Sinatra's best sad songs

" I'm A Fool To Want You" has to be one of the most saddest songs, it gets me every time I hear it, heard it the other afternoon on the TV mini series "Sinatra " Frank sat in an aeroplane flying back home from London I think, after another row with Ava.....Heartbreaking.

The album " She Shot Me Down " is a tear jerker too.

He always tells a story in his songs, like he is really feeling it, and you are the only one with him, listening.

 

"I'm a Fool to Want You"

Both the Columbia (1951) and Capitol (1957) recordings are masterpieces. I think it was the Columbia version, with choral backup by the Ray Charles Singers, which was used in the TV mini-series?

Interesting fact about that song, in light of the recent passing of Mitch Miller: "I'm a Fool to Want You" was the A side of the Columbia single produced by Miller which included the infamous dog of a song, "Mama Will Bark." Everyone points to "Mama" as the prime example of how Mitch saddled Frank with poor material, but in reality it was "Fool" that was the bigger hit at a time when his career was fading.

BTW, the song was written for Sinatra, and it is is one of the few tunes for which FS received some writing credits himself due to extemporaneous lyric changes in the studio. (Original lyrics by Jack Wolf; music by Joel Herron.)

 

It's a quarter to three. There's no one in the room except you and me . . .

Better still, find an original clean, mono copy. Bliss.

 

My fave:

 

As much as I love Sinatra's version of 'I am a foool to want you', Billie Holiday OWNED the song when she sang it for the Lady in Satin album.

 

Bobby Darin did a real good cut of this tune.

 

Thanks Bob, I'm not sure which version was used for the mini series offhand.

Maybe Frank was singing "I'm A Fool " to Mitch Miller then.. LOL!

I didn't realise it was the A side to " Mama Will Bark" I've read so many different reviews for this song, but I've only heard it once, on TV in a Bio about Frank.

I remember reading somewhere that Frank had written some of the lyrics specifically for Ava Gardner.

 

The record did not achieve especially large sales (compared to Sinatra's salad days at Columbia years earlier), but both sides made the Billboard chart. "I'm a Fool" reached #14, and "Mama Will Bark" hit #21.

What makes it especially "sad" is that probably more people bought that record than the musically wonderful album, SING AND DANCE WITH FRANK SINATRA, the previous year.

 

Hmmmm....I own both and I have to give the nod to the latest MoFi remaster. My opinion only.

 

Different readings at different points of life make them totally different songs to me. I adore both, BTW.

FYI, it wasn't until they REALLY cleaned up the Columbia version of Mr. S's version for the "Voice in Time" box set that one could hear all the depth and beauty of that recording. For decades it had been a muffled mono mess.

 

Speaking of "I'm a Fool to Want You" and other sad songs, just about every track qualifies on the 1957 Capitol album, WHERE ARE YOU?.

"Lonely Town" is my personal favorite, not just on that album but among Sinatra's sad songs of all time.

 

"Maybe you'll be there" was added to my IPOD and its been in heavy rotation in the last 4 months

 

Supposedly, Frank fled the studio in tears after the final take of the '51 "I'm A Fool." Maybe just an apocryphal story, however....

 

Thanks for reviving this thread, Tina.

On another note, Frank was also a master of the "funny," that is, ironic, or self-deprecating, sad song. These get much less play than his desperate, sober, serious lost love ballads. Among many:

"I Guess I'll Have to Change My Plan"
"Everything Happens to Me" (Dorsey version)
"Can't We Be Friends?"
"The One I Love" (I Remember Tommy version)
"Learnin' the Blues"
"Oh You Crazy Moon"

A very special combination of the ironic/almost funny and the devastated/desperate is "I Guess I'll Hang My Tears Out."

 

A Sinatra song that is sad to me is, "It Was A Very Good Year." Maybe bittersweet is more concise.

 

A couple of others along your line of thought crossed my mind: "Witchcraft" and the version of "It's Only A Paper Moon" from 1950, where he crosses up the chorus with an off-beat delivery. Smiley up-tempo songs about lost love and broken dreams.

 

One Lp said it all:"Watertown",the most Bitter and Saddest Lp He'd ever Recorded,Hands Down!

 

Yes! A VERY quirky (and brilliantly sung) version of a lost-love song.

 

I'd give Only the Lonely the edge over the other desolation LPs (Wee Small, WhereRU?, No One Cares, All Alone, Watertown and SSMD) because Riddle's arrangements match the abject despair of FS's vocals there in a way no other arranger was able to do on the other albums.

Thank God Jenkins was working with Nat Cole at the time and was unavailable to write the charts. No slur on Jenkins, but we would have been deprived of one of the greatest collaborative achievements in the history of American popular music. IMHO, of course....

 

Yes. Or what about "It's A Lonesome Old Town"?

 

It's a stupendous and totally different kind of recording. I think it may even be the greatest studio performance anyone has ever done.

 

It wasn't Gordo who was working with Nat at the time, but rather Nelson was on tour with Cole. Thus, Felix Slatkin conducted the first date.

 

But why didn't Jenkins arrange/conduct? FS had originally pegged him to do it.

 

I'm fairly sure Gordon Jenkins was unavailable when the original project came up. Nelson's absence on the first recording session itself was a different issue which would not have affected the writing of the arrangements themselves.

Apparently (and I'm not sure of the source for this - maybe Peter Levinson's book or Will Friedwald?), Nelson was not the world's best conductor even for his own arrangements(which seems odd - who would know better what was needed from the charts), so the presence of Felix Slatkin as conductor was welcomed. Slatkin, to me, is a bit of an unsung hero in Sinatra's sonic universe. there's an interesting site (if it hasn't been pointed out before) here.

 

You're right, I stand corrected. Nelson was touring the northwest with Cole in late May, but Jenkins, according to Friedwald, was busy in Vegas so the arrangements fell, fortunately to Riddle.