While many of us associate Bing Crosby with the holiday season, he was more than just a carol singer. As an actor, singer, and comedian, he dominated both record sales and the box office—but behind the scenes, his life was defined by loss, heartbreak, and scandal.
1. He Had A Different Name
The man we now know as Bing Crosby was actually born with a different name: Harry Lillis Crosby Jr. In his heyday, Crosby attributed his unique nickname of "Bing" to his favorite childhood pastime: playing Cops and Robbers.
Apparently, the little crooner would say “bing bing bing” whenever he'd “shoot” at someone. However, this whimsical tale wasn’t exactly true.
2. He Twisted The Truth
In reality, Crosby’s nickname actually came from a saucy neighbor who called him “Bingo from Bingville” while the singer was growing up. Why? Well, even though Crosby lived in Tacoma and Spokane, Washington, the local paper was called "The Bingville Bugle”.
He’d used the other story to make his past seem more dramatic. But considering his scandalous fate, Crosby had more than enough drama to keep him afloat.
3. He Took A Risk
When he was only six years old, Bing Crosby discovered his first phonograph—and his life changed forever. His love of music followed him throughout his childhood and caused him to make a drastic decision.
In university, he took a risk, throwing away his aspirations to become a lawyer in favor of a wild dream: becoming a musical star.
4. He Had Many Copycats
In the mid-1920s, Crosby found his first slice of success, performing in a trio called The Rhythm Boys. This is where his passion for jazz took flight. In fact, his vocal prowess was so impressive, copycats began crawling out of the woodwork, including future star, Dean Martin. Everybody wanted to sing like Bing Crosby.
However, just as the crooner catapulted to fame—fate dealt him a cruel blow that almost destroyed everything.
5. He Almost Lost It All
Bing Crosby faced a huge obstacle when he came down with a case of laryngitis. One can even hear “a hoarseness…an unmistakable sign of strain” in the records he produced throughout the ‘20s and ‘30s. Little did he know, the worst was yet to come.
In 1931, his condition took a scary turn when doctors found a node on his vocal cords. They insisted that the singer rest his voice. But Crosby had an unforgettable response.
6. He Was Prideful To A Fault
There was no slowing down for Crosby. Foolishly, he decided to ignore his doctors’ advice. He continued to sing with reckless abandon—but that wasn’t the most dangerous part.
Having laryngitis was one thing, but Crosby also had a penchant for drinking. His love for the bottle only exacerbated his health problems, causing a shocking ripple effect.
7. He Destroyed His Voice
As Crosby continued to sing, he damaged his voice. By the mid-1930s, he had trouble reaching high notes and had no choice but to give up his fast-paced jazz numbers. But here’s the twist.
This change actually worked in his favor. Forced to sing slower ballads, he appealed to mass audiences, growing his fan base and becoming “the voice of the nation”. But sadly, stardom came at a high price.
8. He Had A Rough Start
Bing Crosby welcomed love into his life, marrying actress Dixie Lee in 1930—but their romance had a rough start. Only six months after tying the knot, Lee made a surprising announcement.
Apparently, the marriage wasn’t happy at all and she filed a divorce suit: “'Bing is a fine boy as a friend, but married he and I just cannot be happy”. Oh, but this wasn’t the end.
9. He Got A Second Chance
Turns out, Crosby’s bride had somewhat of a fickle nature. It only took her a week to realize that she’d made a mistake. While at a party, she confided to one of her girlfriends that her anger had subsided. The girl promptly dialed up Crosby on a long-distance phone and mediated a reconciliation.
However, despite working things out, this love story does not have a “happily ever after”.
10. His Wife Made A Huge Sacrifice For Him
After settling down, Dixie Lee decided to abandon her film career in order to focus on raising a family with Bing Crosby. In fact, when the couple had first met, Lee was far more famous that Crosby—a veritable rising star. But all that went out the window once she said, “I do”.
The couple seemed to be playing by the rules, but it led them down a heartbreaking path.
