Top 10 Tony Bennett Songs Of All Time

Tony Bennett Performs At The Royal Albert Hall
Samir Hussein / Getty Images

Tony Bennett was born Anthony Benedetto in New York City in 1926. He fought 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 90s. These are his 10 best signature recordings.

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

"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. Tony Bennett says of it, "That song helped make me a world citizen. It allowed me to live, work, and sing in any city on the globe. It changed my whole life." 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 2006 Duets album includes a version of the song performed with Judy Garland.

Tony Bennett has performed "I Left My Heart In San Francisco" live for a number of special occasions. He sang it at the 50th-anniversary celebration of the Golden Gate Bridge in 1987, at the reopening of the San Francisco-Oakland Bay Bridge after the 1989 Loma Prieta earthquake, during the 2002 and 2010 World Series featuring the San Francisco Giants, and at the 2012 San Francisco Giants World Series parade.

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"The Shadow Of Your Smile" (1965)

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 it was recorded by a wide range of artists including Barbra Streisand and Frank Sinatra. Johnny Mandel, writer of "Suicide Is Painless," the theme from M*A*S*H, co-wrote "The Shadow Of Your Smile" with three-time Academy Award winner Paul Francis Webster. "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. The American Film Institute has listed it as one of the top 100 movie songs of all time. Tony Bennett re-recorded "The Shadow Of Your Smile" in a duet with Colombian singer Juanes on his 2006 album Duets.

"The Shadow Of Your Smile" was never a major pop hit. Tony Bennett's version reached the top 10 on the adult contemporary chart but only #95 on the overall pop singles chart. In 1966 Johnny Mathis barely scraped the lower reaches of the chart with his version of the song.

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"Stranger In Paradise" (1953)

"Stranger In Paradise" was introduced in the 1953 musical Kismet. Richard Kiley and Doretta Morrow performed the original cast version of the song. Vic Damone and Ann Blyth performed the song in the movie. The melody is borrowed from composer Alexander Borodin's Polovtsian Dances from the opera Prince Igor. 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 2011 album Duets II.

Beyond Tony Bennett's big hit version of "Stranger In Paradise," five other recordings hit the top 20 on the UK pop singles chart. They included vocal recordings by the Four Aces, Tony Martin, Bing Crosby, and Don Cornell in addition to an instrumental recording by Eddie Calvert. 

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"Because Of You" (1951)

"Because Of You," released in 1951, was Tony Bennett's first #1 pop hit. It remained on top for eight weeks. Johnny Desmond had a top 20 hit with his concurrent recording of "Because Of You." Tab Smith recorded an R&B instrumental version in 1951 that topped the R&B chart. The song was written in 1940 and used in the 1951 film I Was An American Spy. Arthur Hammerstein, the uncle of Oscar Hammerstein II, co-wrote "Because Of You" with Dudley Wilkinson. The song has a warmly nostalgic style of a bygone era. Tony Bennett re-recorded "Because Of You" with k.d. lang for his 2006 album Duets.

"Because Of You" has been recorded by other mainstream pop artists. Connie Francis recorded it in 1959. Neil Sedaka recorded it in 1964, but his version was not released until 2005. Rock artist Donnie Iris released a single version of "Because Of You" in 1979 but it failed to chart.

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"The Good Life" (1963)

Tony Bennett reached #18 on the Billboard Hot 100 with his 1963 recording of "The Good Life." The song was co-written by French songwriter Sacha Distel. 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. It is included on Tony Bennett's 1994 MTV Unplugged album, and he re-recorded "The Good Life" with Billy Joel for his 2006 album Duets.

In 1971, singer Tony Orlando recorded a version of "The Good Life" as the theme song for a sitcom of the same name starring Larry Hagman. The show was canceled in the middle of its first season after 15 shows aired.

