Naturally, this came with its own share of problems.
24. She Had To Face Some Obstacles
Not only was Bailey’s latest beau six years younger than her—but he was also white. This may not seem like a big deal now, but it was a huge controversy back in 1952. When the press printed some snide remarks about them, Bailey’s reply was unforgettable. She brushed it off, saying, “There is only one race, the human race.”
Sadly, Bellson’s own dad was against the marriage—and the reason he gave was absolutely horrifying.
25. She Wasn’t About To Let Anyone Bring Her Down
Bellson’s dad apparently sent Bailey a “strongly-worded letter,” discouraging her from going through with the wedding because he was in no mood to “have a colored granddaughter.” Luckily, Bailey was able to ignore his negativity and focus on her love. Bellson’s and Bailey’s moms totally had their kids’ backs, so that was a plus.
The bride and groom tied the knot in Caxton Hall, London, a historical place where many celebrities celebrated civil marriages. Around 50 of their close friends and family members gathered around to share their happiness.
26. She Found Her Happily-Ever-After
Bellson and Bailey were the real deal. They bought a home in California and named it Apple Valley Ranch. He left Duke Ellington’s band and became her music director after the wedding. He was never insecure because while she was busy he also worked with several other bands, gave clinics for drummers, and wrote new music. Needless to say, they were very happy together.
Her marriage brought her immense happiness and her career was on the rise. For once, Bailey had it all—but could it last?
27. She Sang For Some High-Ups
Just before her wedding, one of Bailey’s friends, an actor-turned-senator, asked her to sing at a Press Club lunch for the President, Dwight Eisenhower. Her audience there really appreciated her rendition of her signature song, “Won’t You Come Home, Bill Bailey.” Little did she know, she was about to get the opportunity of a lifetime.
28. She Had A New Circuit
Bailey had once played for the coal circuit in front of a rough-and-tumble kind of audience. She now became the toast of Washington, D.C.’s social scene, singing for politicians and policy-makers. She even got an invitation for President Eisenhower’s second inauguration. But still, the same old problems Bailey had faced before soon came back to haunt her.
29. She Had Some Critics
Not everyone felt impressed by Bailey’s success in the capital. A lot of reporters and journalists criticized her for her association with a government that was “painfully slow in empowering the nation’s Black population.” They claimed that her loyalties were suspect since she wasn’t part of a civil rights group and hadn’t joined any marches for integration.
Bailey had just the answer for her critics, though.
30. She Knew What She Wanted
Bailey held her head high and declared she had nothing to prove because she lived her life caring about everyone. She told them that she “walks with love and hopes it rubs off.” On top of that, Bailey continued to choose scripts, such as The Landlord and All the Fine Young Cannibals, with strong themes focusing on race issues.
31. She Was A Jet Setter
Bailey’s popularity in DC earned her opportunities to travel abroad as well. She became part of America’s effort to increase its cultural presence in the rest of the world. She got to go to several other countries and met all kinds of people. Never a shrinking violet, this exposure helped her talk comfortably to heads of state, educators, and diplomats as well as other celebrities.
Although she enjoyed hobnobbing with the rich and famous, these trips could be quite tiring as well.
32. She Was Worn Out
In 1965, Bailey returned home from one such trip abroad, feeling pretty low. She complained of low energy, “being in a fog,” and exhaustion. She was clearly going through some major health issues, but Bailey had no time to slow down. Sadly, the consequences were disastrous. Bailey was performing in a Manhattan club when she collapsed in the wings.
An ordinary person would rush to the hospital, but Bailey revived enough to perform for another hour, against her doctor’s advice. It was a dire mistake.
33. She Couldn’t Stop
Pearl Bailey ended up being hospitalized five times that year, twice because of previous heart seizures. Doctors put her on bed rest for three weeks and insisted she had to lighten her workload. But Bailey was no ordinary patient. Of course, it was while she was laid up in bed that she discovered another thing she was good at.
34. She Found A New Hobby
Bailey had been planning on writing an autobiography for a while. The three weeks in bed gave her ample time to start writing a rough draft for it. She also discovered that she enjoyed writing poetry. And while she didn’t complete it immediately, the three weeks of focusing on writing gave her enough material to publish The Raw Pearl in 1968.
However, when those three weeks of confinement were up, Bailey basically jumped out of bed and forgot all about writing for the time being.
35. She Gave A Huge Hit
Perhaps her time off had reenergized her—because Bailey’s comeback came with an amazing surprise. It resulted in her biggest hit yet. She played Dolly Gallagher Levi, a woman on the hunt for a husband, in Hello, Dolly! Her old friend Cab Calloway was her costar in this Broadway musical and the play opened to a full house night after night—for one simple reason.
36. Her Work Got Rave Reviews
Bailey was excellent as Dolly. So much so that a critic claimed “The audience would have elected her governor if she’d only name the state.” Needless to say, everyone loved Bailey as Dolly. She went on extensive tours to perform the play, and she even won a Tony for her performance. But would this run of luck continue unabated? Or were dark clouds on the horizon?
37. She Made A Big Move
Bailey’s big opportunities just kept coming. She got her own show on television once she stopped touring with Dolly. She hosted The Pearl Bailey Show on the ABC network and interviewed many famous celebrities, including Lucille Ball and Bing Crosby. Louis Armstrong also made his last appearance on TV on her show.
Bailey had cemented herself not only as a multi-medium star—but also as a show business legend. And then, her tireless energy took her even further.
