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Top 10 Tony Bennett Songs

His Best Recordings


Tony Bennett was born Anthony Benedetto in New York City in 1926. He faught in the US Army in World War II, and decided to pursue a music career upon returning home. Tony Bennett was signed to Columbia Records by Mitch Miller in 1950. Pearl Bailey suggested that he shorten his given name to Tony Bennett. His first #1 pop hit was "Because Of You" in 1951. Tony Bennett continues recording today in his 80s. These are his 10 best signature recordings.

1. "I Left My Heart In San Francisco" (1962)

Courtesy Columbia Records

"I Left My Heart In San Francisco" is a pop landmark. It was written in 1953 by songwriters and lovers George Cory and Douglas Cross. They wrote the song in a nostalgic mood for their home city of San Francisco while living in New York. If it wasn't for their constant pestering of Tony Bennett's music director Ralph Sharon, this glorious recording would have never existed. Tony Bennett recorded "I Left My Heart In San Francisco" in January 1962. It was released by Columbia Records and only peaked at #19 on the Billboard Hot 100. However, "I Left My Heart In San Francisco" appealed strongly to fans of a more adult sound. It was certified gold for sales and won the Grammy Award for Record of the Year. Soon, the city of San Francisco adopted it as an official song. The Target special edition of Tony Bennett's Duets album includes a version of the song performed with Judy Garland.

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2. "The Shadow Of Your Smile" (1965)

Tony Bennett - Movie Songs
Courtesy Columbia Records

The subtle artistry of Tony Bennett's singing through quiet moments in a ballad is perhaps no better demonstrated than on this 1965 recording. "The Shadow Of Your Smile" was first introduced as a trumpet solo in the 1965 film The Sandpiper. The beauty of the song was quickly noticed and recorded by a wide range of artists including Barbra Streisand and Frank Sinatra. "The Shadow Of Your Smile," as sung by Tony Bennett, won the Grammy Award for Song of the Year. It also won the Academy Award for Best Original Song. Tony Bennett recorded "The Shadow Of Your Smile" in a duet with Colombian singer Juanes on his album Duets.

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3. "Stranger In Paradise" (1953)

Tony Bennett - Alone At Last
Courtesy Columbia Records

"Stranger In Paradise" was introduced in the 1953 musical Kismet. The melody is borrowed from composer Alexander Borodin's Polovtsian Dances. A wide range of artists recorded the song, but it is Tony Bennett's version that was the biggest hit. Tony Bennett's "Stranger In Paradise" hit #1 in the UK in 1953 and was named the top selling song in the US by Cashbox for two different weeks. The durable melody will be instantly familiar to a wide range of pop music fans. Tony Bennett recorded a "Stranger In Paradise" duet with Andrea Bocelli for his album Duets II.


4. "Because Of You" (1951)

Tony Bennett - Solitaire
Courtesy Columbia Records

"Because Of You," released in 1951, was Tony Bennett's first #1 pop hit. It remained on top for 10 weeks. The song was written in 1940 and used in the 1951 film I Was An American Spy. "Because Of You" has a warmly nostalgic style of a bygone era. Tony Bennett recorded the song with k.d. lang for his album Duets.


5. "The Good Life" (1963)

Tony Bennett - The Good Life
Courtesy Columbia Records

Tony Bennett reached #18 on the Billboard Hot 100 with his 1963 recording of "The Good Life." It has become one of Tony Bennett's signature songs and is the title of his 1998 autobiography. "The Good Life" has a grand, swinging feel. Tony Bennett recorded "The Good Life" with Billy Joel for his album Duets.


6. "The Best Is Yet To Come" with Diana Krall (2006)

Tony Bennett - Duets
Courtesy Columbia Records

It is difficult for the more recent duet versions of these signature songs to match Tony Bennett's original versions. However, the swinging arrangement of "The Best Is Yet To Come" recorded with Diana Krall for the Duets album is stellar. The song was first introduced in 1962 on Tony Bennett's I Left My Heart In San Francisco album.

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7. "Rags To Riches" (1953)

Tony Bennett - Rags To Riches
Courtesy Columbia Records

"Rags To Riches" was written by Richard Adler and Jerry Ross and recorded and released by Tony Bennett in 1953. It went to #1 on the pop singles chart. The song became familiar to a new generation through its inclusion in the opening sequences of the 1990 film Goodfellas. Tony Bennett recorded "Rags to Riches" with Elton John for his album Duets.


8. "Smile" (1959)

Tony Bennett - All-Time Greatest Hits
Courtesy Columbia

"Smile" first appeared as an instrumental theme in Charlie Chaplin's 1936 film Modern Times. English lyricists John Turner and Geoffrey Parsons added lyrics and a title to the song in 1954. Nat King Cole had the first hit with the song in 1954. Tony Bennett released his version of "Smile" in 1959 and had a minor hit with it. More recently, the song was recorded by Michael Jackson. Jermaine Jackson sang the song at the Michael Jackson memorial service. Tony Bennett recorded a duet with Barbra Streisand on the song for his album Duets.


9. "Blue Velvet" (1951)

Tony Bennett - Blue Velvet
Courtesy Columbia Records

"Blue Velvet" was written in 1950 and Tony Bennett recorded the first hit version in 1951. He took the song to #16 on the pop singles chart. His trailing run on the word "velllvet" set a standard for the song. Bobby Vinton took the song to #1 in 1963. "Blue Velvet" also inspired the David Lynch film of the same name. Tony Bennett recorded "Blue Velvet" with k.d. lang for his album Duets II.


10. "In the Middle Of an Island" (1957)

Tony Bennett - In the Middle Of an Island
Courtesy Columbia Records

"In the Middle Of an Island" is not a particular personal favorite of Tony Bennett's, and he rarely performs it in concert. However, it was his last top 10 hit reaching #9 in 1957. It does represent a more uptempo, novelty oriented sound for Tony Bennett. It is a carefree, romantic tune.


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