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

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. "The Best Is Yet To Come" was written by Cy Coleman and Carolyn Leigh in 1959. They had a turbulent songwriting partnership but also wrote "Witchcraft," a hit for Frank Sinatra and Grammy Award nominee for Song of the Year. Frank Sinatra also recorded his own version of "The Best Is Yet To Come" in 1964 and the title is inscribed on his tombstone. It was the last song he sang in public in 1995.

On May 22, 1969, "The Best Is Yet To Come" was played as the wake-up call for the crew of Apollo 10 while orbiting the moon. 

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"Rags To Riches" (1953)

"Rags To Riches" was written by Richard Adler and Jerry Ross, composers of the musicals The Pajama Game and Damn Yankees, and recorded and released by Tony Bennett in 1953. It went to #1 on the pop singles chart for eight weeks and earned a gold record certification for sales. Elvis Presley took "Rags To Riches" back to the pop top 40 in 1971. The song became familiar to a new generation through its inclusion in the opening sequences of the 1990 film Goodfellas. Tony Bennett re-recorded "Rags to Riches" with Elton John for his 2006 album Duets.

Two other versions of "Rags To Riches" released in 1953 along with Tony Bennett's version were significant hits. Billy Ward and His Dominoes recorded the song and reached #2 on the R&B singles chart. David Whitfield recorded it and hit #3 on the UK pop singles chart. Barry Manilow included "Rags To Riches" on his The Greatest Songs of the Fifties album.

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"Smile" (1959)

"Smile" first appeared as an instrumental theme in Charlie Chaplin's 1936 film Modern Times. The actor composed the music with inspiration from the Puccini opera Tosca. English lyricists John Turner and Geoffrey Parsons, who are also credited with "Oh! My Pa-Pa" added lyrics and a title to the song in 1954. Nat King Cole had the first hit with the song in 1954. He climbed to #10 on the US pop singles chart and #2 on the UK chart.

Tony Bennett released his version of "Smile" in 1959 and had a minor hit with it peaking at #73. Comedian Jerry Lewis used "Smile" as the theme song for his late 1960s TV show. More recently, the song was recorded by Michael Jackson and included on his album HIStory: Past, Present and Future Book 1. It was scheduled to be released as a single but canceled at the last minute. Jermaine Jackson sang the song at the Michael Jackson memorial service. Tony Bennett recorded a duet version of "Smile" with Barbra Streisand on his 2006 album Duets.

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"Blue Velvet" (1951)

"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 runs on the word "velvet" set a standard for the song. It has been covered by multiple artists. Two vocal groups, the Clovers and the Statues, took "Blue Velvet" into the charts in 1955 and 1960 respectively. Bobby Vinton took the song to #1 in 1963. It served as another "blue" song to follow up his top 3 hit "Blue On Blue." "Blue Velvet" also inspired the David Lynch film of the same name. Tony Bennett re-recorded "Blue Velvet" with k.d. lang for his album Duets II in 2011. Lana Del Rey released a cover of "Blue Velvet" in 2012 as part of her EP Paradise.

The inspiration for writing the song "Blue Velvet" occurred when songwriter Bernie Wayne was visiting friends in Richmond, Virginia and stayed at the Jefferson Hotel. He saw a woman at a party that brought the song's first line, "She wore blue velvet," to mind.

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"In the Middle Of an Island" (1957)

"In the Middle Of an Island" was Tony Bennett's final top 10 pop hit reaching #9 in 1957. It represents a more uptempo, novelty oriented sound for Tony Bennett. It is a carefree, romantic tune co-written by Nick Acquaviva, co-writer of Joni James' top 10 1953 hit "My Love, My Love," and Ted Varnick. Country star "Tennessee" Ernie Ford also recorded "In the Middle Of an Island" in 1957 and made a minor dent on the pop chart reaching #56.

Tony Bennett stated in an interview that "In the Middle Of an Island" was one of his least favorite songs. He said, "To my great annoyance, it actually got into the top ten. But I've never received one request for that song in all the years I've been performing since. That was the last time I sang something I really couldn't stand."