What would the holidays be like without the dulcet tones of Bing Crosby’s voice drifting through the air, whether it be in a department store, at a party, or in the background of a favorite old movie? While many of us associate 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. Here are 50 festive facts about Bing Crosby.
Bing Crosby Facts
1. A Rose By Any Other 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 past-time: playing Cops and Robbers. Apparently, the little crooner would say “bing bing bing” whenever he’d “shoot” at someone.
2. Just a Bit Disingenuous
However, this Cops and Robbers tale was apparently little more than a made-up origin story. Bing’s nickname actually came from a saucy neighbor who called Crosby “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.”
3. Tell Me What You Really Think of Me
Bing Crosby was so popular during his heyday that in 1948, an American poll named him “the most admired man alive.”
4. Good Things Come in Threes
Bing Crosby sang his iconic hit “White Christmas” in three different films, starting with Holiday Inn (1942), Blue Skies (1946), and, of course, White Christmas (1954).
5. Stuck in the Middle
Crosby was born into a large family. His parents Harry and Kate had Bing in 1903, and he was the fourth of seven children.
6. It’s Evolution, Baby
We may take it for granted today, but Crosby was one of the pioneers of a new style of American singing—which we now refer to as crooning. Before Crosby’s tenure at the top of the charts, many artists were accustomed to singing in a “belting” style that ensured their voices could be heard in every inch of a concert hall, even without microphones.
Crosby’s style of singing was quieter, smoother, and more well-suited to the sentimental songs of the era. It quickly caught on among his contemporaries.
7. One for the Road
While Bing Crosby may have been on top of the world in the 1930s, his marriage was paying the price for his fame. As a result of his popularity, Bing and his wife Dixie Lee were frequently invited to raucous parties, and Lee drank to keep up with Crosby and his friends. Her alcoholism got so bad at one point that Crosby contemplated separation.
8. Go Your Own Way
When he was a young man establishing himself on the music scene, Crosby spent years performing with the Rhythm Boys. But over time, it became clear that Bing Crosby was the shining star of the group. In 1931, he signed a solo recording contract with legendary producer and studio head Mack Sennett. Bing was about to make his mark as a solo artist.
9. Started From the Bottom
Bing Crosby began his solo career on the radio with a weekly 15-minute-long broadcast in 1931. He was an instant hit, and many of the best selling songs of that year were his. By 1932 he had been cast in his first feature-length film, titled The Big Broadcast—and that was just the start of his meteoric rise to fame.
10. Blue Christmas
However, behind the scenes, things weren’t so idyllic for Crosby. In 1930, he married an actress and singer by the name of Dixie Lee. At the time, she had actually been more famous than him. After six unhappy months of marriage, Lee announced that the couple had separated. In a disturbing twist, she intended to seek a divorce on the grounds of “mental cruelty.”
11. Kiss and Tell
Lee’s announcement of their separation was quite detailed—she even went so far as to say that “‘Bing’ is a fine boy as a friend, but married he and I just cannot be happy.” However, it didn’t take long for things to change between the young couple. Just a week after Lee’s announcement, they reconciled. A friend intervened and insisted that Lee call Crosby. After that, Bing flew down to see her in person—and the rest is history.
12. Happily Ever After
After their reconciliation, Crosby and Lee went on to have four sons: Gary, Dennis, Phillip, and Lindsay Crosby.
13. The Thin White Christmas Duke
While “White Christmas” may be Crosby’s most enduring Christmas song, he produced one heck of a tune when he teamed up with David Bowie in the fall of 1977 for his holiday special, titled Bing Crosby’s Merrie Olde Christmas. The odd pair were supposed to perform “The Little Drummer Boy.” When he got to set, Bowie revealed the terrible truth: He actually hated the song, and requested to sing something else.
A trio of songwriters came up with the counterpoint lyrics of “Peace on Earth” on the fly. The new song pleased Bowie, and after less than hour of rehearsal, the pair sang the new hybrid song.
15. Go Bulldogs!
Bing Crosby was a Gonzaga man through and through. After going to Gonzaga High School, Crosby then went on to Gonzaga University. While he never graduated, he received an honorary degree in 1937. Currently, Gonzaga U is home to the largest archive of materials related to Crosby and his career. The house he grew up in is even part of their property!
16. Forward Momentum
Crosby was influential in more ways than one—his support for and defense of his black contemporaries helped move things forward in the music and film industries. For example, he was a close friend and great admirer of Louis Armstrong. Crosby insisted that Armstrong appear in his film Pennies From Heaven, thereby ensuring he had a jump start in Hollywood.
Crosby was also adamant that Armstrong receive equal billing with his white co-stars.