11. His Absence Scarred Her
Bing Crosby rose to fame while his wife stepped into the shadows. In truth, Dixie Lee had always felt “uncomfortable in front of the camera or an audience”. Meanwhile, Crosby thrived—his work taking him far and away from Lee.
Crosby’s son Gary later admitted, “I think she got lonely because Dad was working all the time”. To cope with her melancholy, Lee turned to an unfortunate habit for solace.
12. He Watched Her Succumb To Drink
For Bing Crosby, marriage was a balm to his former addiction to the bottle—and after meeting Lee, he gave up his excessive drinking. However, his wife ran in the opposite direction.
As Bing’s health improved, Lee’s faltered. She drank herself into a hole—and it had some serious repercussions.
13. His Children Suffered
Together, Crosby and Lee welcomed four sons into their lives: Gary, Phillip, Dennis, and Lindsay. But all four of them got a front-row seat to their mother’s spiraling addiction.
Years later, Crosby’s daughter Mary revealed that Lee was often so inebriated, she couldn’t leave the house, even passing out in front of the children: “She’d be, you know, on the floor, and I think that’s permanently scarring on just about every level for anybody”.
14. His Kids Paid The Price
Dixie Lee’s personal demons leached into Crosby’s life, no doubt having a psychological impact on the entire family. But even more horrifying, Crosby’s twins—Dennis and Phillip—suffered the most.
Apparently, there’s a good chance that the boys had fetal alcohol syndrome as a result of Lee drinking throughout her pregnancy. Experts at USC looked at photos of the boys and called them a “textbook case”. But this wasn’t the only personal tragedy in Crosby’s life.
15. He Lost Everything
Crosby had a gorgeous family home in Toluca Lake, Los Angeles that covered four acres—but it seemed that fate had it out for everything good in the singer’s life.
In 1943, disaster struck when a raging fire engulfed the house, destroying “most of the personal possessions the couple had collected”. Afterward, The New York Times revealed the cause of the blaze, only deepening the tragedy further.
16. Christmas Caused The Fire
This $250,000 fire may have razed Crosby’s life to the ground, but it began on the heels of the most joyous season—Christmas.
Lee and the children were in the process of dismantling their Christmas tree when a short circuit set it on fire. It was a brutal loss for Crosby, who waved goodbye to his many trophies, and even worse, his “prized collection of musical recordings”. What’s more? This depressing fiasco occurred only a year after Crosby recorded his most famous number.
17. He Recorded A Defining Tune
Though Crosby’s personal life was a mess, his career was golden—and he left a legacy of 1,200 songs. There is, of course, one classic song for which he will always be remembered, “White Christmas”.
For decades, it held the title of “Best-Selling Single” of all time in the Guinness Book of World Records. But some believe that this tune did Crosby more harm than good.
18. His Legacy Is Overshadowed
Despite his overwhelming body of work, Bing Crosby’s name has become inextricably linked with Christmas. Record producer Ken Barnes pinpointed why this poses a problem for the crooning legend: “History doesn’t see Bing [as a trailblazer]. History sees him as the guy who comes out every year and sings ‘White Christmas’”.
Crosby himself, however, had another opinion altogether.
19. He Never Resented “White Christmas”
In 1977, Bing Crosby appeared in an interview with Barbara Walters—and she asked him a very personal question. She wondered whether the singer was “sick” of his biggest hit. His response was downright heartwarming. He replied, “No, I could never be sick of it. I just fear the people would be sick of it”.
Clearly, Crosby spent his life associated with Christmas cheer—but behind the scenes, he was one of the messiest celebrities around.
20. He Was A Poor Father
Bing Crosby may have been an excellent singer, but he was also a lackluster father. The man’s busy schedule meant that he was always absent. He later confessed that because he filmed up to four pictures a year, he rarely spent time with his four boys, whom he sent to boarding schools.
But there was an even darker side to his parenting.
