Why Bing Crosby Still Matters in American Memory Before Sinatra and Presley, Bing Crosby defined American popular culture.

Unless your parents bought his Christmas album, you have to be old to even know who Bing Crosby was. Yet he was arguably the first to bring us “pop music,” the first multimedia artist, and one of the best selling recording artists of all time. Estimates vary, but PBS reported that Crosby “sold close to one billion records, tapes, compact discs, and digital downloads around the world.” His songs hit the charts 396 times—more than Frank Sinatra (209) and Elvis Presley (149) combined.

Try counting on your fingertips Bing Crosby’s commercial recordings—more than 2,000—or his 4,000 or so radio programs. Then add early vaudeville, entertaining the troops in World War II, early silent pictures, award-winning motion pictures, and television specials. From 1944 until 1948, he was Hollywood’s top box-office draw. His “White Christmas” set a Guinness World Record as the best-selling single of all time. His nonchalance inspired Frank Sinatra, Dean Martin, and the list goes on. “He is the one,” said Tony Bennett, “who has shown us all how to do it.”

What is left of all that, in our minds? Jokes about orange juice (Crosby invested in Minute Maid), and a maudlin Christmas carol. Until a few months ago, when a musician friend raved about Bing Crosby’s genius, I had paid the man zero attention. Not because he predated me—so did Ella, Sinatra, Sarah Vaughan, Louis Armstrong. But compared to them, Bing just seemed bland, irrelevant, over.

Why?

• • •

The young crooner in a 1936 “Radio Mirror” poster (Wiki Commons)

You can picture him as a kid: towheaded and a little chubby, with stick-out ears and his shirttail out too. His pranks were the sort that forced adults to hide a grin: raiding a bakery truck for cinnamon buns, running logs on the millpond, hitching rides on railroad trains. He was good-natured, too, when the pranks were played on him. Once, before physics class at Gonzaga University, his pals lured him into a storage space and locked the door. Did Bing bang on the door? No. He waited until the lecture began, then started singing “The Missouri Waltz.”

Even his nickname made him popular: “Bing” was as casual as he was, fun to say, boyish and direct. Though smart, he was not studious; he cared more about sports. Though a devout altar boy, he was eager for fun. And though he came off as carefree, he grabbed any job he could get: lifeguard, caddy, postal worker, boxing usher, woodchopper, sweeper at a flophouse. His dad, a bookkeeper, had never been able to hang on to his own money. Easygoing and pleasure-seeking, he adored music and would splurge on a record player, radio, or piano, rather than clothes or food for his seven kids. There was never enough cash for comfort.

It is said that we live the unlived lives of our parents. As a teenager, Bing joined a local band as a drummer, practicing in the basement of Benny Stubeck’s Confectionary. When the band broke up, Bing and Al Rinker became a singing duo. As they left Spokane to try their luck on the West Coast vaudeville circuit, Bing wrote to his mother (who wanted him to become a priest): “My chief desire is making out in a big way quick and doing something for you that will really matter.”

He and Rinker bought a Model T and headed south to Los Angeles. Soon they were invited to join Paul Whiteman’s jazz orchestra as The Rhythm Boys. But whenever Bing sang a solo, audiences fell under his spell. The nonchalance that had sailed him through childhood kept his ballads from turning mawkish. And that voice. It carried all the emotion he never expressed any other way. And it controlled that emotion, modulated it, kept it from ever riling us. Now it was emotion placed in service of the music, not music as a vehicle for emotion.

In the panic and uncertainty of the Depression, people appreciated that restraint. In 1929, Bing Crosby made his first solo record. By 1935, he was hosting Kraft Music Hall on NBC radio, drawing an estimated 50 million listeners with his easy, intelligent banter and musical guests—some classical, some pop—from all over the world. Changing what we knew, and loved, about music.

