The Year of Tony Bennett

An Appreciation of the Art and Music of Tony Bennett

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Song of the Day: Rules of the Road

The song of the day for Thursday, May 14, 2026, is “Rules of the Road.”

About This Song

“Rules of the Road” was written by Cy Coleman and Carolyn Leigh in 1961. In addition to several recordings by Tony Bennett, the song has also been recorded by Lena Horn, Shirley Horn, Nat King Cole, Anita O’Day, and Rosemary Clooney.

About This Version

Tony Bennett recorded “Rules of the Road” on April 6, 1961, featuring an excellent arrangement by Ralph Burns. It was released on the 1962 album I Left My Heart in San Francisco.

“Rules of the Road,” as well as I Left My Heart in San Francisco, is available on Apple Music.

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Song of the Day: I Left My Heart in San Francisco

The song of the day for Monday, May 4, 2026, is “I Left My Heart in San Francisco.”

About This Song

“I Left My Heart in San Francisco” was written by George Cory and Douglass Cross, who was born 106 years ago on May 4, 1920. Cory and Cross were a gay couple, who met while serving in the Army during World War II, where they wrote shows for their fellow servicemen. After the war, they moved to New York to launch their career as songwriters.

This song is, of course, Tony Bennett’s signature song. It actually became that quite by accident. As Bennett’s musical director, songwriters were constantly giving Ralph Sharon copies of their songs. Cross and Cory had done that and Sharon had stuck the song in a drawer and forgotten all about it. In 1961, he and Bennett were heading out on tour, which included a stop in San Francisco at The Venetian Room at the Fairmont Hotel on Nob Hill. Sharon came across the music and thought it might be a nice local number for the San Francisco audience. After a performance in Hot Springs, Arkansas, they found a piano and started to work on the song a bit. An early fan was the bartender, who said that he’d buy the first copy if they ever decided to record it. Of course, “I Left My Heart in San Francisco” was a huge hit at the performance and in January, 1962, Bennett recorded it and released it on a 45 RPM record on the B-side to “Once Upon a Time.” But gradually, I Left My Heart in San Francisco started getting all the airplay and it became a major hit for Bennett, winning him his first Grammy Award. It is his signature song and is beloved by all of his fans. The San Francisco Giants play Bennett’s recording after every winning home game.

About This Version

Tony Bennett recorded “I Left My Heart in San Francisco” on January 23, 1962, featuring an arrangement by Marty Manning. It was released as a single and was the basis for the album I Left My Heart in San Francisco, released in June 1962.

In 1963, Tony Bennett won two Grammy Awards:

  1. Record of the Year”
  2. Best Solo Performance, Male

Marty Manning won the 1963 Grammy Award for Best Background Arrangement for “I Left My Heart in San Francisco.”

“I Left My Heart in San Francisco,” as well as the album I Left My Heart in San Francisco, is available on Apple Music.

Tony Bennett appeared on the Judy Garland television show and they sang “I Left My Heart in San Francisco.” It was just perfect.

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Song of the Day: Smile

The song of the day for Thursday, April 16, 2026, is “Smile.”

About This Song

“Smile” was written in 1936 by Charlie Chaplin, John Turner, and Geoffrey Parsons for Chaplin’s his last silent film, Modern Times, which shows Chaplin and his costar Paulette Goddard, walking hand-in-hand up the road as the sun sets and as this song plays, in one of the most iconic scenes ever filmed.

About This Version

Tony Bennett recorded “Smile” on June 24, 1959, featuring an arrangement by Ralph Burns. It was released as a single in 1959 and again in 1962 on the album I Left My Heart In San Francisco.

“Smile,” as well as I Left My Heart In San Francisco, is available on Apple Music.

Here is the final sene of Modern Times, with Charles Chaplin and Paulette Goddard.

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Song of the Day: I Left My Heart In San Francisco

The song of the day for Thursday, March 19, 2026, is “I Left My Heart In San Francisco.”

About This Song

“I Left My Heart In San Francisco” was written in 1953 by George Cory and Douglass Cross.

This song is, of course, Tony Bennett’s signature song. It actually became that quite by accident. As Bennett’s musical director, songwriters were constantly giving Ralph Sharon copies of their songs. Cross and Cory had done that and Sharon had stuck the song in a drawer and forgotten all about it. In 1961, he and Bennett were heading out on tour, which included a stop in San Francisco at The Venetian Room at the Fairmont Hotel on Nob Hill. Sharon came across the music and thought it might be a nice local number for the San Francisco audience.

After a performance in Hot Springs, Arkansas, they found a piano and started to work on the song a bit. An early fan was the bartender, who said that he’d buy the first copy if they ever decided to record it. Of course, “I Left My Heart in San Francisco” was a huge hit at the performance and in January 1962, Bennett recorded it and released it on a 45 RPM record on the B-side to “Once Upon a Time.” But gradually, “I Left My Heart in San Francisco” started getting all the airplay and it became a major hit for Bennett, winning him his first Grammy Award. It is his signature song and is beloved by all of his fans.

About This Version

Tony Bennett recorded “I Left My Heart In San Francisco” on January 23, 1962, which was released as a single. Marty Manning wrote the arrangement and conducted the orchestra. The song was added to the album I Left My Heart In San Francisco, which was released in June 1962.

Tony Bennett won two Grammy Awards at the 5th Annual Grammy Awards for “I Left My Heart In San Francisco.”

  • Record Of The Year
  • Best Solo Performance, Male

“I Left My Heart In San Francisco,” as well as I Left My Heart In San Francisco, is available on Apple Music.

Dear Mr. Bennett

Tony Bennett sang “I Left My Heart In San Francisco” at every concert of his I attended. I’m 99% sure he sang it at every concert he gave after winning the record of the year Grammy Award.

The John Pizzarelli Trio (Pizzarelli on guitar and vocals, Michael Karn on bass, and Isaiah J. Thompson on piano) recorded “I Left My Heart In San Francisco” for Dear Mr. Bennett, released in March 2026.

Dear Mr. Bennett is available for purchase on CD and vinyl at Amazon, Barnes and Noble, Tower Records, and other record stores. It is also available on most popular streaming services.

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Song of the Day: Once Upon a Time

The song of the day for Friday, January 23, 2026, is “Once Upon a Time.”

About This Song

“Once Upon a Time” was written by Charles Strouse and Lee Adams for the 1962 Ray Bolger musical All American, where it was introduced by Bolger and Eileen Herlie. While the musical was not a major smash hit, the song is quite lovely. In addition to Tony Bennett’s fine recording, it was also recorded by Frank Sinatra, Andy Williams, Howard Keel, Bobby Darrin, and Mandy Patinkin.

About This Version

Tony Bennett recorded “Once Upon a Time” 64 years ago on January 23, 1962; “I Left My Heart in San Francisco” was recorded on the same day as well. “Once Upon a Time” was released on the A-side of single, with “I Left My Heart in San Francisco” on the B-side. Marty Manning wrote the arrangement and conducted. Both songs were released later that year on the album I Left My Heart in San Francisco.

“Once Upon a Time,” as well as I Left My Heart In San Francisco, is available on Apple Music.