Song of the Day #3,367: ‘One for My Baby (and One More for the Road)’ – Frank Sinatra

After trotting out the songs that make us happy yesterday, you might have predicted that today’s installment of the 30 Day Music Challenge would call for ‘A Song That Makes You Sad.’

As a self-professed lover of melancholy music, I have no shortage of songs to choose from today. Many of my favorite artists (think Aimee Mann and Belle & Sebastian) are known for writing sad songs. But I decided to reach back to a classic from well before my time.

Frank Sinatra’s Only the Lonely is a broken-hearted masterpiece, a collection of torch songs that Ol’ Blue Eyes named as his favorite of his albums.

Album closer ‘One for My Baby (and One More for the Road)’ wraps things up with a tear-soaked elegance nobody can deliver like Sinatra.

It’s quarter to three, there’s no one in the place except you and me
So, set ’em up, Joe, I got a little story you oughta know
We’re drinkin’, my friend, to the end of a brief episode
Make it one for my baby and one more for the road

I got the routine, so drop another nickel in the machine
I’m feelin’ so bad, wish you’d make the music pretty and sad
Could tell you a lot, but you’ve got to be true to your code
So, make it one for my baby and one more for the road

You’d never know it but buddy, I’m a kind of poet
And I got a lot of things to say
And when I’m gloomy, you simply gotta listen to me
Till it’s all talked away

Well that’s how it goes and Joe, I know your gettin’ pretty anxious to close
So, thanks for the cheer, I hope you didn’t mind my bendin’ your ear
This torch that I found must be drowned or it soon might explode
So, make it one for my baby and one more for the road
That long, long road

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10 thoughts on “Song of the Day #3,367: ‘One for My Baby (and One More for the Road)’ – Frank Sinatra

  1. Rob says:

    I’ve a lean for melancholy as well, and I could probably list 100 sad songs without blinking an eye. But I won’t. I will however provide “American Trilogy” by Micky Newbury. He strung three American classic songs into one, at a time when race riots were rampant. According to lore, he performed this in LA at The Troubadour in ’72, and there wasn’t a dry eye in the house. Elvis Presley used this in his live show, and his band turned it up several notches and turned it into a bombastic showstopper. However, I prefer Newbury’s original version. It never fails to stop me in my tracks. His voice sends shivers down my spine. If you like this, find Newbury’s “San Francisco Mabel Joy” – a gut-wrenching song.

  2. Peg Clifton says:

    Funny I just chose One for my baby for the drug/alcohol song. I agree Sinatra is the king of torch songs. I’m going with the Watertown album -yes the whole album especially the final song.

  3. Dana Gallup says:

    Not to quibble with your selection, but it seems you picked a sad song rather than a song that makes you sad. There is, of course, a difference. To me, a song that makes you sad presses on your personal experiences and emotions, rather than a song with a melancholy tone or lyrics that you like or enjoy because, in your case, you’re into that sort of thing.

    So, for my pick, I am going to go with a song that truly makes me so sad that I rarely play it even though it’s a beautiful song. When my mother was in the final months of her life in the hospital, we brought in a portable CD player and a handful of CDs she liked. One of them was Nora Jones’ album Come Away with Me. Many a day after visiting mom, I would ask her if she wanted me to put music on before I left. She usually said yes, and I usually put Jones’ album on. As I kissed her goodbye and walked out of the room, the opening track “Don’t Know Why” would begin playing. Each time, as I left her with the song playing, I thought to myself how few days I really had left with her and worried that she would no longer be with us the next time I returned, particularly if, for whatever reason, a day or more passed without a visit because of some other thing going on in my life. So, hearing the lyric”Don’t know why I didn’t come…” filled me with sadness and guilt and regret. After mom died, I found it almost impossible to hear the song when it would come on the radio or pop up on iTunes. Not only would it fill me with sadness about her passing, but it would immediately transport me back to her hospital room and fill me with guilt that I should have been there more, should have done more. I will share the song here, but I won’t be playing it as it is still too painful even twelve years later.

  4. Doug says:

    You can’t argue with that selection, though I’d have gone with the album’s first cut– “Only the Lonely.” It addresses Dana’s objection. If you ain’t saddened by this one you can’t be saddened. And a good argument could be made for Mom’s choice, the closer on the Watertown album. It puts a blister on your heart.

  5. Madison says:

    I’m not sure if this bends the rules a bit, but Broadway songs are really the ones which can actually make me cry/sad. I was most directly between “One Last Time” (currently mourning the devolution of class act American politics) and “It’s Quiet Uptown.” Realistically, a song mourning the loss of a child wins out. https://m.youtube.com/watch?v=rrsmUzqweBI

  6. Amy says:

    The song ” A Long December” by the Counting Crows is one I love and listen to still, despite the fact that it always makes me sad. It was a song I heard often during the time Selma was sick, so the lyrics resonate deeply.

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