21. He Had A Deep-Seated Fear
Crosby knew that celebrity children often struggled to make their way in the world. He became increasingly obsessed with the notion that his own sons would face corruption. Crosby feared that they’d grow into the spoiled, rich kids he himself detested.
His son Gary shared, “He always said he didn’t want any Hollywood kids in the house”. But unfortunately, Crosby’s fear only created a harmful distance. And as we’ll see, this was only the tip of the iceberg.
22. He Watched Her Waste Away
Crosby’s marriage to Lee was never smooth-sailing. In the back of his mind, he wondered whether he’d be better off getting a divorce. However, despite his nagging doubts, he stood by her. Unfortunately, his loyalty couldn’t spare him from heartache.
In January 1945, Dixie Lee collapsed from a so-called “respiratory infection”. But the truth may have been far more disturbing.
23. He Almost Lost Her
Crosby stayed by his wife’s side after an ambulance rushed her to St Vincent’s Hospital. He spent the entire night with her, fearing that she wouldn’t make it. Then a chilling article came out.
Picturegoer magazine wrote that Dixie Lee may not have had a physical illness, but rather that she’d accidentally taken too many sleeping pills. Unfortunately for Crosby, this wouldn’t be the last medical scare.
24. He Watched Her Fade Away
A cloud of loneliness hung over the Crosby family. It eventually transformed into a storm of unbridled grief. You see, Dixie Lee was not well. For decades, her loneliness and depression—not to mention her drinking—drove her to the very edge. She’d already been through the wringer, but her life was about to reach a whole new level of awful.
At the age of 40, she received a heartbreaking diagnosis.
25. He Never Told Her
Crosby’s wife Dixie Lee had ovarian cancer, but that wasn’t the saddest part. Her doctors knew her illness was terminal, but decided not to tell her; they didn’t want her to know.
To further the ruse, Crosby himself flew out to Paris to film a movie, thereby not raising any suspicions. This, however, was a terrible mistake.
26. His Grief Shocked His Sons
Crosby’s wife passed, but he wasn’t there when she closed her eyes forever. Lee passed at the young age of 40, and her husband’s absence made her demise even more heartbreaking.
The famous crooner had lost the love of his life. Drowning in grief, he faced the day of her funeral—and his broken demeanor shook his children to their cores.
27. He Had Another Woman
According to Crosby’s son Gary, the day of the funeral was unforgettable, with photographers swarming the private function: “It was a freaking circus. Through it all…it was like he was alone”.
Crosby’s heartbreak caused him to retreat into a shell of privacy, and he refused to talk about his grief to the press. But here’s the scandalous part. Dixie Lee wasn’t the only woman in his life.
28. He Had A Scandalous Affair
In the late 1940s, while poor Lee drank her life away, Crosby slipped beneath the sheets with a mistress: actress Joan Caulfield. But this sordid affair didn’t come out until much later.
Fellow actress Patricia Neal exposed Crosby’s infidelity in her autobiography As I Am after she spent time on a cruise ship with Caulfield. After all, she was no stranger to being a mistress herself.
29. He Was All She Wanted
Bing Crosby’s secret came out after his death, no doubt slandering his image as a loyal husband.
Patricia Neal wrote, “[Joan Caulfield], too, was in love with an older married man who was quite as famous as Gary [Cooper]. She confided to me that she desperately wanted to marry Bing Crosby. We were in the same boat in more ways than one, but I could not tell her so”. But the hot gossip doesn’t end there.
30. His Stalkers Caught Him In The Act
Believe it or not, Crosby had two stalkers—sisters Violet and Mary Barsa—and they knew what he was up to long before the rest of the world did. After tailing the high-profile singer, they’d write down their observations in their diaries. And boy, were they eye-opening.
Turns out, Crosby was indeed visiting the theater and opera house with Caulfield, frequently meeting her and her mother. But that wasn’t all.