• • •

If you dig up Birth of the Blues, you can see the rather pathetic musical world that preceded Bing Crosby. White men warbled high as Irish tenors or smeared on blackface, because the real music was not their own. As the film opens, a White boy is playing a horn, imitating the Black Dixieland jazz he hears. The kid becomes our hero; the Black musicians remain caricatures, “happy Negroes,” elated by the White musicians who have taken their music. But the kid does not know he is stealing; he is just admiring and joining in. “It kinda turns you loose inside,” he tells his disapproving father.

Bing felt the same way. In the film, he sings as he shoots pool, doing both with the same loose-limbed ease. He slides into song as though he is making an offhand remark, yet the result is melodic, his timing flawless.

Years later, when he recorded in England, the British jazz musicians backing him up were so blown away by that timing, they decided to mess with him a little. “No matter what they did, they couldn’t knock him off his stride,” recalls his premier biographer, respected jazz critic Gary Giddins. After the session, Crosby grinned and said, “I’ll tell you why you couldn’t. When I’m listening to the beat, all I’m listening for is the one,” the downbeat of each measure. “I don’t care what you put on top of it.”

He had other gifts, too. Perfect pitch. A pace so relaxed, it gave the rhythm time to enter your body. A light baritone easy on the ears, with a tenor top that let him slide fast between the octaves. Vocal cord nodes that made his voice husky in the early years, sexy without trying. And enough Irish in his blood to sing the mordents—quick embellishments that went up a note and down again—unselfconsciously.

Bing’s Jesuit professors had drilled him in elocution and taught him that each word mattered, so when he sang a lyric, its meaning always landed. If the phrasing was awkward, he could smooth it on the spot. He had a startlingly fancy, yet unstuffy vocabulary. Tickled by alliteration and wordplay (he called his TV audience “captives of the coaxial cable”), he could always liven up a scripted response. (When someone said “I didn’t want to be tarred and feathered,” he was supposed to reply “Can’t blame you” but instead retorted, “There ain’t that many feathers.”)

His first genius was jazz. But Jack Kapp, a producer with Decca Records, soon realized he had somebody who could break out of genre. He called a halt to the scat singing Crosby had learned, with delight, from his pal Louis Armstrong. There would be no more “bu-bu-bu-boos.” Crushed, Bing went out and got drunk. Then he came back and let Kapp turn him into an American troubadour, singing not only the standards of the Great American Songbook but also Irish ballads, country songs, light opera, show tunes, funny songs, Christmas carols, liederspiel, and Hawaiian lullabies. “He became something that had never existed before,” Giddins says, “and I don’t think it has existed since.” Today, we are far too niche to let an entertainer range that far, pulling us all together.

Though Bing credited his career to Kapp’s intervention, jazz was wired into his body. He could make a ballad or a lullaby swing like a kid on the playground. And when he invited jazz musicians onto his radio show, that became a playground. In the sixties, when his American audience lost interest, he put together a jazz ensemble and paid for the recording himself. Giddins thinks Bing With a Beat “is his best. He’s just having the time of his life.”

I bet I would have loved Bing Crosby if he had stayed with the music he loved best. But then, Giddins reminds me, “he wouldn’t have been Bing Crosby.” He sighs. “Jazz is so misunderstood in the United States. You can go to your grave without even hearing it. We don’t retain our cultural history.”

Crosby did try. He added jazz’s colors and rhythms to other American music, swiping away the fussiness of the tenors who preceded him. But he spilled his talent across so many genres, pleasing so many crowds, that he wound up as boring as the postwar suburbs.

• • •

In 1930, ordered to appear in court after a traffic accident, a young Bing showed up jaunty in his golf knickers.

“The arresting officer said you had been drinking,” the judge said.

“Quite,” Bing replied.

And was he familiar with the Prohibition laws?

“Only remotely.”

The gavel clunked down: he would serve thirty days. Someone else would get to sing in the movie King of Jazz. “My crooning style wouldn’t have been very good for such a number,” he reflected later. “I might have flopped.”

