Tony Bennett Through the Years: Grammy Wins, Family Life, Retirement and More

From rags to riches! Tony Bennett has had a long and successful career as a jazz artist – but the “Because of You” singer started out with humble beginnings.

The 19-time Grammy award winner (real name Anthony Dominick Benedetto) was born in Queens, New York in 1926 to a low-income family. His father, Giovanni “John” Benedetto, was a grocer and his mother, Anna Maria Suraci, was a seamstress. The Great Depression hit the family hard as John’s health declined. He died by the time Bennett was 10 years old.

The New York native began singing from a young age and would practice while waiting tables in order to help his family financially. “I started when I was about 6. I never met an Italian descent family in America that isn’t musical,” Bennett said in an interview with Jazz Professional in 1966.

The “I Left My Heart in San Francisco” artist had his big break in 1949 when vaudeville singer Pearl Bailey invited him to open for her concert series in Greenwich Village. Entertainer Bob Hope attended one of the performances and offered Bennett a spot in his show at the Paramount Theater. At the time, Bennett was going by the stage name Joe Bari and it was Hope that suggested he change it to Tony Bennett.

One year later, the crooner signed with Columbia Records and released chart-topping songs including “Because of You” and “Blue Velvet.”. He won his first Grammy in 1962 for his recording of “I Left My Heart in San Francisco” and would continue to collect a total of 19 wins with 41 nominations.

Bennett stayed in the spotlight throughout the decades by gaining popularity with a younger audience, even as pop music began to shift and change in the ‘90s. His 1994 appearance on MTV Unplugged resulted in a platinum album and a Grammy win for Album of the Year.

Bennett continued to achieve great success and recognition throughout the 2000s, including being honored with the Grammy Lifetime Achievement Award in 2001 and receiving the Kennedy Center Honors Award four years later. It was in 2011 that he began a close-knit friendship with Lady Gaga, who would become a frequent collaborator over the next decade.

Bennett and the “Just Dance” artist released the Grammy-winning album Cheek to Cheek in 2014, while also earning Bennett – who was 88 at the time – a Guinness World Record for “oldest person to reach No. 1 on the U.S. Album Chart with a newly recorded album.” The duo also released a concert special, Tony Bennett and Lady Gaga: Cheek to Cheek Live!, in celebration of the record’s popularity. Bennett’s final album was released September 2021, and it was another collaborative effort with Gaga, this one entitled Love For Sale.

One month prior, Bennett announced his retirement amid his Alzheimer’s diagnosis. His final live and recorded performances with the “Shallow” artist were turned into the TV special, One Last Time: An Evening with Tony Bennett and Lady Gaga, which debuted in November that year.

Throughout the “Love For Sale” singer’s enormous career success, he’s also found love numerous times. Bennett married his first wife, Patricia Beech, in 1952 and together welcomed two sons, Danny and Dae, before finalizing their divorce in 1971. Bennett welcomed his first daughter, Joanna, in 1970, with his second wife, Sandra Grant, whom he wed after his divorce from Beech. The couple went on to have another daughter, Antonia. The duo separated in 2007, and Bennett married his third wife, Susan Crow, that same year.

Keep scrolling to see Bennett’s life and career in photos: