When you think about the classic songs of American big band music or jazz, there’s a good chance that you’re thinking of at least one song performed by Tony Bennett. Here, we look back at the legend's life.
1. He Used A Stage Name
Anthony Dominick Benedetto was born in New York City’s district of Queens on August 3, 1926. He was the youngest child of a grocer named John Benedetto and a seamstress named Anna Suraci. Yet these humble beginnings weren't enough to stop Bennett's passion for song...and soon he was surprising everyone.
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2. He Was Precocious
By age 10, Bennett was already gaining attention with his singing voice. He got a big break. The young Bennett went to the opening of Triborough Bridge to sing as part of the ceremony. In a famous anecdote, Bennett sang while standing next to New York's mayor and received a pat on the head from him in appreciation.
But that was just the beginning.
3. He Hit The Streets
Bennett didn't stop at bridge ceremonies, and first started singing for money when he was barely a teenager. His stages were the various Italian restaurants in his home neighborhood, where he was also working as a waiter during that time. That's how determined he was to make it in the world.
Still, he quickly found out that the world could also be cruel.
4. He Lost His Father Young
To the music world, Tony Bennett was like a father—but he got precious little time with his own dad. Bennett’s father, John, was responsible for instilling a passion for art, but the elder Benedetto was also frequently ill. It led to tragedy. He passed when Bennett as just 10 years old. And then it got so much worse.
5. He Grew Up Fast
The illness and premature passing of Bennett’s father wasn't just emotionally difficult, it also put an enormous financial burden on the Benedetto family. They were now mired in poverty, and this was only exacerbated by the Great Depression, which left millions of people in dire straits.
Bennett knew he had to get out...but he took a far from glamorous route.
6. He Got A Weighty Duty
In 1944, when he was just 18 years old, a drastic change came for Bennett. The US Army drafted him into WWII, even as the Allies were carrying out the final stages of the conflict. His training was a nightmare from the very beginning, with one of his commanding officers hating him so much, he often picked on the future crooner. Only, there's more.
7. He Was In A Living Nightmare
Even though it was the tail-end of the conflict, Bennett did not get off easy. In fact, he went to the frontlines. While there, he endured incredibly harsh winters and even liberated a camp near Dachau. Bennett would later call it "a front row seat in hell" and say his experiences were "a nightmare that's permanent".
When he finally escaped this nightmare, Bennett was more certain than ever he wanted to spread joy through music, not pain through violence. Well, he had someone to help him with that.
8. He Got A Lucky Step Up
Bennett’s truly big singing break came thanks to famous singer Pearl Bailey. In 1949, she noticed him—and his incredible voice—as he was struggling to get his foot in the door of the music industry. Knowing a hit-maker when she saw one, Bailey invited Bennett to open for her shows in Greenwich Village.
It turned out to be a date with destiny.
9. He Was In The Right Place At The Right Time
When Bennett opened that night for Bailey, he got the luckiest break of his life. In the audience that night was none other than the legendary comedian and entertainer Bop Hope, who was right on Pearl Bailey's wavelength. Wanting to capitalize on Bennett's obvious talent, he invited the young man to tour with him.
But first, Hope wanted Bennett to change something big.
10. He Got Advice From A Legend
Believe it or not, Bennett’s original stage name was actually “Joe Bari,” after the city and province in Italy. He used this name with the 314th Army Special Services Band and continued to use it after he left the military. But when Bob Hope took him under his wing, he convinced Bennett to just use a version of his real name, "Tony Bennett."
It didn't take long at all before a star was born.
11. He Turned Into A Heartthrob
By the 1950s, Bennett's career was well and truly off the ground, and his ballad "Because of You" became a hit at all the jukeboxes across America. Of course, Bennett's square-jawed good looks also helped his popularity, and soon he had scores of teenage girls attending his concerts.
Those teenage girls were not happy about the next development.
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12. He Fell In Love
Just as Bennett's popularity was taking off, he made a very controversial decision. Well, controversial for his fans at least. At the same time "Because of You" was climbing the charts, Bennett met the young, pretty Patricia Beech after one of his nightclub shows. The next year, he decided to marry her...and chaos broke loose.
13. His Fans Went Wild
As news of Bennett's upcoming nuptials got out, his fans' reaction was bizarre. As a kind of protest for the end of his bachelorhood, two thousand female fans gathered outside the church as he got married, dressed in black to denote their mourning. Yes, he was that popular.