That ability to shrug off mishaps was as crucial to his success as the rich timbre of his voice. Bing’s nonchalance assured us that he was never upset, never cowered in the face of authority, never sweated bullets over some possible gain or loss. It was the ultimate confidence, rinsed of agenda. And it was the perfect antidote for a nation whose fortunes had just crashed, and whose future was a terrifying unknown.

“He is the most relaxed, comfortable, comforting man,” said Mary Martin. “No matter what happens he can ad-lib, cover up, carry on. He can even sing with gum in his mouth; he just parks it over on one side.” Asked if he ever lost his temper, Bing replied, “I don’t have any temper to lose. In fact, I can’t remember ever getting really mad.”

On another occasion, he told a reporter, “I don’t worry seriously about anything.” What about marital disagreements? If something seems unsolvable, he said, “then the only thing is to go fishing or go golfing and then the seriousness will abate and you are finished with it.”

A therapist today would be appalled.

• • •

Crosby was hardly a pin-up. Sloping forehead, pale skin, sharp features. Imagine how it would have felt to have all eyes upon you—in the most appearance-driven part of an image-crazed nation—and be short, balding, and prone to belly fat, with ears that stuck out like handles. Hollywood kept trying to pin them back, but when the set’s hot lights melted the glue, Bing said, “Enough.” Sick of being told to wear “scalp doilies,” he switched to jaunty hats. Told his socks did not match, he shrugged and said, “Well, what the hell. I’ve got socks on, haven’t I?”

He refused star billing. Any movie he made had to feature at least two names, never his alone. He split the limelight, doing duets that became a pop music standby. He pooh-poohed praise. Of “White Christmas,” he said “a jackdaw with a cleft palate could have sung it successfully.” Adulation horrified him: “While I don’t mind signing a few autograph books, I get panicky if they start crowding in on me,” he told Motion Picture Magazine in 1942. “Worst of all, I can’t stand it if a fan starts getting gushy. If I see that coming, I duck!” Crosby resisted studio audiences because he did not want to feel obliged to amuse them. Nor could he tolerate canned laughter or advance applause, people clapping the minute he appeared. “I haven’t done anything yet,” he protested.

Fans loved him for minimizing his talent, making himself one of us. His Oscar for acting only proved, he said at the mic, “that everybody in this country has a chance to succeed. I was just lucky….” Faux humility? I am not sure. He really did seem to think his success a fluke and his talent “so thin it’s almost transparent.” In his autobiography—which he titled Call Me Lucky—he quoted his mother’s crisp correction: “Your luck has been my prayers and the prayers I’ve asked the Poor Clare nuns to offer up for you.”

Freud would have started and ended this piece with Kate Crosby, and he might not have been wrong. Because she so wanted her beloved Harry (she hated the diminishment of “Bing”) to become a priest, anything else was already a failure. Is that why he avoided any praise that might raise expectations he would then have to live up to? Of the seven Crosby kids, he was the only one who steadily defended their stern, strict, opinionated mother. When the others complained about how seldom she showed affection, he snapped, “She was probably cleaning your dirty diapers.” Before remarrying, he wrote to his mother seeking her blessing. Soon she had moved in with them.

But she already lived inside his head.

• • •

Boyish, athletic, God-fearing, self-made, and unpretentious, Crosby was the sort of man this country idolized. His career’s early 1940s peak coincided, Giddins notes, with “the vibrant highs of American civilization at its irreverent best.” He saw his rise as a Horatio Alger story and his luck as an American commodity. He would always be middle class, he insisted, even if he became a jillionaire, because being middle-class meant opposing aristocracy.

Fiercely patriotic, Crosby felt renewed by the soldiers he entertained during World War Two. Der Bingle, the soldiers called him. They wept without shame when he sang “White Christmas” to them. He wrote letters to the parents of soldiers with whom he took photos not yet called selfies. He risked his life, singing as bombs dropped, crawling through fog during a blackout, even getting lost behind enemy lines. He sold more war bonds than any other celebrity, and when U.S. troops were asked who had done the most for their morale, Bing Crosby topped the list.

