Tony Bennett's 10 greatest songs ever, ranked

21 July 2023, 16:50

Tony Bennett had one of the most iconic voices in music, and many of his songs are considered part of the Great American Songbook.
Tony Bennett had one of the most iconic voices in music, and many of his songs are considered part of the Great American Songbook. Picture: Getty

By Thomas Edward

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Tony Bennett had one of the most iconic voices in music.

Throughout his storied career, Tony Bennett has amassed numerous awards because of his effortlessly rich voice and laidback charm.

He possessed a voice that immediately transports you back in time to the golden age of Hollywood, show business, and romance.

That's precisely why Bennett has continued to appeal to new generations, gaining another legion of fans during the MTV era and showed his dedication to working with new talent when he collaborated with the likes of Paul McCartney, Lady Gaga, John Legend, and Amy Winehouse.

Though his comparisons to Frank Sinatra remained, Tony Bennett was a singular voice in jazz, big band, swing, and traditional pop music.

Talking about her friend and collaborator, Lady Gaga said in 2021: "He is a remarkable human being - he served our country, he also marched with Dr Martin Luther King Jr., he used to sneak Duke Ellington into the back of his hotels to play jazz music all night long."

"His commitment to civil rights, and to humanity, is something that he has taught me from a young age to take with me in all that I do. I love him very deeply."

Nothing truer can be said about his many fans around the world too. That said, here are the ten greatest Tony Bennett songs, ranked:

  1. 'If I Ruled The World'

    Tony Bennett (feat. The Woody Herman Orchestra) "If I Ruled The World" on The Ed Sullivan Show

    Originally a number from the 1963 West End play Pickwick, 'If I Ruled The World' took on a new life when Tony Bennett put his spin on it.

    He later revisited the song in 2006, duetting with Celine Dion for his album Duets: An American Classic.

    Over the years the likes of Stevie Wonder, James Brown, The Supremes, and Tom Jones have all covered it, but Tony's is the version that people remember.

  2. 'Cold, Cold Heart'

    Tony Bennett - Cold, Cold Heart (from Viva Duets)

    A country music song written by Hank Williams, 'Cold, Cold Heart' was Tony Bennett's second number one single.

    Considered as a key entry in the 'Great American Songbook', Bennett brought the iconic song to a mainstream audience with his orchestral take on the country classic.

  3. 'Something'

    Tony Bennett - Something

    Tony wasn't afraid to put try out newer pop songs in his swing style, and The Beatles' 'Something' was one of them.

    Most definitely one of the George Harrison penned songs which was primed to be translated into different genres and generations, Bennett recorded his version in 1970.

    Only a year after its initial release on The Beatles' Abbey Road, Bennett helped reiterate the song's timelessness, encouraging covers from countless artists afterwards.

  4. 'Stranger In Paradise'

    Tony Bennett "Stranger In Paradise" on The Ed Sullivan Show

    'Stranger In Paradise' was another song taken from a musical play - this time it was Kismet, and Bennett made it a worldwide hit in 1952.

    Though it narrowly missed out on the top spot in the US charts upon its release, it peaked at No.1 in Australia which transformed Bennett into an international star.

  5. 'The Good Life'

    The Good Life

    Bennett's international streak continued in 1963 when he recorded the French song 'La Belle Vie' by Sacha Distel.

    The English translation being 'The Good Life', Tony's recording became the definitive English-speaking version of the song, and was a staple of his sets throughout the remainder of his glittering career.

    It's been in constant circulation on movies and adverts since its release because Bennett's warm, positive singing on the song.

  6. 'Fly Me To The Moon'

    Tony Bennett - Fly Me to the Moon (In Other Words) (Live on MTV Unplugged)

    An absolute giant of jazz music songwriting because of its association with space exploration in the 1960s, it is often Frank Sinatra's version which springs to mind when hearing the opening lyrics.

    But Tony Bennett's cover of 'Fly Me To The Moon' - recording it a year after Sinatra - was widely considered a rival to Frank's smooth classic.

    His definitive version was during his MTV Unplugged session, where he puts the microphone down and sings completely a-cappella.

  7. 'The Way You Look Tonight'

    Tony Bennett, Bill Charlap - The Way You Look Tonight (Live in New York - August 2015)

    Tony Bennett underwent a career resurgence during the 1990s, and his rendition of 'The Way You Look Tonight' was the moment his popularity peaked once again.

    Featuring in the 1997 Julia Roberts' rom-com My Best Friend's Wedding, Tony's classy version of the 1936 Fred Astaire classic endeared him to a whole new audience of younger kids pining for a bygone era.

  8. 'Rags To Riches'

    Rags To Riches

    'Rags To Riches' was Tony Bennett's third number one single in the US, staying at the top spot for a total of eight weeks, but was also his last.

    Quite remarkable for an artist who maintained a successful career for seventy more years that he'd never hit the top spot once again.

    Written by Richard Adler and Jerry Ross in 1953, they contributed many entries into the Great American Songbook before Ross' tragic death two years later at the age of 29 which curtailed their promising career.

    Bennett did the pair justice with his iconic voice however, telling the story of someone going from "rags to riches" which has since been used in countless adverts and films such as Martin Scorcese's Goodfellas.

  9. 'Because Of You'

    Tony Bennett "Because Of You" on The Ed Sullivan Show

    Bennett quite literally burst onto the scene as a singer with debut single 'Because Of You' which went straight in at number one in the US charts.

    It was the song that made Tony Bennett a bonafide musician, and started his long and illustrious career.

    He never forgot about the sentiment of the song and the success it gave him, continually singing it throughout the years, including his final ever live concert seventy years after the song first hit the airwaves.

  10. 'I Left My Heart In San Francisco'

    Tony Bennett - I Left My Heart In San Francisco (One Last Time: Live At Radio City Music Hall 2021)

    'I Left My Heart In San Francisco' is often considered to be Tony Bennett's signature song, and is undoubtedly his greatest.

    Written by amateur songwriters George Cory and Douglass Cross, the song was intended to a number of artists before making its way to Bennett who fell in love with the song's sentiment whilst on his way to perform in San Francisco himself.

    In 1984, the song was adopted by the City and County of San Francisco as the city's official anthem, and Bennett was later awarded a Towering Performance Award by the Songwriters Hall Of Fame because of his iconic performance.

    It was the signature song of a singer that embodied class, romance, and sheer talent.