But for Bennett, it was on to the next.
14. He Was On Top Of The World
1962 was an enormous year for Tony Bennett. Following up the success of even more hit singles like "Rags to Riches," Bennett released the massively popular "I Left My Heart in San Francisco" from his album of the same name, which nabbed him a Grammy. He'd finally made it, and his next life event proved it.
15. He Became A Superstar
In 1962, Bennett made a momentous first. He was a musical guest on the very first episode of The Tonight Show starring Johnny Carson. As many of your grandparents will tell you, The Tonight Show would make Johnny Carson a household name to an entire American generation, and Bennett had a piece of that pie.
Still, this is about when the cracks started to show.
16. His Relationship Crashed And Burned
Bennett's marriage to Patricia Beech was good for a while, but not forever. They had two sons together, D'Andrea (Danny) and Daegal (Dae), but these bundles of joy weren't enough to keep their problems at bay. In 1965, the couple announced their separation, and the reason was eyebrow-raising.
17. He Was A Workaholic
It wasn't that Bennett and Beech didn't love each other, it was that Bennett loved his work more. He was used to a rise and grind mentality, and was constantly on the road. None of his successes were good enough for him, and he made sure to constantly be working, working, working.
It wasn't a strong foundation for a good marriage—but there was a more scandalous issue.
18. He Had A Wandering Eye
Yes, Bennett and Beech broke up over his long days on tour, but that wasn't all. The divorce papers revealed a dark side to their relationship. According to Beech's filing when they finally made it official in 1969, the reason for the divorce was "adultery".
Apparently, Bennett wasn't always a faithful husband when he was far away from home. And well, Bennett did move on fast.
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19. He Rebounded Quick
Very shortly after he and Beech separated, Bennett began living with burgeoning actress Sandra Grant, whom he had met while making the film The Oscar the same year his marriage fell apart. Yes, the timing is more than suspicious, and Bennett's ensuing decisions weren't so rational.
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20. He Got Married Again
In the wake of a messy divorce, you might think it best to settle down for a bit and live a quiet life. Well, Bennett didn't think so. He and his formerly illicit lover Sandra Grant tied the knot in 1971, sending Bennett down the aisle for the second (but not last) time.
With Grant, he'd go on to have two more children, daughters Joanna and Antonia. But this new marriage was also the beginning of the worst period of his life.
21. He Made A Bad Career Move
The 1970s were a horrific decade for Bennett. Studios wanted crooners like him to stop singing the old standards, and instead try their hand at more rock-like music. The results were catastrophic. Bennett hated doing those kinds of songs, the studios hated his efforts, and audiences were indifferent. But that wasn't the worst of it.
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22. He Had One Crucial Flaw
Bennett had an incredible singing talent, but zero instinct for business maneuvers. Which made it a particularly bad idea when he started his own record company, Improv, in the mid-70s. He wanted to leave big studios behind, but soon found out that being a studio executive was a harder job than it appeared.
By 1977, the label had folded, and Bennett had almost nothing. He eventually resorted to desperate measures.
23. He Made A Tearjerking Call
In 1979, Bennett made a heartbreaking phone call. He rang up his sons Danny and Dae and told them, "Look, I'm lost here. It seems like people don't want to hear the music I make". Danny in particular—as an aspiring artist himself—wanted to help his father. He came up with a life-saving idea.
Danny had now been trying for quite some time to get his own band into the marquee lights, but had met with little success. However, it was partly this call that made Danny realize that while he wasn't a world-class artist like his father, he was better at business.
Then and there, Danny decided to become his father's manager. It was the best decision the Bennetts ever made.
25. His Career Turned Around
Over the next decade, Danny worked hard to get his father's career back on track. He tracked his expenses, set him up in New York instead of the cheesier Vegas venues he had been playing during his decline, and even got him back onto Columbia Records in 1986.
These years would produce even more chart-topping albums for Bennett and an Oscar nomination for Best Original Song. But then Danny had another stroke of brilliance.
26. He Made A Smart Choice
Unlike the stuffy executives that had pushed Bennett into rock music, Danny thought young audiences would respond to his father just the way he was. Accordingly, Danny began booking him for venues like Late Night with David Letterman and other "hip" shows. It produced an amazing effect.