A trailer screenshot of Bing Crosby as Father O’Malley in The Bells of St. Mary’s (1945), also starring Ingrid Bergman (via Wikimedia Commons)

He did his part in a subtler way, too, making a big deal of his Irishness to counter Father Coughlin’s viciously antisemitic radio broadcasts. When the war ended, and faith—in God and human nature—was shaken, he made The Bells of St. Mary’s, about a buoyantly optimistic priest who saves a school. [Editor’s Note: Leo McCarey’s The Bells of St. Mary’s was the 1945 sequel to the 1944 film, Going My Way, also directed by McCarey, for which Crosby won the Academy Award for Best Actor portraying Father Chuck O’Malley. He was nominated for the sequel as well but lost to Ray Milland who played an alcoholic writer in The Lost Weekend. Crosby became the first actor in history to be nominated more than once for playing the same character in different films. He was also nominated for Best Actor for the 1954 George Seaton film, The Country Girl, for which co-star Grace Kelly won for Best Actress. Unlike the Leo McCarey films, which were heartwarming semi-musicals, The Country Girl is a drama in which Crosby plays an alcoholic, washed-up actor and failed husband. Going My Way won seven Oscars including Best Picture and was so successful at the box office that Crosby was named the nation’s number one box office attraction that year. The Bells of St. Mary’s was also the highest-grossing movie of the year of its release. In comparison, Frank Sinatra won the Academy Award for Best Supporting Actor for Fred Zinneman’s 1953 film, From Here to Eternity. He was nominated for Best Actor for Otto Preminger’s 1955 film, The Man With the Golden Arm but lost to Ernest Borgnine who won for Marty. Crosby was nominated once for a Golden Globe Award for Here Comes the Groom, 1952. Sinatra was nominated three times for the Golden Globes for Best Actor and won twice: Pal Joey in 1958 and From Here to Eternity in 1954. Elvis Presley was never nominated for an Academy Award or a Golden Globe. By this measure, both Crosby and Sinatra were far more accomplished actors than Presley. Crosby, because of the number of times he was nominated for the Best Actor Oscar, has an edge over Sinatra.]

But I really start to love him when I read about the real friendship between him and Louis Armstrong. Their musical gifts meshed, and they shared the same sort of gentle irreverence, the kind only possible because it springs from faith. Armstrong described his friend’s voice as “gold being poured out of a cup.” Crosby called Armstrong “the beginning and the end of music in America.” So when a TV sponsor said Armstrong would be too controversial a guest, Bing said fine, take him off, “but I won’t be there either.” He went to the mat for Armstrong in Pennies From Heaven, too—with the result that Armstrong became the first Black performer billed as a lead in a White film.

• • •

There were small deceptions along the way. Bing joked—but he also slid lifts into his shoes and laced up a corset as needed. When his firstborn, Gary Crosby, went through a pudgy stage, Bing mocked him cruelly—self-hatred disguised as discipline?

The “everyman,” nobody-special persona had a few cracks, too. Biographer Barry Ulanov writes that Bing would listen attentively to someone expounding on high opera, inserting only a polite “Really?” or “You don’t say”—then walk away whistling one of the lesser-known melodies from that opera.

His refusal of star billing, I found moving. What humility, what team spirit. Then I read a colder version of his rationale: if a movie flopped and he was the main star, it could ruin him.

As for his famous laziness, it was a fiction. Sure, he fished and golfed, but at his peak, he was also making several movies and multiple albums in a single year. Jimmy Cagney saw him drenched with sweat after a performance and realized that “the apparent effortlessness was a part of his very hard work.” Paramount had taken one look at the fishing hats, Hawaiian shirts, and torn sweaters (Bing being both color-blind and indifferent to fashion) and decided to sell the persona he had already begun to cultivate. They even “reproached him for working alongside his laborers when he renovated the property,” Giddins writes, “since it meant the makeup department had to disguise his blistered hands.”