38. They Recognized Her Worth
In 1970, President Richard Nixon named Pearl Bailey America’s “Ambassador of Love.” And it wasn’t just a vanity title—she took the honor extremely seriously. Bailey traveled to the Middle East in the 70s, shaking hands with the Shah of Iran before his downfall. She even sang for Egyptian president Anwar Sadat before his execution.
Of course, being constantly on the go began to take its toll…
39. Her Health Suffered
Baily was in Denver in 1974 when she collapsed again in her hotel room. The staff rushed her to the hospital where she discovered that the combined effects of exhaustion and high altitude had knocked her out. Bailey got back on her feet—but few knew that she was hiding a dire secret. As Bailey later revealed, her heart problems were so bad that during one of her episodes, she’d technically died for a few seconds.
While she bounced back, it became clear that she wouldn’t be able to keep up the breakneck pace forever.
40. She Had A Small Family
As the years wore on, Bailey and Bellson’s passionate flame never dimmed. They adopted a son, Tony, soon after their marriage, and had a daughter, whom they named, Dee Dee in 1960. The family lived happily on Pearl’s beloved Apple Valley Ranch, where Bailey stayed as often as she could between her work commitments, although the kids often traveled with mom too.
To say she was a positive role model would be an understatement…
41. She Went Back To School
Not content with all that she’d already achieved, Bailey decided she wanted to get a college degree as well. She graduated from Georgetown University with a degree in Theology in 1985. She even made it on the Dean’s List. At 67, Bailey proved that there’s nothing you can’t do if you put your mind to it.
42. She Won Honors
Bailey’s achievements did not go unrecognized. She won a Screen Actor’s Guild Lifetime Achievement Award, the USO named her USO’s Woman of the Year in 1969, and she even won a Bronze Medallion in 1968, which was the highest award a civilian could get in New York City. But it was the honors that President Nixon had given her that made her the proudest.
And luckily, he wasn’t the only one to recognize her worth.
43. She Worked For A Cause
President Gerald Ford formally appointed Bailey as Goodwill Ambassador to the UN in 1974. Ford may have thought the title was ceremonial, but Bailey disagreed. She participated in UN debates to come up with solutions for the Israel-Arab conflict and even took the floor to discuss the need to combat the AIDS epidemic at the UN and the World Health Organization.
She did not shy away from working with anyone, anywhere when it was for a cause she believed in—and there was a very particular reason for that.
44. She Was Big On Commitment
Bailey worked alongside Barbara Bush on a US literacy campaign. She would address young people and talk to them about the importance of committing to a cause and contributing to it. That’s what she believed in whole-heartedly: “I have a go-for-it attitude about education, about life, about everything…My religion is action. You can’t spend your life waiting around. You go for it.”
And that didn’t just apply to her professional life, either.
45. She Stood By The Ones She Cared About
Pearl Bailey had a big heart and she was a wonderful friend to many. One of her closest friends was another megastar with a scandalous past—none other than Joan Crawford. Bailey considered Crawford like her own sister and sang a hymn at her funeral. She was also very close to socialite Perle Mesta. When a friend was in need, Bailey would always take the time out of her demanding schedule to step up and be there for them.
And when the tables turned, Bailey’s family and friends stepped up for her too.
46. Her Lifestyle Caught Up To Her
After a number of health scares throughout the 70s, Bailey had bounced back—but you can’t cheat time forever. While her heart health hadn’t bothered her, she began experiencing knee problems in the 80s. In August of 1990, Bailey went in for routine knee surgery—never realizing the nightmare she was about to face.
47. She Faced Some Complications
Bailey’s surgery took place in Philadelphia, and she had a hotel room booked for her family to stay there while she recovered. The surgery had gone well and doctors had told Bailey she could leave. She packed up and went to the hotel room to recuperate—not knowing that something had gone horribly wrong.
48. It All Happened So Suddenly
The stress from the surgery had likely exacerbated Bailey’s ongoing heart problems. On August 17, 1990, she died suddenly in the hotel room where she was supposed to be recuperating from surgery. Her family and friends were both shocked and devastated. Pearl Bailey, a legend of the stage and screen, was gone at just 72 years old.
49. Her Family Mourned Her Until The End
A sudden death is always very hard for the family. Bailey left behind a grieving husband of 38 years, and her two kids, Tony, and Dee Dee. Bellson took her passing very hard and said he’d lost his “best friend.” The heartbreak didn’t end there. While Bellson lived for 19 more years, he sadly lived through his son Tony’s passing in 2004.
Dee Dee also died just five months after her father, and the Bellson-Bailey lineage ended with her.
50. She Was Larger Than Life
Bailey’s friends and family remembered her not only for her kind heart and never-say-die attitude, but also for her wit, her exuberance, and her wisdom. Countless sources mention how well she loved, and how universally loved she was herself. “She was sultry and statuesque, a muse in high heels. When she sang a song, she squeezed it with an earthy embrace that could warm a listener from the back of the neck to the soles of his feet.”
And it wasn’t just those close to her who recognized her worth and her contributions.
51. Her Name Lives On
After her passing, Bailey’s hometown of Newport News honored her by naming the town library after her. In 2018, on what would have been her 100th birthday, the library unveiled a mural of its namesake. But that’s not all. The popular TV show American Dad features a “Pearl Bailey High School,” so named as a tribute to the legendary icon, and the National Museum of African American History and Culture has a Pearl Bailey dress on display.