Even though Bennett was still singing his old standards, these new audiences were rapt. As he put it, "I realized that young people had never heard those songs. Cole Porter, Gershwin—they were like, 'Who wrote that?' To them, it was different. If you're different, you stand out". This only grew as time went on.
The 1990s saw huge boost in Bennett’s popularity with younger audiences. This was partly due to his appearance on the widespread TV series MTV Unplugged. Accompanied by Elvis Costello and k.d. Lang, Bennett bridged the gap in generations who were used to rock music or hip-hop.
This led to his MTV Unplugged album going platinum. That wasn't the only way Bennett kept in touch with the younger generation.
29. He Was Always Looking For New Talent
In 2011, Bennett collaborated with America’s Got Talent runner-up Jackie Evancho to make a new duet version of the classic Disney tune “When You Wish Upon a Star". Did I mention that Evancho was 73 years younger than Bennett?
This was the new Bennett: Always interested in the future of music, and always willing to give young people their start, just like Pearl Bailey gave him his. But this renaissance didn't save Bennett from heartache.
30. His Marriage Fell Apart Again
Bennett's second wife Sandra Grant had stayed with him through some of the worst years of his life. But just as it began to turn around for him in the early 1980s, Grant and Bennett realized they had nothing left in the tank, and they divorced in 1983.
Only, as always with Bennett, he just couldn't give up. This wasn't the end for his love life.
31. He Finally Met His Soulmate
In the late 1980s, Bennett got a third chance at love with Susan Crow, a retired schoolteacher from New York. This time, Bennett made sure to take it very slow, and the pair only married in 2007, when Bennett was in his 80s. They remained married for the rest of his life.
32. He Refused To Retire
Even when he was in his 90s, Bennett refused to even consider retiring from the showbiz life or the art world. He once compared his situation to those of Jack Benny, Pablo Picasso, and Fred Astaire, stating that those men never retired either. Of course, it didn't quite work out that way for him.
33. He Was A Natural Talent
One of the signature traits of Bennett’s concerts was the moment where he sang a song without the help of any microphone or amplification. Bennett did this to prove the power of his own voice and his talent at voice projection. Usually, the song he sang during these demonstrations was “Fly Me to the Moon".
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34. He Got A Huge Present
One of Bennett’s most famous singles is still his recording of the classic song “I Left My Heart in San Francisco". On August 19, 2016, the Fairmont Hotel in San Francisco honored Bennett’s 90th birthday and the anniversary of his performing “I Left My Heart in San Francisco” by unveiling an 8-foot tall statue of Bennett.
35. He Had A Talented Daughter
One of Bennett’s four children is his daughter, Antonia. Throughout the 2000s, he very often brought her on as an opening act, or else as a guest voice. In 2002, critics compared Antonia’s singing to the likes of Billie Holiday and Jane Monheit. Her debut album, Embrace Me, came out in 2014.
36. He Had Big Shoes To Fill
Bennett spent his early life growing up to the music of Louis Armstrong, Bing Crosby, Al Jolson, Judy Garland, and Joe Venuti. You can’t get better inspirations than those if you want to get into jazz!
37. He Was A Good Friend
Bennett was a very good friend to fellow singer and music star Frank Sinatra. He showed his love in a wonderful way. In 2001, around three years after his friend’s passing, Bennett founded The Frank Sinatra School of Performing Arts in Sinatra’s honor. The school stands in Bennett’s home borough of Queens, New York City.
38. He Had A Hidden Talent
As a boy, Bennett showed a remarkable talent in school for drawing and visual arts. He was famous throughout his school as a caricaturist. At this point, Bennett assumed that he would go far in the world of art, and while he’d be correct, he wasn’t quite correct about what kind of art he’d be famous for.
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39. He Was A Drop-Out
Bennett enrolled at the School of Industrial Art in New York for singing and painting. Sadly, he never completed his studies, as he dropped out when he was 16 years old to financially assist his family. He never did forget his school’s lessons on proper technique, however...and it paid off big time.
40. He Had A Second Career
If you thought we were joking about Bennett’s talent for drawing, keep in mind that his artwork could sustain him even without his singing career. Various magazines printed his art, and his pieces regularly sold for prices up to $80,000. Not bad for a crooner.
41. His Talent Was No Joke
In case you assume that Tony Bennett was only an accomplished artist because of his singing career, know this: Super prestigious art institutions currently hold works by Bennett, including none other than the Smithsonian American Art Museum (yes, that Smithsonian American Art Museum).
