Legendary singer Tony Bennett brought early American songs to life

He won 20 Grammy Awards and performed with dozens of other artists over a remarkable 7-decade career

Today's expression: Give way
Explore more: Lesson #597
August 10, 2023:

Antonio Dominick Benedetto--later 'Tony Bennett'--had one of the great American entertainment careers. Born in Queens, New York, he rose to fame by singing early American jazz and musical songs. His most famous song was "I Left My Heart in San Francisco." But the peak of his popularity came just as rock-and-roll music arrived in America. Plus, learn the phrasal verb "give way."

Be your best self in English

Move confidently through the English-speaking world

Listen

  • Learning speed
  • Full speed

Learn

TranscriptActivitiesDig deeperYour turn
No translationsEspañol中文FrançaisPortuguês日本語ItalianoDeutschTürkçePolski

Tony Bennett had one of the great American careers in entertainment—today, we’ll take a look back at the iconic singer’s career.

Lesson summary

Hi there everyone, I’m Jeff and this is Plain English, where we help you upgrade your English with stories about current events and trending topics. This is lesson 597, so you can find the full lesson online at PlainEnglish.com/597.

Coming up today: When someone has a “second act,” they find success for a second time in their career, usually after suffering through a slump. Steve Jobs is a great example. He co-founded Apple Computer in 1976. He was fired from the company he founded in 1985. After eleven years, though, Apple hired him back and he led the company—and the world—into the smartphone era with the iPhone. That was his second act.

Well Tony Bennett had a second act, and it was one of the great second acts in all of entertainment. Tony Bennett died on July 21 this year, just a few days shy of his 97th birthday. We’ll talk about Tony Bennett’s remarkable career today and we’ll continue it on Monday. You know I like to say, you’re learning English, so you should know about the English-speaking world. Tony Bennett was a giant in American music culture, and he is well, well worth learning about.

In the second half of today’s audio lesson, we’ll talk about the English expression “give way.” And we have a song of the week from Tony Bennett himself.

Tony Bennett and the ‘Great American Songbook’

“The Great American Songbook” is a genre of music that was written for the stage, musical theater, and Hollywood in the early Twentieth Century, roughly from the 1920s to the 1960s. These are classic jazz standards and show tunes that stood the test of time , they were popular in a variety of settings and for a long time. The name is a little deceptive, since there isn’t a book. But the genre includes songs written by Irving Berlin, George Gershwin, Cole Porter, and others.

This was the music that Tony Bennett sang over his remarkable seven-decade singing career. They’re songs like “The Way You Look Tonight,” “Rags to Riches,” and “The Best is Yet to Come.” You might not recognize those songs today, but I guarantee that some of your favorite English-speaking singers do recognize them.

Tony Bennett started singing these classics as an opening act for other musicians; then, he became a star in his own right; he suffered a slump during the advent of rock-and-roll; and then he pulled off a stunning second act that saw him perform with contemporary artists as varied as Elton John and Amy Winehouse.

He was born Antonio Dominick Benedetto in Astoria, a working-class neighborhood of Queens in New York City. His father came to America from Italy as a seven-year-old; his mother was born in the States, having crossed the Atlantic in the womb. As a child, Antonio found an early interest in singing and painting. At just ten years old, he sang at the inauguration of the Tri-borough Bridge in New York City, a massive bridge that connects three of the city’s five boroughs. Then-mayor Fiorella LaGuardia patted him on the head.

As a young man, Benedetto was drafted to serve in World War II. He was shipped off to fight in Europe, right as the war was reaching its end. He later described the experience as “a front-row seat in hell.”

While in service there, he was among the first soldiers to discover, and liberate, the concentration camps. Upon returning to the States, he took advantage of the GI Bill—government support for soldiers to go to college. He studied music and theater. He began singing in nightclubs.

His big break came in 1949. He was the opening act for another singer, Pearl Bailey. In the audience that night was Bob Hope, a larger-than-life comedian and celebrity. Bob Hope liked what he heard from Benedetto, and he said he wanted the two to perform together in the future.

Just one problem: “Antonio Dominick Benedetto” wasn’t the name of a performer—at least not an American one. And so he told Antonio that he would, from that moment on, be known as Tony Bennett. That was good advice from Leslie Townes Hope, a superstar who had shortened his own name years earlier.

“Tony Bennett” started performing with Bob Hope. But soon, Bennett himself became the star attraction: police had to put up barricades to hold back the crowds of people trying to get into his concerts. He started recording his own music—his first hit was “Boulevard of Broken Dreams,” released in 1950. He followed that up with other hits like “Cold, Cold Heart” and “Rags to Riches.”

He played on the first-ever episode of “The Tonight Show starring Johnny Carson” in 1962. Tony Bennett became the hottest ticket in New York, Los Angeles, and Las Vegas.

