Tony Bennett Makes Grammy History as Second Oldest Winner

Videos by American Songwriter

Videos by American Songwriter

At 95. the jazz maestro, standards great, visual artist, singer, and songwriter Tony Bennett has made Grammy history as the second-oldest artist to win the award.

Bennett picked up his 20th Grammy Award along with Lady Gaga for Best Traditional Pop Vocal Album for the duo’s 2021 release Love for Sale, a collection of Cole Porter standards during the April 3 ceremony.

The New York crooner falls just behind Pinetop Perkins, who is the oldest winner of a Grammy to date. The 97-year-old pianist took home a Traditional Blues Album Grammy in 2011 for his album Joined at the Hip, just a month before he died on March 21.

Bennett’s latest Grammy win comes nearly 60 years after he first wins at the fifth Grammy Awards in 1963 when he picked up Record of the Year and Solo Vocal Performance for “I Left My Heart In San Francisco.” Of Bennett’s 20 Grammy awards to date, 14 of them are now from the Traditional Pop Vocal Album category. In 2021, Bennett was also given the Lifetime Achievement Award at the Grammys for his contribution to music. This also marks the 13th Grammy win for Gaga.

In addition to their Traditional Pop Vocal Album win, Gaga and Bennett were nominated for six Grammys in total, including Album of the Year, Best Engineered Album, Non-Classical, Record of the Year for the single “I Get a Kick Out of You,” and Best Pop Duo/Group Performance and Best Music Video. The pair won the Grammy for Traditional Pop Vocal Album for their first album collaboration Cheek to Cheek.

In 2021, Bennett revealed that he was diagnosed with Alzheimer’s in 2016 and gave his last live performance at Radio City Music Hall on Aug. 3. His final two performances were recorded for the concert special One Last Time: An Evening With Tony Bennett & Lady Gaga. The making of their album Love for Sale was also captured in a documentary The Lady and the Legend, which is set to release on Paramount+ in 2022. 

“I’m so honored to be his companion in music and his friend,” wrote Gaga on Instagram after the Grammy nominations were announced in November 2021. “Thank you to the public for loving us, we surely love each other, and you. Believe in love and partnership, even with 60 years between us, and Alzheimer’s, there is nothing like the magic of music. I love you Tony, and the world loves you too. How could they not?”

Lady Gaga performing Cole Porter classics at the 64th Annual Grammy Awards (Photo: Cliff Lipson/CBS)

Accepting Bennett’s Grammy was his son Dae along with Gaga. Though Bennett was invited to perform with Gaga, his condition prevented him from attending and performing at the ceremony. “Although the producers had invited both Tony and Gaga to perform in Sunday’s Grammys broadcast, it is unfortunate that due to his continuing struggle with Alzheimer’s, he was not able to accept,” said Bennett’s son Danny, who has also served as his father’s manager for 40 years, in a statement prior to the Grammys. “It was decided that it would be fitting for Lady Gaga to perform on her own to represent for both of them.”

He added, “There is no doubt, that she will offer up an impeccable performance from ‘Love for Sale,’ which is Tony’s final album. He will be cheering her on as he watches from his home in New York City.”

Bennett still made a brief appearance on a video feed to introduce Gaga, who performed an emotional medley of the duo’s Porter standards “Love for Sale” and “Do I Love You,” with a video screen background showing footage of the duo recording the album in the studio.

Gaga ended her Grammy performance with a message to Bennett.

“I love you, Tony,” she said. “I miss you.” 

Photo: Mark Seliger

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