17. Der Bingle
During the Second World War, Crosby supported the troops by making live appearances in Europe for them, and he also participated in Allied propaganda broadcasts meant to reach German soldiers. He learned German for these, and earned the nickname “Der Bingle” among the German troops. A post-war poll of American soldiers named Bing Crosby as the person who did the most for morale—even ahead of the American president at the time, Franklin Delano Roosevelt.
18. I’m Dreaming of the Guiness Book of World Records
Crosby’s most enduring legacy is the hit song “White Christmas.” It’s actually still the bestselling single of all time, and regularly experiences a resurgence in sales each year—around, you guessed it—Christmastime. The song, written by Irving Berlin, was first broadcast on Christmas day in 1941. After its original release, it was played so often that Crosby was forced to re-record it in 1947, as the master recording was disintegrating from overuse.
19. It Takes Two
Throughout their careers, Bing Crosby appeared alongside Bob Hope in over 25 films. Although they never officially acknowledged themselves as a duo, they were a comedy team to rival legends like Laurel & Hardy or Dean Martin and Jerry Lewis.
20. Triple Threat
Seven of the films that Crosby and Hope appeared in together were part of the Road to… series, which also showcased the actress Dorothy Lamour. Each film was a comedy, with many of them lampooning popular adventure film tropes of the period. An eighth was in the works, but it was scrapped due to tragic circumstances (more on that later).
21. College Dropout
In 1923, shortly after dropping out of Gonzaga, Bing Crosby proved that he didn’t need a college degree to be successful. The young crooner began what would eventually become an iconic career. He was a member of a number of singing groups in the early 1920s, before going on to work with jazz legends like Bix Beiderbecke and the Dorsey Brothers in New York City.
22. Alternative Alternatives
Bing Crosby had a progressive take on marijuana. In a 1977 interview, Crosby said that it should be legalized.
23. Through Sickness and in Health…
After years of marriage, Crosby and Lee had seen their relationship survive a fair share of trials and tribulations, but the worst was yet to come. Lee began experiencing health issues, and Crosby was by her side the whole time. In 1945, Lee collapsed and was rushed to hospital. It was said to be a respiratory infection, but this didn’t stop tabloids from speculating that she’d overdosed on sleeping pills.
24. …Til Death Do Us Part
In the early 50s, rumors swirled that Crosby and Lee were living apart, but by 1951 they were both back in their home in the Holmby Hills district of Los Angeles. Whatever the reasons for their separation, the reason for their reunion soon became apparent: Lee was very sick. On November 1, 1952, Dixie Lee passed away from ovarian cancer at the age of 42. Crosby was now a widower with four teenaged sons.
25. Bachelor: Hollywood Edition
In the years following the death of his wife, Bing Crosby dated a number of women, including actress Inger Stevens and Hollywood icon Grace Kelly, the future Princess of Monaco. Not bad for a single dad!
26. Hot Priests = Eternal Awards Bait
In 1944 Bing Crosby won a Best Actor Oscar for a film titled Going My Way, in which he played a young priest. He was also nominated the next year for the film’s sequel, The Bells of St. Mary’s.
27. Art Imitates Life
Although Crosby was frequent tabloid fodder in the 1950s, he got the chance to prove his talent in the dramatic film The Country Girl. Once again, his performance was a smash hit. He received a nomination for the Best Actor Oscar for the role, where he played an alcoholic entertainer—but according to many, the performance hit too close to home for Crosby.
28. Under the Influence
Throughout his life, it was rumored that Crosby was an alcoholic. First, there were stories from his early career that implied he’d been fired from an orchestra because of his drinking. One of Crosby’s biographers claimed that he’d once told his son Gary that alcohol had killed his mother, and to avoid it at all costs. Tragically, it’s been implied that Crosby’s first wife helped him to curb his drinking at her own expense, and that her troubles with alcohol stemmed from that.
29. Take Two
Five years after the death of his first wife, Crosby found love again with an actress named Kathryn Grant. They went on to have three children together: Harry Lillis III, Mary, and Nathaniel. Crosby and Grant were together until his death.
30. The Magnetic Magnate
Crosby was more than just a singer and actor. He was also quite the entrepreneur and owned several business and organizations over the years. Crosby was an investor in an L.A. recording studio, Minute Maid orange juice, and videotape recorders. He also owned a racehorse, multiple TV stations, a California stable, and a 25% stake in the Pittsburgh Pirates baseball team. Talk about someone being hard to Christmas shop for!
Somehow, Crosby also found time for hobbies. He was an avid golfer, with memberships to at least 75 different golf clubs—those membership fees surely added up to big bucks.
32. The Spirit of Radio
Allegedly, Crosby’s passion for golf inadvertently changed radio forever. The networks that produced Crosby’s radio shows insisted that they be broadcast live, but he pushed to be able to tape them in advance so that he could get out of the studio and onto the golf course whenever he pleased. He was so insistent on the change that he left NBC for seven months in the 40s.
