5 of Tony Bennett’s Most Powerful Performances from His Hometown of New York City

A consummate showman, Tony Bennett knew how to hold a song, and an audience, in the palm of his hand, whether crooning “Cheek to Cheek,” or reminiscing of the morning fog and golden sun on “I Left My Heart in San Francisco” and the more buoyant “Fly Me to the Moon.”

Throughout his 70-plus career, Bennett left behind innumerable performances and duets with everyone from Frank Sinatra, Judy Garland, Billie Holiday, Barbra Streisand, Elton John, Stevie Wonder, and Amy Winehouse, among many others.

Here’s a look at five unforgettable live performances by Bennett over his storied career, right out of his hometown of New York City.

1. “Because of You,” The Ed Sullivan Show (1951)

For Bennett’s debut performance on The Ed Sullivan Show on Sept. 23, 1951, he sang his first No. 1 hit “Because of You.” Originally written by Arthur Hammerstein and Dudley Wilkinson in 1940, “Because of You” was released by Bennett in 1951 and remained on the charts for 31 weeks — 10 of which were at the top.

After his debut on The Ed Sullivan Show, Bennett was invited back a total of 18 times throughout the years and performed “Rags to Riches,” “It Had to be You,” and the Jackie DeShannon hit “What the World Needs Now,” among many more classics.

“Because of You” is also the last song Bennett played on the piano just days before his death at the age of 96 on July 21, 2023.

2. “I Left My Heart in San Francisco,” The Ed Sullivan Show (1964)

During one of his many returns to The Ed Sullivan Show on November 22, 1964, Bennett performed his signature song “I Left My Heart in San Francisco.”

Written by George Cory and Douglass Cross, and released by Bennett in 1962 as a B-side to “Once Upon a Time,” his ode to the City by the Bay remained on the charts for two years and earned Bennett his first two Grammy awards for Record of the Year and Best Male Vocal Performance.

3. “Fly Me to the Moon,” MTV Unplugged (1994)

Recorded on April 15, 1994, at Sony Studios in New York City, Tony Bennett’s MTV Unplugged performance also features special guests k.d. lang and Elvis Costello, and introduced a younger audience to the musical maestro.

Written by Bart Howard, and first recorded by a number of artists, including Frank Sinatra, in 1965 Bennett released “Fly Me to the Moon” on his album, If I Ruled the World: Songs for the Jet Set, and it became a hit for the crooner.

Without a mic, and just a piano backing him, Bennett filled the Unplugged room singing Fly me to the moon / Let me play among the stars / Let me see what spring is like on A-Jupiter and Mars / In other words, hold my hand / In other words, baby, kiss me.

Bennett’s MTV Unplugged live album earned him two more Grammys for Record of the Year and Best Traditional Pop Vocal Performance.

4. “The Way You Look Tonight” with Bill Charlap from New York (2015)

A year before Bennett was diagnosed with Alzheimer’s, he performed a collection of songs, live from New York, with jazz pianist Bill Charlap from their album The Silver Lining: The Songs of Jerome Kern. A collection of composer Kern’s classic pop and theater hits, one of the songs Bennett performed was “The Way You Look Tonight.”

First performed by Fred Astaire in the 1936 film Swing Time, the song also won an Academy Award for Best Original Song, Bennett later recorded the song for his album Long Ago and Far Away in 1958.

The album earned Bennett and Charlap a Grammy for Best Traditional Pop Album in 2016.

5. “I Left My Heart in San Francisco,” Radio City Music Hall (2021)

In celebration of his 95th birthday and to mark his retirement, Tony Bennett gave his final two performances at Radio City Music Hall on Aug. 3 and 5 in 2021, along with collaborator and friend Lady Gaga.

Paired with Lady Gaga, the second night ran through a 27-song set, including “Luck Be a Lady,” “Orange Colored Sky,” Steppin’ Out With My Baby,” and “The Lady is Tramp.” Bennett first recorded the latter song with Gaga for his 2011 album, Duets II. 

In 2021, 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. At 95, Bennett made Grammy history as the second-oldest artist to win the award. Love For Sale followed Bennett and Gaga’s first collaboration, Cheek to Cheek, in 2014, which also picked up a Grammy for Traditional Pop Vocal Album.

For the One Last Time: An Evening with Tony Bennett & Lady Gaga shows, Bennett closed the second night solo at the piano with the final he would ever perform on stage, “I Left My Heart in San Francisco.”

“Tony, we’re all so grateful to have witnessed your talent, your generosity, your creativity, and your kindness, and your service throughout all these years,” Gaga said after his performance. “Mr. Bennett, it would be my honor to escort you off the stage.”

Photo by Tim Mosenfelder/Getty Images