The campaign—aided by a little pancake makeup—worked. “It is impossible not to love the character stitched together in Paramount’s press office—generous, naïve, humorous, happy, modest, unpretentious, pleasingly eccentric, devoted to family, bemused by good fortune,” Giddins concludes. But while some of that was to some degree true, the man was far more complex.

Bing Crosby, Louis Armstrong (center), and friends (photo by Manfred Selchow via Wikimedia Commons)

When Crosby’s first radio show had to be delayed, he said he was hoarse from too much singing. Others suspected an attack of nerves, which he found insulting, insisting that he had never had a moment of stage fright. After days of sweaty nausea when he sailed to France during the war, he insisted just as staunchly that he had not been seasick for a minute. When he fell more than twenty feet into the orchestra pit, rupturing a disc at the base of his spine, he sang “Off we go into the wild blue yonder” as the paramedics wheeled his gurney to the ambulance. He recovered fast and proved it, doing a little two-step on camera with Barbara Walters.

Still, he must have been shaken. At the close of the first concert he gave after the fall, he stepped away from the mic and said, “I love you” to the audience, hugging himself close as proxy. It was the most, perhaps the only, demonstrative gesture of his career.

• • •

If a man who attains wealth, international fame, and a supremely comfortable life can be a tragic hero, that is Bing Crosby.

His first wife, Dixie Lee Carrol, was shy, uncertain, lonely, reclusive, and volatile. She hated Bing’s absences but was reluctant to accompany him. After she stopped Bing from drinking too much, she started. When she was pregnant, the family doctor (who also drank to excess) told her she was rundown and prescribed brandy and milk. Relatives and physicians have speculated that all four boys had fetal alcohol syndrome. They all struggled with booze and depression, and two shot themselves.

Priests urged Bing to remain married, and so he did, until Dixie died of cancer. His best friend and favorite accompanist, guitarist Eddie Lang, had died years earlier, after Bing urged him to have a tonsillectomy. Eddie’s voice had gone craggy, and Bing wanted him to have a singing part in their next film. Though it was a simple surgery, Eddie suffered a fatal blood clot. Bing said so little afterward, people thought him cold, not realizing that love had twisted into guilt. He rationalized it away, saying Eddie might have died of the infection if he had not had the surgery. But he never let anyone get that close to him again.

Instead, he locked away his problems and focused on work, golf, and fishing. He glided through the 1920s, 1930s, 1940s; through vaudeville, radio, records, movies. New technology did not scare him. When he started performing, singers were using megaphones, like cheerleaders, to amplify their voices. The invention of the microphone allowed a more relaxed approach that was perfect for his light baritone and laidback delivery. A mic quieted his voice into resonance, injecting an intimacy I suspect he would have been uncomfortable summoning any other way.

When the Kraft Music Hall producers refused to let him pre-record on a wax disc, he volleyed back, taking his show to ABC. “Mr. Crosby has delivered a major, if not fatal, blow to the outworn and unrealistic prejudice against the recorded program,” The New York Times announced. Bing formed a company to develop new products, and one of his engineers borrowed and refined a German technique for recording cleanly on tape, with none of the surface noise of vinyl. Other networks soon followed his lead, and live programming died away.

“He was the first guy to take the carbon mic out of the studio,” says Giddins. “He financed the introduction of tape, and he revolutionized radio. The first canned applause in history came because one of his shows was forty seconds short, which never happened, so they spliced in some applause.” Which, of course, he loathed.

But he kept up, decade after decade. And then the world changed. Rock ’n’ roll seemed only interested in making teenage girls swoon, which appalled him. “Elvis will never contribute a damn thing to music,” he snapped.

