What follows is an attempt to rank the best songs by Francis Albert Sinatra. It is a daunting task and the result is completely biased and, likely, deeply flawed but as you know, if you want to start a conversation in this life, and hopefully, an argument, you can’t just sit there. And besides, if we want to keep the precious music we love, music they don’t make anymore, we need to listen to it and talk about it every day.
There are many different Sinatras and most casual observers only know the Rat Pack version. This won’t do. He is a complex amalgamation of love songs and Big Band numbers and upbeat jazz tunes and saloon stories. He’s Jack Daniels and four (only four) ice cubes, he’s a crisp 100-dollar bill, he’s guys & dolls and love’s first kiss. He’s the personification of personal style and his songs are a priceless treasure and if they were played at a McDonald’s, they would make the place a classy joint.
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I started and stopped this exercise a million times. First I thought I’d rate his albums, but I only own maybe half of them (Sinatra released fifty-nine studio albums and ten more live albums/compilations, not to mention the Rat Pack releases, posthumous box sets, etc.) so that would have been an expensive and complicated road. Then I thought I would rank just the singles he released, there’s 297 of them, but in looking at them I worried that those may not be an accurate representation of his overall body of work and what about the B-sides?
So I started looking at a list of every song he ever recorded, I counted 1,129 of them. I decided to pull out the songs I liked best and I rank them for you here, but there are some things you should know, some disclaimers you should keep in mind and definitions you should consider if we are to have a serious argument here.
So what exactly is a “Sinatra Song?” If you consider songs by other artists, say, a singer-songwriter like Bob Dylan or a rock band like Led Zeppelin, you first identify their songs by their unique styles, but mostly you identify a “Dylan song” or “Zeppelin” by the fact that they wrote it, they made it up. That’s not the case with Sinatra. These 1,129 songs, with the very rare exception, less than ten songs, were written by someone other than Frank. So a “Sinatra Song” is not a song written by Sinatra. What’s more, virtually every one of these 1,129 songs has been recorded by someone else, in most cases, by many, many different artists. So a “Sinatra Song” is not a song recorded exclusively by Sinatra.
To me, the definition of a “Sinatra Song” is abstract and unscientific. It’s simply a song that you hear that is performed with his signature style and that you instantly associate with Sinatra … That’s a “Sinatra Song!” Using the same logic, there are many songs among the 1,129 that just aren’t “Sinatra Songs,” Christmas songs and patriotic songs and traditional tunes (he recorded “Old MacDonald Had a Farm” for example) that you don’t necessarily associate with Sinatra so, with a few exceptions, I don’t rank those songs. Similarly, Frank recorded lots and lots of covers. Later in his career, he recorded numerous popular pop songs by other artists, for example, he recorded “Yesterday.” These aren’t “Sinatra Songs” and I don’t rank them. Also, Sinatra recorded a lot of duets and I mostly pass on these songs, but not always, and there are early recordings that include some heavy-handed background singing which typically detracts from the pure Sinatra-ness of the song, yet there are exceptions, like the songs from the war years that feature the Pied Pipers, many of those songs are wonderful.
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To understand this list you need to understand a little about the arc of Sinatra’s career. Many music historians give the phases of his career names like the “Teen Idol” period or the “Big Band” era. To generalize, I look at his career in three parts: 1) the recordings he did beginning in 1939 and extending into 1953/1954 for Columbia, first with Harry James and ultimately with the Tommy Dorsey Band; 2) the period he spent recording for Capitol Records, roughly from 1953 to 1962; and 3) the remainder of his career that he spent making music with Reprise Records. The earliest period can be associated with Big Band music and at times it sounds like music being played on an old Victrola, the middle period at Capitol is essentially a period of loves songs, so-called torch songs and the more modern years, the Reprise period between 1961 and 1983, produces more jass-influenced songs, songs that the casual fan is most familiar.
The songs included on this list cross the entire Sinatra catalog. There are many, many beautiful love songs, songs you may have never heard before, on the list and I may very well be biased toward these types.
Conversely, when publications like Rolling Stone, put out their “best of” lists they are almost always politically influenced and end up creating lists that will appeal to everyone and no one. They set out to cast the widest net, encompass the most people, they are intentionally politically correct and inclusive. Unfortunately, what they end up with are lists that are totally vanilla, nothing close to the “best of” at all but a list of what is cliché and most popular.
That doesn’t happen here. Songs like “My Way” and “New York, New York” simply aren’t Sinatra’s best songs (and Frank himself was quoted multiple times saying he disliked those songs) so they don’t rank high on the list. The songs that are overexposed and worn out, that have become caricatures of Frank Sinatra himself, those songs, the only songs that some people recognize, don’t rate here. Songs like “Luck Be a Lady” and “The Lady is a Tramp” are just like Metallica’s “Enter Sandman,” overplayed and overrated and nowhere near the best … so they’re nowhere near the list.
The songs on the list are the songs I like the best so I just assume they are the best. Of the 1,129 songs, there are 192 (by my completely unaudited calculation) that Frank recorded more than once. That means that he could have one version of the song that was recorded using a soft, slow beat and a string orchestra, and another totally different rendition using horns and an upbeat jazz arrangement. Depending on which version of a song you’ve heard or are familiar with, you may consider the song great or average, so if you see a song on the list you can’t stand, maybe we have a difference of opinion or maybe you just haven’t heard the right version of the song.
