Top Ten Songs by Frank Sinatra

Francis Albert Sinatra is a national treasure in the United States of America. He took the art of popular singing and made it something new. Before him, if it wasn’t opera than it wasn’t music. Sinatra made every song he sang a classic for either good or bad reasons. The following ten songs are the best of his whole career:

(1) All or Nothing At All (w/ Harry James Orchestra-1939)- I truly believe that without this song, nobody would ever be able to talk about a man named Frank Sinatra. Besides the fact that this is the first song to introduce Frank Sinatra to people outside of New Jersey, this song is just damned good. The lyrics have always been about “puppy-love” and the young, inexperienced voice of 24 year old Frank Sinatra give the song that mood. He literally sounds like a high school kid who is trying to woo his girl by singing and pleading with her over the telephone. The music is also great, because the slightly swinging ballad is a sound Sinatra would adopt for years to come.

(2) I’ve Got the World on a String (1953)- If anything captures the mood of Frank Sinatra after winning his oscar for From Here to Eternity and for getting a new record contract with Capitol Records, it is this song. This song is great because it is the new version of Sinatra in complete comeback mode. When he sings, “I’ve got the world on string, sittin’ on a rainbow” the audience immediately believes it. Other singers may have covered the song, but Sinatra owned it. With a great arrangement by Nelson Riddle, a man instrumental in the new Sinatra sound, this song is just priceless.

(3) I’ve Got You Under My Skin (1956)- It has been noted by a lot of people that Sinatra’s second wife, Ava Gardner, taught him how to really sing a torch song. This isn’t to say that he took lessons from her, but it’s just that his intense love and longing for the woman taught him how to put that raw emotion into a song. This song lets all that raw emotion out. When he sings, “I said to myself this affair never will go so well, but why should I try to resist when baby I know so well, cause I’ve got you under my skin” the listener can just picture Sinatra saying this to Gardner in person. Also, this is just the best version of the Cole Porter classic.

(4) One For My Baby (1958)- Sinatra always described himself as a saloon singer. When you listen to this song, you realize he wasn’t being humble about what he thought his true talents were, he was just being right. If “I’ve Got You Under My Skin” is pleading with Ava Gardner, than “One For My Baby” is pleading with the bartender to help him forget Ava Gardner. Through the whole song he keeps saying to just listen to him and he’ll tell you the story, but he ever does. Yet, because this is Sinatra at his finest we already know the story and understand completely.

(5) Nice ‘n’ Easy (1960)- This song shows the transition of the Swinging Sinatra of the Capitol Records/1950s era to the Chairman of the Board of the Reprise Records/1960s era. The great thing about this song is that it doesn’t even sound likes he trying; it sounds as if he walked up the microphone, read the lyrics and walked away. This is the beauty of Sinatra, he knew that the feeling of the song was “Nice ‘n’ Easy” and he sang it just that way.

(6) Pennies from Heaven (1962)- Sinatra did a perfectly good rendition of this song in 1956, but this 1962 version just takes the cake. Like “Nice ‘n’ Easy” the arrangement starts off with Sinatra not even sounding like he’s trying, but by the second time around he is really swinging and swinging hard. With Count Basie’s band behind him, he couldn’t have possibly lost.

(7) Softly As I Leave You (1965)- This is a song Sinatra should have sang when he tried to retire in 1970. The song is sappy and isn’t really that good, but Sinatra, as usual, makes it great. It just be because of the emotion he puts into the song. He’s loved and left so many by the time he sang this song, he just knows how to sing it.

(8) That’s Life (1966)- If I didn’t mention this song, then I wouldn’t be a true Sinatra fan. If any song should have been his “national anthem” then it should have been this one and not “My Way.” Unlike “My Way,” this song isn’t boastful, but realistic. It talks about nothing but surviving and this is something Sinatra knew how to do.

(9) Bad, Bad Leroy Brown (1973)- I have to say I actually like this song. I know some call it a rape of great song by Jim Croce, but I feel that Sinatra knew the characters in the song better than Jim Croce did. It’s just one of those songs that you knew Sinatra ddidn’t think was all that great, but he had great fun singing it. If you want to see the best version of his rendition of the song, watch The Main Event concert at Madison Square Garden.

(10) How Do You Keep The Music Playing? (1983 or 85, can’t remember)- This is the question that many Sinatra fan have asked themselves since the great man’s passing in 1998. This is possibly the most beautiful love song Sinatra ever sang. By this time, he was a senior statesman in show business and in life and he knew how to sing the hell out of this song. Also, the arrangement is just extraordinary. This is the only reason I still listen to the album “L.A. Is My Lady.”

Well, those are the best songs of the best singer in American history. Some may agree and others just won’t and they’ll have their own opinions. Anyways, these were the top ten of his career.

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