By then, his own drive was flagging. In 1954, he admitted, “I don’t sing anywhere as good as I used to…. I am not keen about it any more. Songs all sound alike to me, and some of them so shoddy and trivial…. It seems to me that possibly this apathy, this lack of desire, when I have to go to a recording session, transmits itself into nervous exhaustion and fatigue.”

Halfway through, and he was bored? Maybe this was just a good old-fashioned midlife crisis. Or he worked too hard, all the while pretending he was not working at all. His marriage to Dixie could have taken the stuffing out of him. Did his reluctance to feel—anger, sorrow, fear, anxiety, passion, remorse—keep his artistry at the surface, a bit of performance and trickery that now felt dried-up and hollow even to him? Or was he just prescient, sensing a societal shift that would soon leave him behind?

Bing was born in 1903, so his life paralleled the decades of the twentieth century. In the twenties, he was a rogue and a playbaby, flask in hand. In the thirties, he became a warm and easy balladeer, soothing the nation through the Depression. During the war years, he was a staunch patriot. By the fifties, he was smooth and grown-up—but disenchanted.

And in the sixties, everything that had worked for Bing Crosby stopped working.

The nonchalance that had made him beloved was now his Achilles heel, pierced by the new era’s scorn. His cool restraint left us cold. Morality and patriotism bored us. The new kings—first Sinatra, then Elvis—were sexy and vulnerable, their voices charged with a raw emotion that bemused him.

“He has this tense Sicilian quality,” Crosby said of Sinatra, “while I don’t have any tenseness at all.” His gift was a relaxed one, pleasing the ear as he interpreted the nation’s musical history. He did not ooze bad-boy charm, and he was not about to spill anguish onto the stage, rip open a satin jumpsuit in a Dionysian frenzy, or thrust with sexual hunger. Pop music—which he had essentially invented—had begun packaging itself for postwar teens whose hormones and cash flowed freely. As backdrop, the nation was entering an era of therapy, celebrity confession, and reality TV. Dismissed by the young as uptight and out of touch, adults stood in the shadows humming old standards under their breath. Onstage, sex and rage dropped the mic.

Bing did not change. We did.

• • •

Bing Crosby in the movie Road to Morocco (1942) movie poster

I watch his old movies, listen to his old songs. God, yes, they are dated. Their America is as naïve and sentimental as teenage girls—used to be. Set against hiphop, his lyrics—so catchy in their day, all that swinging on stars and wrapping your troubles in dreams—could be nursery rhymes.

Yet he makes me nostalgic, for an era I never experienced. The absolute refusal to stress about anything, the innocent mischief and silly fun, the ability to take life lightly—Bing’s style feels like balm in this worried, workaholic world.

He was all about fun and leisure. Holiday Inn was one of his classics, along with all those goofy On the Road movies he made with Bob Hope. The first thing Fr. O’Malley does in The Bells of St. Mary’s is give the kids a holiday. And for decades Christmas was inextricable from Bing Crosby, that gentle, reverent voice rendering “Silent Night” and then the wistful “White Christmas.” He sang it every year on his Christmas special, which Giddins is convinced he only made for his second family’s sake.

Those specials ooze canned cheese, but somehow his low-key presence makes it palatable. I watch one after another, wincing at the overbright smiles, the kids with their memorized banter, Kathryn gliding across the set like the lady of the manor, Robert Goulet singing like a man in love with his own voice. Bing never fawns, freezes up, or tries too hard. Even with his elbows bent, doing that finger-snappy little dancewalk male singers used do to look lively, he has a jazz musician’s detachment from the bullshit.

Alas, his detachment stretched further. The only times he seems to be acting, rather than just being himself, are the times his character is scripted to be tender or passionate.

“He really was a very shy man, and he would put the love scenes off until the very last minute,” Mary Martin recalled. “And then he’d get on his bicycle and ride off as fast as he could.”