Whether or not it was over golf, the truth is that he did fight hard to be able to pre-record his programs, and soon enough, this would become standard practice in radio.
33. No, Like, He Really Really Loves Golfing
Bing Crosby was originally offered the role of Columbo in, you guessed it, Columbo, the popular 70s detective TV series. He turned down the role because the filming of the pilot coincided with a golf tournament he was playing in.
34. His Second Most Enduring Legacy
Last golf tidbit…we promise. In 1937, Crosby threw a golf tournament that he named the “Crosby Clambake.” It became an annual event after the war, when it switched locations to golf courses in Pebble Beach. It’s now known as the AT&T Pebble Beach Pro-Am. That’s right, one of the biggest American golf tournaments was started by Bing Crosby.
35. Exit Stage Front
In March 1977, a concert was filmed to commemorate Crosby’s 50th year in show business. After he finished performing, a terrible accident transpired—Crosby slipped and fell off the stage into the orchestra pit as his friend and creative partner Bob Hope watched helplessly. It was a severe injury for a man of his age and it left him recovering in hospital for months.
36. Crooners Are a Dying Breed
When Bing recovered, he ended up playing what would be his final US concert, on August 16, 1977. Coincidentally, that was the day that Elvis died.
37. Small Choices…
During the Great Depression, record sales were down for understandable reasons—few people had the disposable income to buy them. At that time, artists were generally paid a flat fee for their work, but record label founder Jack Kapp had a crazy idea for how to get sales back up. He decided to charge 35 cents per single instead of a dollar. But what did Bing Crosby have to do with this?
38. …Make a Big Change
At that point, the flat fee that went toward the artist was so high that they never would be able to lower the price of a single to just 35 cents. To make Kapp’s idea work, the artists would have to switch from getting the fee to accepting a royalty for sold records. Crosby agreed to support this idea, and because he was a big name, many others followed suit.
It’s been said, for this reason, that Bing Crosby saved the recording industry during the Great Depression. At the very least, the shift from flat fee to royalties changed it forever.
39. Unlucky 13
Sadly, Crosby passed away on October 13, 1977, after experiencing a massive heart attack while returning from a game of golf at a course outside of Madrid, Spain. He was buried at Holy Cross Cemetary in California, but there’s also a commemoration plaque for Crosby at the golf course in Spain.
40. Forever on Brand
True to form, Bing Crosby’s last words were reportedly, “That was a great game of golf, fellas” followed by, “Let’s get a Coke.”
41. Fathers and Sons
After his death, Gary Crosby, one of his sons from his first marriage, dealt Crosby the ultimate betrayal. He wrote a book about his relationship with his father titled Going My Own Way. It was a real scorched-earth account of his life with Bing. Gary Crosby alleged that his father was cruel, distant, and abusive in every sense of the word.
42. Disturbing Claims
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.
43. Brother vs. Brother
Gary’s brother Phillip Crosby quickly jumped to their father’s defense, claiming that Gary was a “whining, [redacted] crybaby, walking around with a two-by-four on his shoulder and just daring people to nudge it off.” Yikes. While Phillip denied Gary’s claims, he did admit that Bing Crosby did believe in corporal punishment, but only when warranted.
44. Fightin’ Words
As harsh as Gary was toward his father Bing, Phillip was even more harsh 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.
45. Bad Luck Comes in…Fives? Sixes?
One would hope that despite their infighting that Crosby’s sons from his first marriage would find some measure of happiness in their lives, but tragically, that was not the case. Within two years of each other, both Lindsay and Dennis Crosby died by suicide. Gary Crosby died on lung cancer a few years later, followed by Phillip in 2004.
In a sad twist, Phillip died of a heart attack, just like the father he so tirelessly defended.
46. Chips Off the Ol’ Block
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 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.
47. All in the Family…
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 (and then posed for Playboy, in case the other parts weren’t attention-grabbing enough).
48. …And All Out of the Family
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.
49. Cold Blooded
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.
50. I’m Not Crying, You’re Crying
It must have seemed like Bing Crosby was inescapable during the 30s, 40s, and 50s—which isn’t to say his influence waned in the 60s and 70s, as he kept working right up until his death. He was undeniably one of the most beloved artists of his era. His most enduring work seems to revolve around the holiday season, and his friend and collaborator Bob Hope may have summed it up best in his autobiography.
Of his dear friend, Hope wrote “Dear old Bing. As we called him, the ‘Economy-sized Sinatra.’ And what a voice. God I miss that voice. I can’t even turn on the radio around Christmas time without crying anymore.” After reading that, neither can we.