31. He Loved Her
Caulfield’s own sister, Betty, also put a stamp of confirmation on Crosby’s extramarital relationship. What’s more? Crosby was completely in love with Caulfield and even considered leaving his wife for her.
Being a staunch Catholic, Crosby wrestled with the idea of divorce. He wanted to do the right thing, but at this time, Dixie Lee’s personal problems were taking a heavy toll on their marriage.
32. He Needed Help
Desperate for some advice, Crosby turned to two leaders for guidance: a Cardinal and his own mother. Of course, Cardinal Francis Spellman did not give him the answer he probably wanted to hear.
According to Betty Caulfield, Spellman said, “Bing, you are Father O’Malley and under no circumstances can Father O’Malley get a divorce”. Crosby’s mother only echoed the Cardinal’s sentiment, therefore sealing the crooner’s romantic fate.
33. He Became A Bachelor
Despite his feelings for Caulfield, Crosby felt obligated to stay with his wife. But after she passed, he took full advantage of his new status as a bachelor. He dated a number of famous women, including Pat Sheehan, Grace Kelly, and Inger Stevens. But in the end, it was actress Kathryn Grant who won his heart.
For Crosby, it was a second chance—but this new union created some bittersweet fallout.
34. He Treated His New Family Better
After Crosby married Kathryn Grant, his family expanded. He welcomed three more children. But sadly, it felt more like a second family. With his career slowing down, he finally had time to dedicate to his second batch of kids. And this created a startling juxtaposition to his first four kids.
His son Nathaniel later expressed, “As far as raising kids, he didn’t have a clue. I can’t say what happened with my father’s first family. I believe he had more time to spend with us”. However, this wasn’t the only major change in Crosby’s life.
35. He Took A Back Seat
As Bing Crosby grew older, the world changed dramatically. Younger stars like Elvis Presley and The Beatles took center stage and contrasted Crosby’s dapper image. Still, in 1977, the music industry gave the crooner a special honor.
To celebrate his “50 years in show business,” there was a televised special produced just for him. But horrifyingly, it almost had fatal consequences.
36. He Took A Tumble
The night of Bing Crosby’s TV special was supposed to be a celebration, but it quickly turned into a nightmare.
At the end of his performance, the elderly Crosby fell off the stage. Luckily, he managed to grab onto a piece of scenery on his way down, cushioning his hard fall. But he didn’t walk away unscathed.
37. He Couldn't Walk
As a result of his accident, Crosby ruptured a disc. He couldn’t stand, let alone walk. His daughter Mary Crosby revealed that he was lucky to be alive: “It should have killed him. It didn’t, but it should’ve”.
This was a terrifying close call, but sadly, the star’s days were already numbered. In fact, his end was so sudden—nobody saw it coming.
38. He Played One Last Round
On October 13, 1977, Crosby made a fateful journey to Spain, hoping to unwind with some golf and hunting. The very next day, he was out on the golf course in the best of spirits.
When he reached the ninth hole, a group of construction workers recognized the star and requested that he sing them a song. Crosby happily indulged them and performed “Strangers in the Night”. Little did he know, he would never live to see the next day.
39. He Collapsed
To his delight, Crosby won his very last game of golf. On his way back to the clubhouse, he turned to his friends and said, “That was a great game of golf, fellas. Let’s go have a Coca-Cola”. These were the last words he ever uttered.
Only 20 yards from the clubhouse, Bing Crosby suffered a massive heart attack, fell to the ground, and never woke up. The 74-year-old legend had passed in the blink of an eye…but his story was far from over.
40. His Son Exposed Him
Shockingly, Bing Crosby’s worst secrets and tragedies came after his passing. To begin with, his image was completely thrown under the bus.
You see, everyone thought that Crosby was squeaky clean—an “ultra-square pop crooner”. It seemed like he’d go down in history for being one of the good ones, that is until his eldest son, Gary Crosby, published his scandalous memoir in 1983, Going My Own Way.
