I’m a fan of Bing Crosby’s artistry every day of the year, and not just when he returns to the airwaves at Christmas time. But the holiday spirit inspires me to celebrate some of my favorite moments in his remarkable career—which took him from Bix to Bowie and beyond—in this story from my archives.

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Now let’s turn to Bing….

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Four Perspectives on Bing Crosby

Pop culture devours its own. The destiny of all bestsellers is to fall off the charts. Even the stars in Hollywood, like those in outer space, eventually stop shining—and it happens a lot sooner.

Consider the case of Bing Crosby. Some of my readers might not even recognize the name. But a few people still alive today can recall when Crosby was both the biggest pop singer in the world and the hottest movie star in Hollywood.

If he’s remembered nowadays, it’s only during December, when his version of “White Christmas” briefly returns to heavy rotation. Even today, it ranks as the bestselling single of all time. There aren’t many records that last eighty years, and least of all in the record business, but Crosby still sits atop this chart.

Here it is (courtesy of Wikipedia):

I’ve written about Crosby before, and will again. But today I want share four of my favorite (and very different) perspectives on Bing.

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1.

In June 1945, a US military commander in the European campaign wanted to write to Bing Crosby—to tell him how much the singer contributed to troop morale during World War II. 

He had no way of reaching Crosby, so he simply addressed the letter as follows:

Mr. Bing Crosby
Wherever You Are
c/o Postmaster
New York, NY

Somehow the letter arrived at its intended destination—we know that because it survives, with a handwritten addendum from Crosby himself on top of the page, where Bing jotted “nice letter.”

Indeed, it was. I want to call attention to it because it gives a completely different angle on Crosby’s exceptionally laid-back and low-key demeanor—which you might think has nothing in common with a soldier’s day-to-day burdens. It also testifies to powers of music we’ve too often forgotten in the present day, to our detriment.

The full letter is unpublished. But in the second volume of his Bing Crosby biography, Gary Giddins shares some details. The commander, from his camp in Antwerp, wrote

of that ‘quality in your voice which strikes to the bottom of the hearts of men. I have watched it happen, often, not just in the rare case but in many many thousands of men — sitting silent, retrospective, thoughts flying back to home and loved ones.’ He emphasized the singer's ‘power to soften the heart of the man who so shortly after goes back to shoot down his brother man,’ saying it was a determinant in helping to keep ‘our boys from turning into the beasts they are asked to be.’

This, he said, was ‘something big, something too big not to have you know and understand’ — the ‘power of music, put into humble, throbbing words, as these fellows want it, need it, bow to it.’

That may be the most moving testimony to the power of a pop singer I’ve ever read. In the midst of the most savage war of the century, Bing Crosby was a touchstone of decency and humanity for the troops on the front line.

2.

I can’t validate this next story, because I heard it secondhand or third-hand years ago, but it’s too good not to share.

The story involves Bing Crosby in the final years of his life. He was invited to sing at an event, probably for a charity or cause, and the host enlisted some young progressive jazz musicians to accompany the famous singer. The band members weren’t impressed by this aging star, who had made his reputation back in the 1920s, and decided to throw Crosby off his game.

When Bing showed up, he greeted them in his typical laidback manner, and told them he would sing some familiar old songs. But when the performance started, these young jazz players threw in every arcane substitute chord change and rhythmic displacement they could think of, further spicing up their accompaniment with Coltrane modal fills and bits of polytonality.

Much to their frustration, nothing they did that evening disrupted Bing in the least. This old, balding pop singer navigated effortlessly through every one of their advanced harmonies, never faltering or showing the slightest degree of discomfort. Even more infuriating, Bing maintained the relaxed and unflappable delivery that was a Crosby trademark. As far as the audience could tell, he was just as happy-go-lucky as ever, and maybe he was—after all, Crosby had learned the ropes as a young man alongside Bix Beiderbecke, who was as unconventional and unpredictable as any musician from the early 20th century

When the performance was all done, the musicians expected to get chewed out by Crosby backstage. Instead, Bing shook their hands, and thanked them with great warmth. He said how “cool it was to play with these young cats,” and expressed his sincere desire that they might do so again in the future.  

3.

At some point, I plan to publish an in-depth account of how Bing Crosby helped create Silicon Valley. In the meantime, here’s an extract:

Bing Crosby felt exhausted in the mid-1940s. And who could blame him? He was the most popular musician in the world—and it wasn’t just “White Christmas,” which sold more records than any other song in history. He eventually recorded some 1,600 songs, and more than forty of them reached the top of the chart. But he was just as popular in movies, winning the Oscar for Best Actor in 1944, and getting nominated again in 1945. In addition, he was tireless in touring and entertaining troops during the war.

But it was his radio show that proved too much. Because of the time difference, he had to do two different live broadcasts—and the network refused his proposal that they pre-record the later West Coast show on 16-inch transcription disks, basically a very large phonograph record. NBC had good reason for this. The sound quality on the disk recordings of that day were noticeably inferior. And the disks were cumbersome to edit—negating one of the major advantages of pre-recorded shows.