42. He Was Also A Writer
Not only does Bennett’s artwork sell, but he also published two books about his lesser-known passion for art. Tony Bennett: What My Heart Has Seen came out in 1996 and featured much of his then-completed works, while Tony Bennett in the Studio: A Life of Art & Music came out in 2007 to great success.
43. He Kept His Careers Separate
Perhaps in an effort to separate his singing career from his career as an artist, Bennett painted under his real name, Antonio Benedetto. Even then, he sometimes shortened his name to simply “Benedetto” when he signed autographs or his paintings.
44. He Was An Actor, Too
Aside from his songs appearing in countless soundtracks in the world of film and television, Bennett himself also personally appeared in several films and TV shows, usually as himself. Some of his on-screen credits included Entourage, Bruce Almighty, 30 Rock, and Muppets Most Wanted.
Still, he didn't even appear at all for his most famous cameo.
45. He Got The Simpsons Treatment
In addition to appearing in the flesh in film or TV as himself, Bennett also provided his voice for an episode of The Simpsons. In the 19th episode of the 24th season known as “Whiskey Business,” Bennett appears as a singer in a jazz club, singing alongside a hologram of Bleeding Gums Murphy.
46. He Got Many Accolades
Over his life, Bennett won an astounding 20 Grammy Awards, including a Lifetime Achievement Award in 2001. He also received nominations for several other Grammy awards that he didn’t win. Besides the Grammy awards, Bennett also won two Emmy Awards for live performances on television.
47. He Was A Late Bloomer
For all Bennett’s success, there was one achievement that almost eluded him. He incredibly didn't get a number 1 album until 2011. Duets II, which came out on his 85th birthday, contained collaborations with the likes of Lady Gaga, Norah Jones, and Willie Nelson.
With Duets II, Bennett became “the oldest living musician to ever debut at No 1 on the Billboard 200".
48. He Made A Swan Song
Duets II has another claim to fame, but this one is tragic. The album also features a duet between Bennett and Amy Winehouse, singing “Body and Soul”. The two would share a Grammy award for Best Pop Duo. Sadly, this contribution to Duets II was also Winehouse’s last recording before her tragically premature passing.
49. You Can Still Visit Him
Anyone interested in finding Bennett’s star on the Hollywood Walk of Fame should go to 1560 Vine Street.
50. He Got A Scary Diagnosis
Bennett's work ethic was old school to the extreme, given that he continued performing well into his 90s. But he was hiding demons behind the stage. Doctors actually diagnosed Bennett with Alzheimer's all the way back in 2016, and he had to retire from performing in 2021. There were heartbreaking moments along the way.
51. He Was "Lost And Bewildered"
In 2021, when Lady Gaga and Bennett released their album Love for Sale, Bennett once more cemented his place in the hearts and minds of the younger generation. Yet the reality of the recording studio could be harsh. Reportedly, Bennett was sometimes "lost and bewildered" during his sessions.
Yet for all that, he continued fighting.
52. He Was A Pro Until The End
According to Bennett's son Danny, although the legendary crooner did have difficulty with his short-term memory—often not realizing he had just performed a concert to a huge crowd—his long-term memory was as perfect as ever, and the nonagenarian would sing his lyrics flawlessly.
But the end comes for everyone, even someone as monumental as Tony Bennett.
On July 21, 2023, Tony Bennet finally gave his last bow, passing at the age of 96 after suffering from Alzheimer's for the better part of a decade. But his final moments were incredible. A crooner to his bones, his family revealed he kept singing to the very end, going out with the song "Because of You"—his very first hit.
Still, Bennett kept some of the darker sides of his life away from the public eye.
54. He Dealt With Addiction
In the worst times of his life, during the 1970s, few people know just what Bennett was struggling with. In addition to declining album sales and popularity, Bennett had also gotten very into the party scene, showing a particular penchant for the white stuff.
As he later put it, "At first, it seemed like the hip thing to do, but as time went on it got harder and harder to refuse it". This soon turned into the most dangerous moment of his life.
55. His Low Point Was Unbelievable
In 1979, Bennett reached a terrifying rock bottom. He suffered through a horrific overdose that left him reeling, especially in combination with his failing career and marriage. In fact, that desperate call he made to his son Danny, the one that turned his life around, occurred just after this moment.