Tony Bennett was a true American legend, with one of the richest voices ever committed to vinyl.
From his humble beginnings to his low points with addiction, this is the story of how he
hit the big time in the early 1950s, and stayed there for the rest of his life.
If you want to get good at something, you've got to do that thing a lot.
By the time he was ten years old in 1936, Anthony Benedetto was already singing for
crowds, including at the opening of the Triborough Bridge in New York City.
At the age of 16, he dropped out of school to earn money for his family, and he naturally
pursued what he was good at: singing.
Benedetto landed a job as a singing waiter in a Queens, New York, restaurant.
Interrupted briefly by a stint in the military during World War II, Benedetto returned to
the States and performed at any place that would have him.
One day in 1949, the legendary Broadway performer Pearl Bailey heard Bennett sing at an audition,
and asked him to be her opening act for a run of shows in Greenwich Village.
Bob Hope, arguably the most famous and popular entertainer of the day happened to be in the
house one night and asked him to come perform in his show, too.
But Hope wanted the crooner to drop the "Joe Bari" moniker.
Hope asked Benedetto to tell him his real name, and quipped that it was "too long for
the marquee."
So, he shortened the singer's real name, Anthony Benedetto, to Tony Bennett, and a star was born.
In November 1944, 18-year-old Tony Bennett got his draft papers and was shipped out for
army training at Fort Robinson in Arkansas.
Almost immediately, Bennett realized that military life was not for him.
He wrote in his autobiography, "The Good Life,"
"They treated us like animals.
I began to have a really hard time with the whole military philosophy.
From top to bottom, it went against every single thing I believed in."
Even worse than the training that was designed to, "brutalize us and break our spirit," Bennett
had to deal with some pernicious racism.
He wrote,
"Our sergeant was an old-fashioned southern bigot, and he had it in for me right from
the start because I was an Italian from New York City."
He also revealed that it was "just as bad for other ethnic groups," particularly African-American
and Jewish soldiers.
Bennett found himself stationed in Germany during the waning days of the war.
Along with the rest of the 255th Regiment, Bennett captured several Nazi SS soldiers.
In their last mission, they were tasked with liberating a concentration camp.
Bennett said,
"I'll never forget the desperate faces and empty stares of the prisoners.
They had been brutalized for so long that at first, they couldn't believe that we were
there to help them and not to kill them."
His wartime experiences left Bennett a pacifist for life.
"I really dislike war.
See, to me, life is a gift, and you should enjoy it.
As an Italian-American entertainer living in New York City in the 1940s, it wasn't hard
for Bennett to run into the mob, or to employ their services.
According to David Evanier's "All the Things You Are: The Life of Tony Bennett," by 1949,
Bennett was tired of getting nowhere under his old manager, so he hired a new one.
Ray Muscarella was a promoter with purported ties to organized crime families.
He used his money and connections to get Bennett in touch with a vocal coach, arrangers, composers,
a publicist, and a record promoter.
Muscarella also funded the whole operation, meaning Bennett ultimately owed the mob and
he owed them big.
According to sources in "All the Things You Are," the money that launched Bennett's career
came from the Capone family.
The singer dutifully performed at mafia-sponsored gigs for years, and it wasn't until the late
'60s Bennett set himself free, paying $600,000 to organized criminals so as to be left alone.
Tony Bennett signed with Columbia Records in the early 1950s, but he was a bit skeptical
of his record deal.
He signed with Columbia right when its biggest star, and Bennett's idol, Frank Sinatra, was
leaving the label.
But his worries ended up being unfounded.
Columbia allowed him to sing in his own style, and it definitely helped him get noticed.
Bennet was praised for his voice, even by Frank Sinatra who said of the singer,
"For my money, Tony Bennett is the best singer I've ever heard."
Bennett considered Sinatra a mentor.
Even after he'd scored two #1 hits in "Because of You" and "Cold, Cold Heart," Bennett still
had some stage fright.
In an interview he gave on "The Tonight Show," Bennett revealed that Sinatra gave him some
very good advice.
"He taught me, that the audience are your friends, they come to see you."
Bennett continued by saying,
"And he changed my whole psychology about that, there's no such thing as a bad audience.
There's a bad performance, but there's not a bad audience."
Bennett even lived in Ol' Blue Eyes' stomping ground of Las Vegas for nearly 20 years, and
yet he politely refused to join the Rat Pack, Sinatra's semi-official bad-boy friend group.
Bennett didn't think he was as tough as the likes of Dean Martin and Peter Lawford, and
besides, as he told The Independent, "They kept awfully long hours."