Crosby needed better recording technology. And in 1947, a stranger from Northern California made the trek to Hollywood with a big box that not only solved Bing’s dilemma, but set the wheels in motion for a whole host of later technologies.

What Jack Mullin did at MGM Studio that day is almost like a magic trick. He set up a live performance behind a curtain, and then followed it with a playback from his magnetic tape recorder. The audio quality was so true-to-life that many listeners couldn’t tell the difference. A private demonstration was arranged for Crosby at the ABC Studio on Sunset and Vine.

Crosby knew this was a huge breakthrough. But the price of a single Ampex 200-A recording machine was $4,000—more than many people paid for a home back then. In fact, the average median family income in the US that year was just $3,000. But Crosby wanted to buy 20 of these devices. He offered to pay 60% of the money up-front.

Thus, a few days later, a letter arrived in the Ampex office with a Hollywood postmark. Inside was a check from Bing Crosby for $50,000.

Ampex, according to Silicon Valley historians Peter Hammar and Bob Wilson, was later involved either directly or indirectly in the launch of “almost every computer magnetic and optical disc recording system, including hard drives, floppy discs, high-density recorders, and RFID devices.”

In other words, Bing Crosby launched the data storage business in Silicon Valley—indirectly laying the groundwork for everything from computer hard drives to cloud computing.

4.

You could also use Bing Crosby as a case study in partnerships.

Superstars tend to be lone wolves. Even if they rise to fame as part of a band, the team frequently breaks up and stars go their separate ways. That’s true of all four Beatles, Michael Jackson, Diana Ross, Beyoncé, Phil Collins, Justin Timberlake, and several hundred other hitmakers.

Gilbert and Sullivan broke up after arguing over the cost of a carpet. The Dorsey brothers separated after disagreeing on the tempo of a song. Simon & Garfunkel broke up over . . . . well, that depends on which of their breakups you’re talking about. They found about 50 ways to leave their partner.

But Bing seemed to work effortlessly with other superstars without egos getting in the way. That was true from the start, when he learned from jazz legend Bix Beiderbecke. And years later he happily share the stage and movie screen with everyone from Louis Armstrong to Frank Sinatra. And late in life, he amazed rock fans by singing alongside David Bowie.

Many think that was Bing’s most unusual collaboration, but I would opt for this one (which I found on Twitter):

When you watch Bing with other superstars, you never detect even a sniff of competition or one-upmanship. I’m convinced that Bing’s adherence to the cool ethos is part of this—going with the flow was a Crosby trademark.

The most famous example is Crosby’s lifelong partnership with Bob Hope—who was not anywhere near as easygoing as Bing. Crosby was already a superstar when he first enlisted Hope to serve as emcee for a 1933 show. Eventually Hope rose to the top of the Hollywood hierarchy as the most popular comedian in the US, but Crosby never showed any signs of rivalry (although their onstage skits frequently pretended at it).

They made seven “road” pictures together, and grew closer with each one. By the time Crosby and Hope did Road to Hong Kong (1962), they actually decided to bring their wives along for the London filming, and shared a house together. “Bob’s wife, Dolores, said that was when they first realized how much they really loved each other,” explains Hope’s biographer Richard Zoglin.

One of my personal movie regrets is that Hope’s plan to make a final film with his friend never happened. Hope tried to secure adaptation rights of Neil Simon’s The Sunshine Boys, a story about two aging comedians, but got turned down. Otherwise, that movie would have served as a lovely capstone to a forty-year-plus partnership. Instead, the movie came out in 1975 starring George Burns and Walter Matthau—both remarkable comedians but without anywhere near the chemistry of Bob and Bing.

Abbott and Costello couldn’t match that longevity, and fell apart because of bickering after 22 years. Martin and Lewis broke up after exactly ten years together. Sonny and Cher got to eleven years before divorce ended their music-and-comedy success. Louis Prima and Keely Smith, who had a very similar husband-and-wife routine, only lasted nine years before they split up.

But Crosby and Hope were lifers. They joked about their schemes to upstage each other, but the reality was the exact opposite. If you haven’t seen any of the movies they made together—and you don’t have much of a chance nowadays, because Netflix doesn’t care about the history of cinema—find time to do so. You won’t be disappointed.

Two years after The Sunshine Boys, Bing Crosby left us at age 74. This master of relaxed understatement actually died on the golf course after saying these final words: "That was a great game of golf, fellas. Let's go have a Coca-Cola.”

The only time Bob Hope ever cancelled a performance was after his onscreen partner’s death. “If friends could have been made for each other,” he explained, “I would have asked for one just like Bing.”

So when you hear “White Christmas,” let it serve as a reminder of what cool is really all about. Bing’s unflappable, amicable demeanor and collaborative spirit—emblematic of coolness and jazz, in my opinion—ought to be as much of a legacy as all those hit songs. We could certainly use a dose of them every year, and (dare I say?) not just in December.