Bing Crosby and The Intimacy of Crooning: Creative People Can Make Great Entrepreneurs


Bing Crosby was a revolutionary. 

Born in Takoma, Washington in 1903 and raised in Spokane in the same state, he embarked on a musical career in the 1920s when the convention amongst singers was to deploy a loud ‘belting’ sound. Performers like Al Jolson from the vaudeville tradition were ever mindful of the need to project their big, booming voices to the back seats of the theatre. 

Crosby was one of a new generation who embraced the recent technology of the condenser microphone. He regarded the microphone as his instrument. He leaned into it, caressed his notes and purred his lyrics. With the microphone he could bend melodies and twist phrases. He could be laid back and conversational, pleading and emotional. He could be intimate.

Though Crosby didn’t like the term, the new singing style was called ‘crooning.’ Some were critical of this fashionable approach. Cardinal O’Connell of Boston complained: 

‘Crooning is a degenerate form of singing…. No true American would practice this base art. I cannot turn the dial without getting these whiners and bleaters defiling the air and crying vapid words to impossible tunes.’

Nonetheless, crooning was a hugely popular phenomenon. Ten of the Top 50 records of 1931 featured Crosby’s mellifluous bass-baritone. Crooning was informal, easygoing, casual. It seemed quintessentially modern and American. The key to its appeal resided in its intimacy. The crooner came across as someone who was in the room with you, sharing a joke or confiding a secret; as someone you knew. Fellow singer Dinah Shore observed: 

‘Bing Crosby sings like all people think they sing in the shower.’ 

Perhaps there’s something we in the field of commercial creativity could learn from Crosby. We tend to concentrate on the functional benefits of digital technology: we think of it in terms of enhanced data, distribution and targeting; of superior user interfaces, connectivity and customer journeys. Of course, technology delivers all these things. But we should not forget its considerable emotive power: technology can demolish distance and time; it can create closeness; it can make things more personal and private. Technology enables human intimacy. This is a precious thing.

Crosby went on to become the world’s first multi-media star. His success extended from live performance, to radio and recordings. He had an Oscar-winning film career and he later evolved into TV. 

‘Listen a lot and talk less. You can’t learn anything when you’re talking.’

Throughout his life Crosby was a natural innovator. When the record market was hit by the Depression of the 1930s, he agreed to take a royalty rather than the customary flat fee. In the 1940s he embraced magnetic tape and was the first major performer to pre-record his radio shows. With pre-recording he could control performance conditions and times; he could ad lib and edit out mistakes. And by pre-recording four shows in a week, he could also spend more time on the golf course. 

As his fortune increased, Crosby bought TV stations and recording studios. He financed the development of the video-tape. He invested in fast-freezing technology and became Chairman and lead promoter of Minute Maid orange juice.

We can learn a great deal from Crosby. He demonstrated that creative people should view technology, not as an enemy, but as an ally - something that inspires new approaches and opportunities; something that enables them to take control of their work and how it is received. And critically he demonstrated that creative people should regard entrepreneurism, not as an alien craft, but as a natural extension of their talents. Creatives should be at the heart of a thriving business, not at the margins of it.

Bing Crosby passed away in 1977, having completed a round of golf on a course outside Madrid. His last words were:

‘That was a great game of golf, fellas.’


‘Oh, what eyes you have.
Oh, what lips you have.
Oh, what lovely features.
Talk about adorable creatures.
You have so many thrillables,
That I’m all out of syllables.
From the top of your head,
To the tip of your toes,
You’re marvellous.
Glorious, you are simply divine.
Top to tip, you’re tip top,
But to top it all, you’re mine.’

Bing Crosby, From the Top of Your Head (Mack Gordon, Harry Revel) from the film Two for Tonight (1935)

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