He and Ingrid Bergman had fun pranking the priest who was on set to make sure there was no hint of sexual attraction between Father O’Malley and Sister Benedict. One day they inserted a long, erotic gaze and passionate kiss into one of the takes and nearly gave him a heart attack. But while Bing “was very polite and nice,” Bergman said later, he spent most of his free time chattering with other guys.

Some of his biographers claim that women scared him, which is hard to credit of a man who bedded Grace Kelly. But both wives were nineteen when he fell for them, and both were deferential. When they married, Dixie was more famous than he—headlines read “Fox Star Dixie Lee Marries Singer” and “Well-Known Fox Movie Star Marries Bing Croveny,” who in another article was “Murray Crosey.” Dixie gave up her career to bear him four children. After her death, he started a second family with Kathryn Grant, an actress thirty years younger than he. She left acting to give him a second family, then got a nursing degree she used to tend to his health.

His love life had shown little imagination. One of his first loves, Peggy Bernier, rejected him. Dixie had been Peggy Bernier’s understudy, and Kathryn looked just like her. In between, his most intense affair was with Joan Caulfield—who looked just like Dixie.

After the affair ended, Caulfield announced that Bing had “a little bit of ice water for blood,” a description only slightly more complimentary than the pal who said he “pissed icewater.” Regardless which body fluid was blamed, Bing could chill a room. He once invited a gag writer to his summer home for a weekend and remarked, “I like you because you don’t ask me any questions.”

He said his emotional restraint was his mother’s—and he was not apologizing. Its imperative had soaked into his bones, making anything more open look sloppy or gushy or weak. “I may think a lot of a person, but I seldom tell them so,” he said. “I’ve never told a friend that ‘I love you’ or ‘I like you’ and if any friend told me that, I’d be very embarrassed and wouldn’t know what to do.”

One could argue that he was a product of his times—the days when White men called the shots and everyone else made excuses for them. But even by those standards, he was selfish. His charm lay in self-deprecation, not flattery of others. Even the characters he played were self-absorbed or solitary, cut off from intimate relationships. Many drank too much, as he had in his early years; many were performers who failed to show up, and he had done that, too.

After Dixie died, he could not bring himself to say he loved her; what he said instead was, “I’m going to sorely miss her love.” When Eddie Lang died, Bing put his head in the lap of Eddie’s young, bereft widow and wailed, “He was my best friend.” When Bing married Kathryn, his first words to her after the ceremony were, “Mrs. Crosby! How about that!” Their daughter, Mary Frances, later recalled, “If I kissed him goodnight, he’d pull away. If I hugged him too long, he’d squirm.”

Crosby could barely spit out a compliment, especially to his own kids. Yet when he shared the stage with another performer, he went out of his way to relax them. “We’re going to have fun with this,” he told his thirteen-year-old co-star in If I Had My Way. “Throw it away and don’t try to act.” When young singers were scared, he stayed on stage with them, sometimes literally holding their hands until they found their confidence. If somebody made a mistake while filming or recording, he covered for them, saying, “I think I messed that up a little. Can you do it again?” He kept a list of friends his accountant should automatically help out whenever they were in need. When Peggy Lee’s husband fell ill, she said Bing “offered everything—money, cars, his own blood, and even volunteered to baby sit with our little daughter.”

Is “selfish” too harsh, then? He locked his deepest feelings inside. The result was a pleasant life, but not necessarily a happy one. And it was certainly not the life his audiences had imagined.

• • •

In March 1977, Bing did a television special, celebrating his fiftieth anniversary in show business. Bob Hope introduced him—as “the orange juice junkie.” His son Nathaniel teased him on camera: “You could sing something a little contemporary.”

He tried, but the next number went right back to his comfort zone. “Let me reach into the smoldering embers to pluck out a few old chestnuts,” he begged, launching into, “You got to accentuate the positive, eliminate the negative.” People smiled, not realizing those lyrics were his formula for warding off emotional chaos.

