Tony Bennett has been an American icon for over fifty years. It seems very fitting that in his eightieth year on this Earth that ten best songs of his career be looked at.
(1) I Left My Heart in San Francisco I know this is a cliché chose, but no list of Tony Bennett’s best songs is complete without this one. In my book, it is great for only one reason and that reason is that this song was picked as a “filler” song. As the story goes, Tony needed one more song for a concert one evening and someone found this one. It was such a hit with the audience that night and with other audiences that Tony decided to record it. It just goes to show that some of best songs are the ones that weren’t meant to be the big hits.
(2) Steppin’ Out With My Baby- The recording of this song is great, but the version Tony Bennett performed on MTV’s Unplugged is even better. Basically, this song is what cemented Tony Bennett’s “street cred” with Generation X. After thunderous applause, Tony was said to have remarked with the wisdom that only a man born before 1960 would have, “These songs aren’t just old songs, they’re good songs.” For keeping the old way of singing cool is what makes this song great.
(3) I Wanna be Around- This is just another great song. Period. The thing that makes “I Wanna Be Around” great is the pace and punch of it. The opening lines sound like a love and protect type song, but by the punch of the final lyrics, “and that’s when I’ll discover that revenge is sweet. When I sit there applauding from a front row seat,” we know that Tony is kicking the fictional lover of this song while she is down. He sings with such emotion, viciousness and reverie that you support him and don’t hate him for the fact that he wants his ex-love’s heart broken.
(4) The Best Is Yet To Come- Tony actually sang this song before Frank Sinatra and actually Tony’s version is better. The reason being that Tony keeps the song the way it was written, jazzy. Whereas Sinatra sang his version like a lion on the prowl, Tony sang his version like a man in love. And, surprisingly, Tony outshines Frank Sinatra on the clarity of the lyrics; I’ve always felt that Frank wasn’t so clear when he sang his version. Because it is able to outshine Frank Sinatra’s version is what makes this song great.
(5) Fly Me To The Moon- Unlike in his version of “The Best Is Yet To Come” Tony doesn’t outshine Frank Sinatra with this version, but he does equal him. What makes Tony’s version of this song so great is that you can dance to it and that makes it all the more romantic. For the simple fact that Tony decided to keep this one romantic makes it a great song.
(6) Somewhere Over the Rainbow- This song will be forever associated with Judy Garland, but to tell you the truth, I can’t stand her version. It was always sung so slowly and dreamily that it was boring. Typical of Tony Bennett, even though the tempo is basically the same, he sings his version with more optimism. Just listen to it; it’ll make his version of the song your favorite version.
(7) Rags to Riches- One word: optimism. Whenever Tony Bennett sings a song, even a sad song, he exudes optimism. This song talks about all the things he can do with his love by his side and it’s believable. Watch an old clip of him singing this song, the smile on his face is genuine.
(8) New York, New York (duet with Frank Sinatra)- This song belongs to Sinatra and it is only fitting that Tony did a version with Ol’ Blue Eyes himself. For all their competition on the charts, Tony adored Frank. Now Frank had always sung the lyrics with truth, but Tony sings them with knowledge. Their duo powerhouse performance of truth and knowledge of New York City is what makes this version so great.
(9) Stranger In Paradise- This song is just soothing to listen to at night. The vocals are enriching and the song sung with emotion.
(10) How Do You Keep The Music Playing?- Another instance where Tony Bennett outshines Frank Sinatra. Bennett’s version isn’t so much sung as it is talked. It is the poignancy and the intimacy of the reading of lyrics that makes this song so great.
