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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. One of the most iconic Italian American musicians this side of Frank Sinatra, Bennett’s career has seen incredibly longevity and diversity, even compared to his peers. If you’ve ever been curious about that guy singing a song in the background of half the Mafia-related movies or TV shows that you’ve ever seen, give this article a chance and read all about Tony Bennett!


1. How About a Tip Mr. Mayor?

By age 10, Bennett was already gaining attention with his singing. Thanks to his uncle’s position as a Queens Borough library commissioner, the young Bennett was brought 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 City’s then-mayor Fiorello La Guardia and received a pat on the head from the mayor in appreciation of his voice.

2. Welcome to the World

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.

3. What’s in a Name?

Bennett’s original stage name was actually “Joe Bari,” named after the city and province in Italy. He initially used this name with the 314th Army Special Services Band and continued to use it after he left the military. However, he switched to “Tony Bennett” in the late 1940s, on the advice of Bob Hope.

4. Sketching His Way to Success

As a boy, Bennett showed a remarkable talent in school for drawing and visual arts. He was known throughout his school as being 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 best known for.

5. You Don’t Mean it!

Tony Bennett first started singing for money when he was 13 years old. His stages were the various Italian restaurants in his home neighborhood, as he was also working as a waiter during that time. We’re not sure what you guys will find less believable: that 13-year-olds would be working as waiters, or that those dining would want their waiters to sing!

6. Lessons for the Road

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.

7. Farewell, Father

Bennett’s father, John, was responsible for instilling a passion for art and literature in his son. Sadly, John was frequently ill and died when Bennett was just 10 years old.

8. Steeped in Squalor

The illness and premature death of Bennett’s father meant that the family grew up in poverty. Things were only exacerbated by the Great Depression, which left millions of people in dire straits.

9. Time to Serve

In 1944, Bennett was drafted into the US Army, even as the Allies were carrying out the final stages of the Second World War. The high casualty rate from such engagements as the Battle of the Bulge led to Bennett being assigned to the 63rd Infantry Division.

10. Heck of a Collection!

As of May 2019, Bennett has released 57 studio albums, 11 live albums, and 31 compilation albums! Of those albums, four of them went platinum while many others were certified gold by the RIAA.

11. I’ve Still Got It!

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.”

12. That Shining Pearl!

Bennett’s big singing break came thanks to Pearl Bailey. In 1949, she noticed him as he was struggling to get his foot in the door of the music industry. Bailey invited Bennett to open for her shows in Greenwich Village. The rest was history.

13. My Heroes

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!

14. The Start of Something Famous

In 1962, Bennett 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.

15. Wasn’t He Always Unplugged?

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!

16. Double the Fun

From 1992 to 1993, Tony Bennett released two albums which were tributes to two musicians and actors whom Bennett deeply respected. Perfectly Frank was a tribute to Frank Sinatra, while Steppin’ Out was a tribute to Fred Astaire. Both albums were certified gold by the RIAA and both won the Grammy Award for Best Traditional Pop Vocal Performance.

17. Hi Tony!

Anyone interested in finding Bennett’s star on the Hollywood Walk of Fame should go to 1560 Vine Street.

18. Like Father Like Daughter

One of Bennett’s four children is his daughter, Antonia. Throughout the 2000s, she was very often brought on as an opening act to her famous father, or else as a guest voice. In 2002, Antonia’s singing was compared to the likes of Billie Holliday and Jane Monheit. Her debut album, Embrace Me, was released in 2014.

19. Accolades Galore!

As of May 2019, Bennett has won 20 Grammy Awards, including a Lifetime Achievement Award in 2001. He’s also been nominated for seven other Grammy awards that he didn’t win. Besides the Grammy awards, Bennett has also won two Emmy Awards for live performances on television.

20. That’s a Profitable Hobby!

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 have printed his art, and his pieces regularly sell for prices up to $80,000!

21. No Joke!

In case you read the above point and simply assumed that Tony Bennett is only an accomplished artist because of his singing career, keep in mind that established and highly prestigious art institutions currently hold works by Bennett as part of their permanent collections. New York’s National Arts Club owns a work by Bennett titled “Boy on Sailboat, Sydney Bay.”

Meanwhile, you can go see Bennett’s “Central Park” at the Smithsonian American Art Museum (yes, that Smithsonian American Art Museum).

22. Young and Old Together

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.” Interestingly, there was over 73 years’ difference between the two singers!

23. A Hit in the Art Community

Not only does Bennett’s artwork sell, but two best-selling books have also been published about this lesser-known passion of Bennett’s. Tony Bennett: What My Heart Has Seen was published in 1996 and featured much of his then-completed works, while Tony Bennett in the Studio: A Life of Art & Music was published to great success in 2007.

24. Love at First Sound

After he performed a concert at a Cleveland club in 1951, Bennett met Patricia Beech, a jazz fan from Ohio. They were married on February 12, 1952, in Manhattan’s St. Patrick’s Cathedral.