41. He Brutally Mistreated His Children
Gary Crosby went ahead and rewrote history, claiming that his father had terribly mistreated him and his siblings, both emotionally and physically. His earth-shattering tell-all completely shifted the public’s perception of Crosby.
In one passage from the book, Gary Crosby alleges that Bing was critical of his weight, and would hit him with a metal-studded belt if he failed to live up to his father’s expectations after a weekly weigh-in. Oh, but the betrayals didn’t end there.
42. His Favorite Son Hated Him
Gary Crosby’s chilling memoir wasn’t the only shock. You see, Crosby’s other son, Lindsay, completely sided with Gary’s claim, confirming his viciousness once and for all. This was all the more surprising considering Lindsay was supposed to be Crosby’s favorite child.
The entire fiasco shed light on Lindsay’s heartbreaking personal struggles.
43. He Couldn't Save Him
Lindsay was a troubled man. Even in adulthood, he struggled with drinking and depression. Bing Crosby was so worried about his condition that he even considered committing him to a psychiatric ward.
But in the end, there was no hope for Lindsay. He ignored his father’s pleas to get healthy—and things only got worse from there. Even after Crosby passed, Lindsay continued to follow a dark path—and it led him straight to a terrible end.
44. He Left Behind A Tragic Legacy
In December 1989, Lindsay made a disturbing discovery: His family inheritance was all gone. In a moment of hopelessness, he did the unthinkable—and took his own life.
According to a representative for Gary Crosby, Marilyn Reiss, the youngest Crosby had spent years wrestling with addiction and had the added “strain of living under the shadow of his famous father”. Unfortunately, more heartbreak was just around the corner.
45. His Sons Never Stood A Chance
It seemed like Bing Crosby’s first family was doomed. All four of his sons from his marriage to Dixie Lee became heavy drinkers. Sadly, Lindsay wasn’t the only one to take his own life.
56-year-old Dennis shot himself. At his memorial service, his brother explained how their mother’s passing had severely affected Dennis: “I saw the light go out of his eyes. As far as I’m concerned, he’s been trying to get back to her ever since”. Of course, the drama within the Crosby family went even deeper.
46. He Had Someone In His Corner
One brother was not on Gary Crosby’s side and did not agree with any of the sensational claims that Bing Crosby had been a horrible father. The allegations enraged Phillip Crosby—and he threw it all back in his brother’s face.
He said that Gary was only after celebrity and money. But that wasn’t all.
47. He Was Their Golden Ticket
As harsh as Gary was toward his father Bing, Phillip was even harsher toward Gary. He called him a liar, ugly, talentless, greedy, and money-grubbing. The cherry on top? He also said, “To my dying day, I'll hate Gary for dragging Dad's name through the mud". Ouch.
However, there was one silver lining for this messed-up family.
48. His Second Family Thrived
Thankfully, things weren’t quite so dire for Crosby’s children from his second marriage. His son Harry appeared in the original Friday the 13th before becoming an investment banker, while his daughter Mary was on the hit show Dallas.
Meanwhile, his son Nathaniel followed in his father’s footsteps in a different way—he became a golfer and became the US Amateur champion in 1981.
49. He Fell For A Model
One of Crosby’s relationships took a dark turn. He briefly dated (and even proposed to) a model named Pat Sheehan after the death of his wife. Not so scandalous, right? Well, Sheehan went on to marry Dennis Crosby in 1958. That’s right, first she dated the father, then she married the son.
50. He Faced A Huge Scandal
The honeymoon period for Dennis Crosby and Pat Sheehan was disturbingly short. Soon after their wedding, Crosby became the defendant in a paternity suit brought on by a woman named Marilyn Miller Scott, who claimed that her daughter was Dennis’s.
Dennis Crosby ended up on the losing side, and the long and drawn-out suit and its aftermath were extremely embarrassing for both Dennis and Bing Crosby. Perhaps as a result of the rancor between Scott and the Crosbys, Bing allegedly never met the granddaughter who was the subject of the paternity suit.