In the late 1950s, songwriters George Cory Jr. and Douglass Cross ran into Bennett's
pianist, Ralph Sharon, in New York, and gave him the sheet music for several new songs,
including "I Left My Heart in San Francisco."
Sharon didn't think much about them and tossed the papers into his shirt drawer where they
sat for nearly two years.
While packing for a tour with Bennett in 1961, he came across that sheet music and rediscovered
"I Left My Heart in San Francisco."
After a show in Arkansas one evening, Sharon played the song at a piano in a hotel bar,
and Bennett loved it.
Not too long after, the tour took Bennett and Sharon to San Francisco, where they performed
what became Bennett's signature song for the first time at the Venetian Room in the Fairmont
Hotel just before Christmas.
Initially, Columbia Records placed Bennett's recording as the B-side of the single "Once
Upon a Time."
But DJs around the country discovered the vastly superior song and played it over the
A-side track.
It also helped that Bennett sang the song during Johnny Carson's first night as host
of "The Tonight Show."
These days, artists aren't shy about utilizing their voices and visibility to advance a cause,
but in the '60s, it wasn't done that way.
Only a handful of famous people were willing to risk alienating their fanbase to stand
up for what was right, and Tony Bennett was among them.
In the 1960s, Bennett advocated for the Civil Rights Movement, participating in the Selma
March of 1965 organized by Dr. Martin Luther King Jr.
While he was a worldwide star, Bennett refused to perform concerts in South Africa due to
the country's separatist apartheid laws.
His reasons for doing so were wonderfully simple.
He told PBS,
"We are all human and we are all on this planet together.
So what better reason do you need to not tolerate any form of violence against another human being?"
Bennett did so much work in the name of justice that he was honored by the International Civil
Rights Walk of Fame and was awarded the Martin Luther King Center's Salute to Greatness Award.
For most of Tony Bennett's career, he stood firm in his preferred genre of music.
He crooned jazz standards and entries in the great American songbook for more than 60 years.
He didn't care much for rock n' roll and its offshoots, and he once said that the Rolling
Stones promoted "juvenile delinquency."
But Bennett did try to keep up with the hip young kids once, and it didn't go well.
In 1967, he covered Stevie Wonder's smooth and jazzy "For Once in My Life" at the behest
of Columbia Records' new president, Clive Davis, who wanted to bring old crooners like
Bennett into the new age.
Bennett reluctantly recorded an album in 1970 called "Tony Sings the Great Hits of Today!"
The album cover featured Bennett rocking some groovy threads, and the record inside featured
Bennett's take on Wonder's "My Cherie Amour" and The Beatles' "Something" and "Eleanor Rigby."
The album didn't sell well, and neither did a hastily released follow-up "Tony Bennett's Something."
Then, In 1972, Columbia dropped Bennett after two decades with the label.
Tony Bennett doesn't seem like the kind of performer who would fall into the traps of
the rock n' roll lifestyle, but Bennett fell into drug abuse and nearly destroyed his life
during the 1970s.
He admitted in his book, "All the Things You Are: The Life of Tony Bennett" that he "used
to take pills — uppies, downies, and sleepies."
He identified the '70s as his "darkest period."
After Columbia Records dropped him from its roster in the face of changing musical tastes,
he fell deeply into debt.
He said,
"I owed something like $1.2 million, which was a fortune in those days.
At least half of it was in back taxes I couldn't afford to pay."
The death of his mother on Thanksgiving 1977 was unbelievably painful, and he, quote, "turned
more and more recklessly to drugs for relief."
Things got even worse in 1979.
That's when Bennett, freaked out over a call to his accountants from the IRS threatening
to seize his house, overdosed on cocaine, and passed out while in his bath.
His then-wife Sandy Grant arrived home just in time to get him to a hospital.
Bennett eventually got clean and sober and his son, Danny, helped him settle his financial problems.
Tony Bennett was the last man standing from the pre-rock era, by virtue of surviving and
performing into his 90s as well as a slow and savvy marketing plan.
Danny Bennett took over his father's career in 1979 and got his father a new deal with
his old label, Columbia Records.
In 1986, "The Art of Excellence," the first album under that contract, became Bennett's
first record in 14 years to hit the charts.
Around that time, Spin publisher Bob Guccione Jr., called Bennett one of the two biggest
influences on rock n' roll and published a featured profile of the crooner.