Only after his death would we realize just how much chaos he had suppressed.

That fall, Bing abruptly made a public statement. “It is alleged by some careless people that I am a loner, a cold fish without sentiment or convivial instincts,” he began, then explained that he was simply “not very demonstrative. I don’t gush, wring my hands or beat my bosom.” He listed off the many different sorts of people he knew. Then he segued into cultural critique, bemoaning all the porn, nudity, and irresponsibility before saying, “One ray of hope that I see on the horizon is the increasing interest in nostalgia.”

The man who had embraced each new technology, each new medium, each genre of song, could not inhabit a culture that, in the idiom of the time, “let it all hang out.”

Just days later, on October 14, 1977, he played golf in Madrid. He was paired with a Spanish champion, and they won. “That was a great game of golf, fellas,” he said. “Let’s go have a Coca-Cola.” A minute later, a heart attack, sudden and strong as an earthquake, knocked him to the ground.

His death made front pages all over the world, the headlines as bold as a war declaration: “Bing Crosby Dies.” Bob Hope canceled a concert, something he had never, ever done. President Jimmy Carter praised Crosby for remaining a gentleman despite the pressures of show business, adding that “he lived a life his fans around the world felt was typically American: successful yet modest; casual but elegant.”

Death reminded people how much they had loved Bing Crosby, how his singing had soothed them. So many records were sold that Decca had to lease pressing plants from other companies to keep up. But then came the books. A biography called Bing Crosby: The Hollow Man savaged him, painting a picture of a mean-spirited egomaniac incapable of love or loyalty. Hollywood had protected him, the authors said, implying secrets far darker than the evidence suggested. So did Going My Own Way, written by his firstborn, Gary Crosby. His father had been not just stern but abusive, Gary told the world.

That fast, Bing Crosby became just another fraud. Cynical young people who had only seen him on his orange-juice commercials decided that their parents had been fooled yet again. This laidback nice guy whose life was supposedly an open book was secretly a mean, selfish bastard.

Was it that simple?

The 2022 commemorative edition of Bing Crosby’s 1977 televised Christmas duets with David Bowie.

Hollywood did protect him, and so did the media. “There had been the strangest conspiracy among even the gossip columnists to protect Bing and Dixie,” wrote a Los Angeles Mirror columnist after his death. But that had more to do with the tragedy of Dixie than any villainy of Bing’s.

Gary softened later, said he came to realize his father really had loved them. But the intimations of abuse stuck in the public mind. This was more than sanding off Hollywood lacquer. This deception was unforgivable, because it hurt.

Bing Crosby’s plummet from fond memory was caused by his character and by the country’s climate, because for decades, the two were inextricable. A man’s man at a time when that was a compliment, he remained emotionally closed in the years when the entire nation was emotionally closed. But he got stuck there. His way was the old American way—something we can no longer even agree on, let alone be smug about. Nor can we find a single set of standards by which to judge our idols; even values are niche now. The mass culture that held us together—and gave Bing Crosby his vast fan base—is gone.

He had flawless musical timing, comic timing, cultural timing. When he fell out of time, we sped away from him. We still say Satchmo’s name, Ella’s, Sinatra’s, Elvis’s, with reverence. But only a smattering of fans and jazz musicians invoke “Bing Crosby” with similar awe. The fans are, most of them, members of the venerable International Club Crosby, which made the Guinness World Records as the oldest fan club in history, yet which few now join.

Dr. Anton Garcia-Fernandez, the American co-editor of the ICC’s BING Magazine, says “people remember Sinatra, the Beatles, and Elvis better. But that has a lot to do with marketing strategies. Sinatra’s family is keeping his legacy alive. And look at Graceland.”

Look, too, at Bing himself. Refusing any real vulnerability, he perfected the art of self-deprecation—the sort that pushes people away without secretly hoping to be contradicted.

In the end, we believed him.

Read more by Jeannette Cooperman here.