Most of the songs on this list are part of The Great American Songbook, songs written and arranged by the most talented songwriters and lyricists the world has ever known. The bands and orchestras that play the music and the conductors that give it shape are widely considered the best of all-time. So the best songs, in my estimation, are the ones that combine multiple elements: memorable lyrics and themes, magical instrumentation and, of course, performances by The Voice that are emotional and haunting.
Frank Sinatra is an absolute master of phrasing. His inflection, the way he annunciates, the way he begins and finishes a note, the smooth-as-silk way he transitions from one phrase to the next, his exact diction and timing … in this phrasing he has no equal. As such, the songs on this list, the ones that I find unparalleled are the ones that make you say, “Only Sinatra can sing that song in that way.”
In the end, this is a totally subjective journey and, I think, a really fun and interesting one. And it’s a journey embarked upon for only one simple reason, to celebrate the music of Frank Sinatra.
If you recorded 1,129 songs, a good number of them would be lacking in some way. They can’t all be great. Above I listed some reasons as to why certain songs are omitted, I omit others purely because of personal preference. What is left are 133 songs, the best of the best, a work-in-progress, and a tribute to greatness.
Ladies and gentleman, the once-in-a-lifetime musical stylings of Francis Albert Sinatra …
- Strangers in the Night
- Summer Wind
- The House I Live In
- The Girl Next Door
- Somethin’ Stupid
- Witchcraft
- Ring-A-Ding-Ding
- Sunday
- The Best is Yet to Come
- Be Careful, It’s My Heart
- Nancy (With the Laughing Face)
- The Birth of the Blues
- Call Me Irresponsible
- Everything Happens to Me
- Nice ‘n’ Easy
- Nice Work if You Can Get It
- Too Marvelous for Words
- How About You?
- Anything Goes
- I Get a Kick Out of You
- I Thought About You
- I Wish I Were in Love Again
- When I Take My Sugar to Tea
- That’s Life
- I Get Along Without You Very Well (Except Sometimes)
- In the Wee Small Hours of the Morning
- It Was a Very Good Year
- I’ve Got You Under My Skin
- Peachtree Street
- Put Your Dreams Away (For Another Day)
- I Fall in Love Too Easily
- The Best is Yet to Come
- I’ve Got the World on a String
- She’s Funny That Way
- You Make Me Feel So Young
- You’re Getting to Be a Habit With Me
- No One Ever Tells You
- Dancing on the Ceiling
- Don’t Get Around Much Anymore
- Do I Worry?
- The Girl from Ipanema
- You and the Night and the Music
- I’m Gonna Sit Right Down and Write Myself a Letter
- You Might Have Belonged to Another
- Night and Day
- Imagination
- Just One of Those Things
- Last Night When We Were Young
- Until the Real Thing Comes Along
- Can’t We Be Friends
- Blue Skies
- Fly Me to the Moon
- All or Nothing at All
- Five Minutes More
- Laura
- East of the Sun (and West of the Moon)
- Embraceable You
- A Fine Romance
- I Guess I’ll Have to Dream the Rest
- Blues in the Night
- The Way You Look Tonight
- The One I Love (Belongs to Somebody Else)
- (How Little It Matters) How Little We Know
- All This and Heaven Too
- I Can Read Between the Lines
- Oh! Look at Me Now
- I Guess I’ll Have to Change My Plan
- If I Had Three Wishes
- I’ll Never Smile Again
- I’m Beginning to See the Light
- I’ve Grown Accustomed to Her Face
- The Last Dance
- The Brooklyn Bridge
- You’d Be So Easy to Love
- Why Try to Change Me Now?
- I Got It Bad (And That Ain’t Good)
- Learnin’ the Blues
- I Could Write a Book
- Ol’ Man River
- On the Sunny Side of the Street
- Polka Dots and Moonbeams
- Saturday Night (Is the Loneliest Night of the Week)
- Someone To Watch Over Me
- The Song Is You
- Stormy Weather
- Taking a Chance on Love
- What a Funny Girl (You Used to Be)
- We Kiss in a Shadow
- Where or When
- Yes Sir, That’s My Baby
- Just in Time
- That’s Life
- You’d Be So Nice to Come Home To
- Always
- All I Need is the Girl
- (I Got A Woman Crazy For Me) She’s Funny That Way
- I Won’t Dance
- Wrap Your Troubles In Dreams
- They Can’t Take That Away From Me
- Where Are You?
- I’ll Be Seeing You
- I’m a Fool to Want You
- Young At Heart
- It All Depends on You
- It’s Been a Long, Long Time
- Just as Though You Were Here
- Let’s Face the Music and Dance
- Maybe You’ll Be There
- Dolores
- I Think of You
- My One and Only Love
- The Night We Called it a Day
- Little Girl Blue
- That Old Feeling
- There Are Such Things
- There’s No You
- This Love of Mine
- Walkin’ in the Sunshine
- We Three (My Echo, My Shadow, and Me)
- Where is the One?
- You Brought a New Kind of Love to Me
- Hush-A-Bye-Island
- South of the Border
- The Call of the Canyon
- Chicago (That Toddlin’ Town)
- One for My Baby (and One More for the Road)
- The Coffee Song
- I’ve Got a Crush on You
- How Deep is the Ocean?
- I Got a Gal in North and South Dakota
- My Cousin Louella
- A Foggy Day
- Violets for Your Furs