Before long, Bennett was regularly appearing on "Late Night with David Letterman" and booking
spots in alternative rock radio station-sponsored concerts – such as at Radio City Music Hall.
"Yeah, they've commissioned me to sing all the great songs that were introduced right
at Radio City."
All the while, Bennett didn't change a thing about his act.
He sang great songs and the rock fans loved him for it.
Columbia Records played up the nostalgia factor, and released two Bennett concept albums in
1992 and 1993: the Frank Sinatra tribute "Perfectly Frank" and the Fred Astaire tribute "Steppin' Out."
Those won Bennett back-to-back Grammy Awards for Best Traditional Pop Vocal Performance.
A video for the title track from "Steppin' Out" received heavy MTV airplay in late 1993,
prompting the network to book Bennett for an episode of its "Unplugged'' concert series.
In 1994, the live recording of Bennett's "Unplugged" won the Grammy Award for Album of the Year.
A survey of Tony Bennett's romantic history is almost as long and involved as his discography.
In 1952, he married Patricia Beach, the mother of his two sons, one of whom, Danny, is his manager.
She filed for divorce in 1969, after Bennett allegedly cheated with actress Sandra Grant,
whom the singer married and helped raise two daughters.
That relationship lasted until 1979, and Bennett wouldn't marry for a third time until 2007,
saying I do to Susan Crow, a woman 40 years younger than the singer.
According to Bennett's book "Just Getting Started," they first met decades earlier.
At 19, Crow was the president of Bennett's Bay Area fan club and requested to say hello
backstage after one of his shows.
Bennett wrote that he was touched "that someone of her age was so devoted to my music."
Crow got that backstage pass, and a little bit more, as Bennett asked her out on a date.
But this is where it gets weird.
Crow's parents were big Bennett fans, too.
In 1966, they caught one of his concerts in San Francisco.
Bennett posed for a picture with the Crows, and Marion Crow happened to be pregnant at
the time, with Susan.
Tony Bennett's struggles with drug addiction left him near death in the 1970s, and he worked
hard to get sober.
But his experiences with drugs didn't leave him hardened as to their wider use in society.
In 2012, Bennett was at a pre-Grammy party when news of Whitney Houston's death from
drowning, with drugs being a complicating factor.
Coming soon after the deaths of Michael Jackson and Amy Winehouse, Houston's death moved Bennett
to speak.
During the party he spoke to the guests, saying,
"I'd like to have every gentleman and lady in this room commit themselves to get our
government to legalize drugs."
He noted that such a policy would at least put access to dangerous drugs in the hands
of doctors rather than drug dealers.
Bennett faced some criticism for his remarks, but also support from several police officers
and rehab professionals who agreed with his opinions about the legality of drugs.
As Tony Bennett, he was a world-renowned singer.
Under his birth name, Anthony Benedetto, he maintained a side career as a painter.
Bennett had been fascinated by art and painting since childhood, and according to PBS's "American
Masters," he made it a daily practice.
It's a habit he maintained even while touring.
"Well I'm still painting, and I still love it very, very much."
His paintings were the subject of his first book, "What My Heart Has Seen," published
in 1996.
Bennett's art has appeared in several museum galleries.
A painting of David Hockney is part of the Butler Institute of American Art's permanent
collection, and he has pieces in the National Arts Club and the Smithsonian's American Art Museum.
He's been commissioned by the Kentucky Derby for promotional material and the United Nations
for an anniversary painting.
And Bennett's art has been a regular part of the American Cancer Society's holiday fundraising;
he painted many of their greeting cards.
Tony Bennett kept busy throughout the 2010s, carrying out touring concerts and striking
up a friendship and collaboration with Lady Gaga.
However, in 2017, Bennett was diagnosed with Alzheimer's disease.
The bad news was initially kept private, and Bennett insisted on keeping up with his performances.
But by 2021, though his voice and musical recall were still strong, his physical condition
at 95 couldn't endure his performing schedule anymore.
That year, Bennett made public that he had Alzheimer's, and his son Danny announced that
there would be no more concerts.
Danny told Variety:
"This was a hard decision for us to make, as he is a capable performer.
This is, however, doctor's orders."
Danny added that his father would be doing "other things," though he didn't elaborate
on what those might be.
The family didn't issue permission for a post-retirement use of Bennett's image in an episode of "The
Marvelous Mrs. Maisel," though there were no hurt feelings.
A year after retirement, Danny shared that his father still rehearsed three times a week.
Danny told Variety:
"That's how you do it.
It's like "How do you get to Carnegie Hall, right?
Practice.'"