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The Perfect Beat: Tony Bennett’s “How Do You Keep the Music Playing”

“The Perfect Beat” is The Flyover’s ongoing series discussing our favorite moments in the history of recorded music. 

Today, we honor the birthday boy: Mr. Tony Bennett


The Artist

One could argue that every note Tony Bennett has ever sung could qualify for “The Perfect Beat.” He recorded his first single, the incredible “Boulevard of Broken Dreams,” in 1950, and earlier this year was still performing at the highest level to sold out crowds around the world. He is a living legend, respected and adored by fellow artists and fans young and old.

Anthony Dominick Bennedetto was born in Queens in 1926, the son of a grocer and a seamstress. Growing up in poverty during the Depression, he immersed himself in the arts, soon performing at the unveiling of the Triborough Bridge at just ten years old. Let that sink in for a second: Tony Bennett has been singing professionally for 84 years.

After studying his idols Bing Crosby and Louis Armstrong, as well as proper technique to go along with his perfect pitch, Bennett served his country as an infantry rifleman during the final year of World War II, helping liberate a concentration camp near Landsberg, Germany. It was perhaps this experience, as well as the intense discrimination he and his immigrant Italian parents suffered in the early part of the century, that became his window into the pain and suffering of others.

He would look through this window often, not just as he honed his craft to deliver the wondrous, emotional interpretations of the classic songs of his youth, but also as he championed the rights of others, later becoming an important advocate in the Civil Rights movement.

His impressive musical output, now spanning more than eight decades, is matched only by the beauty and generosity of his spirit. In 1999, he established the Exploring the Arts Foundation, to him an accomplishment as great as Frank Sinatra calling him “the best singer in the business.”

When you listen to his songs or see him perform, it’s impossible not to agree with The Chairman’s praise. But, it’s a song on his 1986 comeback album, “The Art of Excellence,” that contains one of his greatest recorded achievements.


The Song

By the mid-1970s, Tony Bennett was already a legend. He had recorded a mountain of hits, sang alongside his heroes, and was performing concerts to adoring fans all over the world. However, nine years would go by between his last album of the 1970s and his first album of the 1980s, a gap that saw Bennett lose himself in a surprising, disturbing fog of drug use.

By 1986, Bennett was clean, clear, and focused, ready to reach the mountaintop he had once etched his name in. His comeback album was to be called “The Art of Excellence,” a new mission statement filled with the kind of hubris only a true great would dare claim. While the album’s cover displayed an aging man desperately trying to appear hip, the songs within were as good as anything he’d ever recorded, perhaps none better than the newly-penned “How Do You Keep the Music Playing.”

The narrator begins the song worrying about the realistic possibility of true, long lasting love:

How do you keep the music playing?
How do you make it last?
How do you keep the song from fading too fast?

How do you lose yourself to someone
And never lose your way?
How do you not run out of new things to say?

This is not the man once brimming with confidence and charisma like the Tony Bennett of the 1950s, nor the one who could make you cry with style and swagger like he did in the 1960s. No, this man is aching, questioning whether or not he’s got what true love takes:

And since we know we’re always changing
Why should it be the same
And tell me how year after year
You’re sure your heart will fall apart
Each time you hear the name?

It’s a shocking display of exposed sadness, just a singer and his aching emotions laying themselves bare to the listener:

The more I love the more that I’m afraid
That in her eyes I may not see forever 

On its surface, it’s a song about love and relationships. But, like any great story, it also serves as an allegory for the previous decade of Bennett’s life. His voice, once so confident, now reveals itself to us in the most delicate offering of his deepest confession.

In some ways, it’s the type of performance that embodies the punk spirit of the music that forced him into early retirement in the late-70s and early 1980s, a sort of crooning “Nebraska.” It also foreshadows the music of the 2000s that would ultimately help connect him with new audiences and cement his legacy and staying power.

In a word, it’s real. Authentic. 


The Moment

After two-and-a-half minutes of worry and despair, Bennett collects himself. He sings:

If we can be the best of lovers
Yet be the best of friends
If we can try with everyday to make it better as it grows
With any luck, then I suppose…

It could just as easily be words spoken to a lover as it could a promise to his audience: I know I’ve made mistakes and have had my doubts, but I’m dedicating myself to you from here on out. 

And as he makes this vow, at age 60, he sings the song’s final words in the most stunning vocal you’ll ever hear on record:

The music never, never, never ends


Why It’s Perfect

Just listen to it.

It’s in this moment that Bennett delivers on the promise of the album’s title: excellence. It’s a note that summons the previous three minutes, and past decade, of despair, willing them into confidence through sheer force. He repeats “the music,” and stretches out “never, never,” in an unbelievable display across several octaves, at once declaring his undying love and emphatically cementing that promise.

It is simply without equal. Bennett’s incredible command and range, then in its seventh decade, demand you to listen and believe him. In just a few seconds, he turns the narrator from a down-on-his-luck Sinatra character into the champion of the world. And when Sinatra attempted the song a few years later, he didn’t even try to match Bennett’s intensity; instead, he sings the final line as if a lament, robbing the song of its force and value.

It’s perfect because it has always been my wife’s favorite song, and perhaps speaks to why she always saw more of me than I ever could in myself. 

To me, the song summed up a lot of my own fears as I wrestled with the idea of marriage. I could identify very strongly with the character in the first few verses, unsure less of my partner than of myself. What if I’m not up to it? What if we change? What if true love is a lie? What if forever is too long of a time? How do you keep the music playing?

And in the final moment of this brilliant song, as much in emotion as in words, Tony Bennett, as he always has, shows us the way.

Bonus: Tony Bennett "True Blue Lou" (1963)

As we celebrate Tony Bennett’s life and music for his 94th birthday, I wanted to share a quick example of what made him so great, particularly during his prime.

This is Tony Bennett at his most casual cool, something you’d associate a little more with the Frank Sinatra of this era than the more humble Mr. Bennett. As the song begins, performed incredibly by his trusty Ralph Sharon Trio, Bennett does something that Ol’ Blue Eyes could only have wished.

Listen to the very first three words of the song: “True. Blue. Lou.” Watch his hands as he sings. “True. Blue. Lou.” Watch the charismatic little smile afterwards. You probably already feel something just listening to those first three words. “True. Blue. Lou.” You feel it and you don’t even know why. “True. Blue. Lou.” But, what’s so special about someone singing three words? 

In this brief moment, Bennett accomplishes something that very few singers would even dare: he swings quarter notes. Swing. Emotion. Charisma. Listen to it again. “True. Blue. Lou.” It says everything you need to know about the singer, the song, and whoever this Lou guy is in just three, swingin’ notes.

“True. Blue. Lou.”

Happy Birthday to an absolute legend, Mr. Tony Bennett. The best is yet to come!

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