25. Oh, Girls, You’re So Incorrigible!

Such was Bennett’s fame even then in the early 1950s, that when he got married to Patricia Beech, thousands of his female fans stood outside St. Patrick’s Cathedral. As a joke, the women all allegedly wore black, mourning the fact that their music idol was getting married.

26. Not in Hoboken?

Bennett was a very good friend to fellow singer and music star Frank Sinatra. In 2001, around three years after his friend’s death, 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.

27. So Which is the Pseudonym?

Perhaps in an effort to separate his singing career from his career as an artist, Bennett’s painting name is done under his real name, Antonio Benedetto. Even that, however, is sometimes shortened to simply “Benedetto” when Bennett autographs or signs his paintings.

28. Late Bloomer

For all Bennett’s success, he didn’t achieve a No. 1 album until 2011. Duets II, released on his 85th birthday, was filled with collaborations with the likes of k.d. Lang, 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.”

29. Swan Song

Speaking of Duets II, 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 death.

30. Joining the Cause

In 2010, a devastating earthquake ripped through the island nation of Haiti. As part of his humanitarian response to the tragedy, Tony Bennett was one of 70 different artists who sang on a charity single titled “We Are the World 25 for Haiti.”

31. Why, Thank You!

One of Bennett’s most well-known singles is his recording of the classic song “I Left My Heart in San Francisco.” Despite the fact that Bennett was from New York City, his song took the world by storm. 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 a statue of Bennett.

The statue is eight feet tall and the unveiling was witnessed by Senator Dianne Feinstein and House Minority Leader Nancy Pelosi.

32. Let the Good Times Roll!

Worldwide, Bennett has sold upwards of 50 million records over the course of his career!

33. Try and Beat That!

Bennett holds a rather interesting spot with the Guinness World Records. The record in question is “the longest time between the release of an original recording and a re-recording of the same single by the same artist.” Bennett’s song “Fascinating Rhythm” was re-recorded by Bennett nearly 69 years after he first released the song! We’re quite sure that kind of longevity won’t be matched for a long time (no pun intended).

34. And Featuring…

Aside from his songs being used in countless soundtracks in the world of film and television, Bennett himself has also personally appeared in several films and TV shows, usually as himself. Some of his on-screen credits include Entourage, Bruce Almighty, 30 Rock, and Muppets Most Wanted.

35. Who’s That on Stage?

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 visited by Lisa Simpson, singing alongside a hologram of Bleeding Gums Murphy.

36. Ahead of His Time

Following the Second World War, Bennett spent time in Germany as part of the occupying force. Bennett was initially assigned to a band which would entertain fellow troops. However, he was demoted and sent instead to the Graves Registration Service duties as punishment. What was his crime, you might ask? He was publicly dining with an old high school friend, who was black.

37. Staying Woke

If the US Military thought that punishing Bennett would stop him from breaking the racial segregation rules within the army, they were very wrong. Bennett became a passionate supporter of the Civil Rights Movement during the 1960s, he named Martin Luther King Jr. as a personal friend, and he participated in the marches from Selma to Montgomery. Years later, Bennett refused to perform concerts in South Africa for as long as the racist institution of apartheid was upheld.

38. Friends in the UN

In celebration of his life’s achievements, as well as coinciding with his 80th birthday in 2006, Bennett was awarded the Humanitarian Award by the United Nations High Commissioner for Refugees. He was also commissioned to make a painting in honor of the United Nations’ 50th anniversary.Fyodor Dostoevsky facts

39. The Older, the Busier

Even in his early 90s, Bennett refuses 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. Frankly, we can’t argue with that kind of logic!

40. Never Again

During his time with the 63rd Infantry Division, Bennett was on the front lines, participating in the invasion of Germany. The fighting was brutal, and Bennett nearly lost his life on multiple occasions. Even after the worst of the combat was done, Bennett participated in the liberation of the Nazi concentration camp in Landsberg.

Bennett would later describe his experiences as a “front-row seat in hell,” and became a lifelong pacifist in response to the brutality of the war.

41. Rock Bottom

In 1979, Bennett’s life was at a low point. His second marriage had fallen apart, and his records weren’t selling as they had during the 1960s and the mid-1970s. His attempt to form his own record company had led to bankruptcy, and Bennett himself was struggling with drug addiction. This came to a terrifying head when Bennett nearly died of a cocaine overdose that year.

42. Getting Back on Your Feet

The silver lining to Bennett’s near-death experience in 1979 was that he came to a new agreement with his grown son, Danny. Danny had tried to follow in his father’s footsteps as a musician, but it hadn’t worked out. However, unlike Bennett, Danny had a very good head for business, so it was agreed that Danny would become his father’s manager.

This proved to be the best decision ever made for Bennett’s career. Danny proved an effective manager, guiding his father into a major career comeback during the 1980s and 1990s.

Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10

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