ho’s better: Bing Crosby or Frank Sinatra?

Fans of Crosby and Sinatra have a lot in common. They’re nostalgic, sentimental, old (or, if young, going to be old soon enough), and most of all, they share the conviction that their favorite is the greatest popular singer of the 20th century.

In regard to the last point, the Sinatra fans are wrong.

Most writers comparing the relative merits of Crosby and Sinatra are going to be tempted to make some cheap shots. I am one of those writers. Crosby didn’t fawn over the Kennedys, get publicly rejected by Ava Gardner or drunkenly provoke Harlan Ellison and Mike Royko. Crosby’s duet with his son Gary (“Play a Simple Melody”) is great; Sinatra’s duet with daughter Nancy (“Somethin’ Stupid”) is self-fulfilling prophecy.

But is it really worth the time to attack Sinatra for his personal behavior when his recorded output provides so many ample targets?

Sinatra was not intelligent enough to learn the value of subtlety. He poured his heart out into melodramatic recordings like “In the Wee Small Hours of the Morning,” “Guess I’ll Hang My Tears Out to Dry,” “Glad to be Unhappy” and “Angel Eyes.” He sang without restraint, without embarrassment, without self-consciousness – in short, without intelligence or dignity: the perfect entertainer for the American people.

The first impression most people have of Crosby is of a pleasant, rich voice that sounds deceptively easy to imitate – a voice that seems so effortless in its intonation that listeners have accused him of actually muting song lyrics, rendering them inert and listless.

Of course, nothing could be further from the truth. Crosby, an extraordinarily intelligent man, knew that indifference is a more effective weapon in affairs of the heart than passion – regardless of whether the love is requited.

In Crosby’s recording of “Thanks for the Memory,” a first listening exudes only good-natured sentiment. It takes subsequent listenings to reveal the brilliant cruelty in Crosby’s method. As he nears the end of the song, reaching lyrics that discuss the parting of lovers, his enunciation becomes slightly more clipped, more dry. The sarcasm in his reading of the lyric “no tears, no fuss / hooray for us” is subtle, but unmistakable. It’s the intonation of a man who’s so far past caring about his former lover that he’s perfectly willing to let his real indifference show through. His love has faded to the point where he can be maliciously sarcastic to his ex.

Aggression, despair and rapture, the trademarks of Sinatra’s relentlessly heart-on-the-sleeve style, are obviously beneath Crosby. And, at risk of attaching too fine a point, it’s because Crosby is better than Sinatra.

Crosby’s phenomenal popularity makes ours a more interesting country, because it is extraordinary that his bleak, nihilistic evocation of human relationships was able to find such popular favor with the American people.

Crosby was Machiavellian and sadistic, and he makes us all a little more Machiavellian and sadistic each time we listen to him.

Play the best of Crosby’s recordings – “A Long, Long Time,” “Galway Bay,” “It’s Easy to Remember” and “Who’s Sorry Now?” – back to back with Sinatra's versions and one can fully appreciate Crosby for the genius he was. And Sinatra for a blustering, narcissistic, self-aggrandizing, comically melodramatic goon.