The phrase "the end of an era" is often used without much thought in current times, but it truly applies to the passing of Tony Bennett.  Bennett was the last of the great crooners in the tradition of greats such as Frank Sinatra and Dean Martin.

He sold more than 50 million records across the world.  He won 20 Grammys and two Emmys and was a Kennedy Center Honoree.  In 2014, he broke his own record by becoming the oldest living recording artist at the top of the weekly Billboard 200 album chart.

But beyond the records he made and set, it was his ability to connect with newer generations that made him ageless and caused his career to span over seven decades.

Bennett's talents were best summarized by Frank Sinatra, who called him the best singer in the business.  Sinatra opined that Bennett was the rare singer who could convey through expressive voice exactly what the composer and lyricist had envisioned while being both exciting and moving.

Among Bennett's most loved hits were "Rags to Riches" and "I Left My Heart in San Francisco."

Bennett's beginnings were light-years from the wealth and fame he eventually achieved.  He was born Anthony Dominick Benedetto in August 1926 to Italian immigrants and grew up impoverished in Queens, New York.

His father, who struggled with ill health, barely managed to earn a living and eventually passed away when Bennett was just 10.  He was raised by his seamstress mother along with his two siblings. 

Both of Bennett's parents were musically inclined and supportive of their children's talents.  Bennett grew up listening to legends such as Bing Crosby, Louis Armstrong, and James "Jimmy" Durante on the radio.

Later in life, Bennett said that his father's early demise and the hard times that followed drove him to strive for success because it was a matter of survival for him.

In 1949, Bob Hope noticed his talent as a singer when he saw him perform at a Greenwich Village nightclub.  Hope gave him his stage name "Tony Bennett" and invited Bennett to tour with him across the U.S.

Bennett rose to prominence in a short time and had his first hit record, called "Because of You," in 1952, which remained on top of the U.S. charts for 10 weeks.

His cover of the Hank Williams country classic "Cold, Cold Heart" was also a huge success, as was "Rags to Riches."

The rock 'n' roll revolution led by Elvis had little impact on Bennett's popularity, and he thrived during the '50s with chart-toppers in the U.S. and across the world.  He also had a Broadway show tune, "Stranger in Paradise."

Like all great artists, Bennett seamlessly evolved with the changing times.  He gradually abandoned the ballads of the 1950s that had made him famous and began leaning towards jazz and singing with orchestral arrangements like Frank Sinatra.

In 1962, he released "I Left My Heart in San Francisco."  This wasn't an instant hit — yet it grew on listeners owing to its nostalgic essence about life on the west coast of America and eventually became his most popular song.

Not every reinvention of Bennett's was met with success.

When his popularity began to wane by the 1970s, Bennett recorded an album of contemporary pop covers titled Tony Sings the Great Hits of Today.  Bennett conceded that the effort was so awful that it caused him to vomit.

The '70s and '80s were also plagued by struggles.  He did perform occasionally in Vegas but seldom elsewhere.  As the decade neared its end, Bennett had no recording contract, no manager, and few singing engagements.

The only success Bennett had during the '80s was Henry Mancini's theme song "Life in a Looking Glass" from the motion picture That's Life (1986).  The song received a nomination at the Oscars for Best Original Song.

Bennett realized that his career needed a shock to be revived.  He turned to his sons Danny and Dae for help.  Danny understood that his father was a brilliant musical talent and that it was just a matter of presenting him in a different light that would make him appealing to a new generation.

The reinvention began with Bennett making appearances on the late-night shows of Jay Leno, David Letterman, and Conan O'Brien during the early '90s.

Bennett also appeared on MTV, whose key demographic was teenagers and people in their early 20s.  Then, in 1994, Bennett recorded his MTV Unplugged, where he performed many of his chart-toppers.  The "retro" settings were ideal for Bennett's kind of music; consequently, it was a huge success and caused his popularity to soar.

It led him to appear on The Simpsons and even Muppets Tonight, which added to his popularity.

In 1997, Bennett was given a star on the Hollywood Walk of Fame and was inducted into the Big Band and Jazz Hall of Fame.

To celebrate becoming an octogenarian in 2006, Bennett released an album featuring duets with legends such as George Michael, Paul McCartney, and Elton John.  The album was a huge success.

In 2011, he collaborated with Amy Winehouse just before her untimely death on a track called "Body and Soul."  The album made the Billboard Hot 100, making Bennett the oldest living artist to chart in its history.

He had further success the same year when he worked with Lady Gaga on a lively new rendition of "The Lady Is a Tramp" that injected new verve into the renowned song.

Gaga and Bennett recorded their first joint album in 2014, Cheek to Cheek, which debuted at No. 1 on the Billboard charts and sold three quarters of a million units in the United States.  It also led to a successful tour.

In 2021, their second album, Love for Sale, a tribute to the legendary Cole Porter, was a massive commercial success.

Also in 2021, it was announced that Bennett had been diagnosed with Alzheimer's, which caused him to give up performing live.

It is essential to state that Bennett's reinventions never involved any kind of compromise concerning his style.  He sang in the manner in which he had always sung, always respecting the lyrics and the composition.  He was always smiling and immaculately dressed in a suit and tie.  It is just that he chose contemporary settings and artists.

The contemporary artists worked with Bennett because it gave them an opportunity to perform the old-fashioned way, where the vocals and words mattered.  Bennett benefited from the popularity of these artists, who introduced him to new audiences.

Bennett's other passion was painting.  He did portraits of his musician friends and Central Park landscapes that were displayed in the Smithsonian Museum of American Art.

Bennett's voice has touched and enthralled millions of his listeners and transported them to another place.  The impression he has left is indelible. 

Bennett is also an inspiring figure for his indefatigable spirit and his ability to rise like a phoenix at junctures in his career when it appeared that all was lost.

Bennett had a good life, and it is essential not just to mourn Bennett's passing, but to celebrate his life and career.

Photo credit: Sarah Ackerman, CC BY 2.0 license.