In the early 1960s, he was riding high. His pianist brought him a song he thought Bennett would like. It was called, “I Left My Heart in San Francisco.” Bennett performed it for the first time in—where else?—San Francisco. He then recorded it and released it on a B-side. That was the opposite side of a vinyl record, the side where you just put an extra song that you didn’t think would be very popular. But it turned out to be his biggest-ever hit. He won two Grammys for “I Left My Heart in San Francisco.”

Riding the strength of “San Francisco,” he was invited to perform at Carnegie Hall in New York City. It’s New York City’s most famous music venue. The show was a smashing success , receiving almost unanimous critical acclaim.

But in the late 1960s, as the early classics gave way to rock-and-roll, Tony Bennett’s career slumped. The Beatles played the Hollywood Bowl in front of thousands of delirious, screaming fans. The Rolling Stones exuded a bad-boy sexuality. Tony Bennett songs like “Cheek to cheek”, which romanticized a polite slow dancing, well, those seemed less and less relevant.

Little did anyone know at the time, though, that this singer of the classics wasn’t even halfway through his career. He still had his second act in front of him.

This is where we’ll pause our story for today. We’ll resume it on Monday, when we’ll talk about Tony Bennett’s second act.


Just to give you an idea of the range and influence Tony Bennett had in his career—and you’ll hear more about this on Monday—but he worked with and performed with musical artists of every type. Miles Davis, Count Basie, Natalie Cole, Elvis Costello and Aretha Franklin from the jazz era. From folk and country, James Taylor, Willie Nelson. From rock and roll, Paul McCartney, Elton John, Billy Joel, Bono, Sting. Classic singers like Barbra Streisand and Celine Dion. From country, Tim McGraw, the Dixie Chicks, Carrie Underwood. From more modern pop music, Mariah Cary, kd lang, Diana Krall, Lady Gaga. The list goes on.

So that’s why I say, you may never have heard the name Tony Bennett or heard any one of the songs he sang. But I guarantee a lot of your favorite English-speaking singers absolutely heard them, and may have even performed with Tony Bennett.

JR’s song of the week

JR has given me permission to select the song of the week this week, and I am going to select my favorite song from Tony Bennett’s catalog. It’s “The Way You Look Tonight.” This is a perfect example of a Tony Bennett song—he didn’t write it. He didn’t write his songs. This song was written in 1936 for a movie called “Swing Time.” The famous early actor Fred Astaire performed it in the movie.

Like many songs from that time, the song doesn’t seem to belong to any one artist. Bing Crosby sang this song, Frank Sinatra did, Michael Bublé did.

Tony Bennett first recorded “The Way You Look Tonight” in 1958. And he released another in 1997 for the movie “My Best Friend’s Wedding.” And he released a duet with Faith Hill in 2011.

And that’s the version that we’ll pick as the song of the week—we’ll put a link to it in the lesson email and in Instagram stories. “The Way You Look Tonight,” the duet between Tony Bennett and Faith Hill is the song of the week.

All right, enough music for now—let’s pivot to an English expression. Today, it’s “Give way.”

Learn English the way it’s really spoken

Starter feature

We speak your language

Learn English words faster with instant, built-in translations of key words into your language

Starter feature

We speak your language

Learn English words faster with instant, built-in translations of key words into your language

Starter feature

We speak your language

Learn English words faster with instant, built-in translations of key words into your language

Starter feature

We speak your language

Learn English words faster with instant, built-in translations of key words into your language

Starter feature

We speak your language

Learn English words faster with instant, built-in translations of key words into your language

Starter feature

We speak your language

Learn English words faster with instant, built-in translations of key words into your language

Starter feature

We speak your language

Learn English words faster with instant, built-in translations of key words into your language

Starter feature

We speak your language

Learn English words faster with instant, built-in translations of key words into your language

Starter feature

We speak your language

Learn English words faster with instant, built-in translations of key words into your language

QuizListeningPronunciationVocabularyGrammar

Free Member Content

Join free to unlock this feature

Get more from Plain English with a free membership


Starter feature

Test your listening skills

Make sure you’re hearing every word. Listen to an audio clip, write what you hear, and get immediate feedback


Starter feature

Upgrade your pronunciation

Record your voice, listen to yourself, and compare your pronunciation to a native speaker’s

Starter feature

Sharpen your listening

Drag the words into the correct spot in this interactive exercise based on the Plain English story you just heard


Starter feature

Improve your grammar

Practice choosing the right verb tense and preposition based on real-life situations



Free Member Content

Join free to unlock this feature

Get more from Plain English with a free membership

Plus+ feature

Practice sharing your opinion

Get involved in this story by sharing your opinion and discussing the topic with others

Expression: Give way