Billie Holiday, Strange Fruit.
Seconded, without regard for the distinctions between jazz and blues.
For my money, the Rev. Gary Davis’ Death Don’t Have No Mercy wins hands down.
Vid of Rev. Davis playing the aforementioned song.
Mance Lipscomb’s version of “Motherless Children” made quite an impression on me. Scary slide guitar–& one of the first bluesmen I heard play in person.
Apparently, Blind Willie Johnson wrote the song. His version is probably darker.
Gotta go with Skip James, “Devil got my woman”.
Wow! Now that is what I call the blues!
I was going to go with something like the whipping post
Answering this question, I admit to a prejudice against ‘slick’, orchestrated, electrified songs – if a man has a chorus of six sequinned girls singing behind him, he may have had the blues at one time, but he ought to be over them by now, dammit.
Son House’s “Death Letter Blues” is a good choice, as are the two Skip James songs nominated so far.
I would add Skip’s “Cypress Grove Blues”, the last verse of which goes:
“When your knee bone’s achin’, and your body’s cold” (2x)
“Then that’s when you’re ready, ready for the Cypress Grove”
How a man who heard music like that managed to go 67 years without killing himself is beyond me.
Although Hank Williams is categorized as country, some of his music is as bluesy as they come. “Ramblin’ Man” is pretty damn bleak:
“And when I’m gone, and at my grave you stand
Just say God’s called home, your ramblin’ man”.
I know blues pretty well, and have been blessed with knowing a lot of great songs by incredible musicians who dealt with awful circumstances by pouring their hearts into the best way possible to try to negate, and overcome, the shit handed them. Many listed here, especially Skip James and Son House.
The other ones, out of so many greats, that make my heart stop, and shudder in the depth of power in their angst: Blind Willie Johnson “Dark Was The Night, Cold Was The Ground”. Not much in lyrics, but down to the depths in a Blues, and Gospel going down to the depths. His “If I Had My Way, I’d Tear This Ol’ Building Down”, is also a tour de force with anger, couching it in Biblical terms, but getting down to the nitty gritty of wanting to change the crap of the status quo.
Sam “Lightning” Hopkins’ Death Bells is another bottom cry.
Seeing this in the last post:
Yep, and how do you think he might have got himself there, then?
He presents some horrific imagery; the above mentioned “Mother is Dead”, the helplessness of the Titanic, and the 1918 Spanish Influenza epidemic. I believe it is “Dark was the Night, Cold was the Ground” that is on the Voyager space probe.
Yes, it was so aching it was chosen to go out and represent us all. Here’s a bit more on that. Also used to sell Trucks in the 90’s.
I love blues. I’m partial to good harp playing. For that you can’t beat Sonny Terry . In this clip he (and partner Brownie Macgee) is playing with that famous bluesman Pete Seeger.
Wow, I came in to mention “Nobody Knows [you] When You’re Down and Out” by Bessie Smith, but…
That wins the thread.
I came to nominate Son House too. Too late, as usual. Guess I got them hung down low down “can’t even get a hard-on” blues.
Gonna go hang myself.
You’re maybe thinking of Robert Johnson’s “Dead Shrimp Blues”? 
Blind Willie Johnson was maybe the greatest acoustic bottleneck slide guitar player of all time, and an absolutlely sincere singer, who, as a Christian, would probably have been insulted to be referred to in the same breath as blues singers. Nonetheless, his “Nobody’s Fault But Mine” (stolen by Led Zeppelin on their ‘Presence’ album) is a virtuoso guitar performance, and as stark a statement as I’ve ever heard on personal responsibility. The true story of his life makes even other blues singers’ lives sound easy.
Well, if he wants to convey the blues, he should get back to us after the girls have deserted him (at which time he’ll sound like Skip James, Son House, or if you favor instrumental expertise, Blind Lemon Jefferson or Blind Blake. Or, whatever you favor, the greatest country blues singer of them all: Charlie Patton).
Until then he’s just another lucky SOB.
Great posts, everyone. Right now, I’d say Rev. Gary Davis’ Death Don’t Have No Mercy wins the thread. Death Letter by Son House is amazing, but it sounds a bit upbeat with that faster steel guitar work.
As bad as these guys?
“Oooooooooooh
The lead’s all gone
The pencil won’t write no mo”
Maybe I’m whooshed, but you do know that song is about impotence, right?
Which only makes it more blue-sy.
Robert Johnson, Me and the Devil Blues:
“Me and the devil was walkin’ side-by-side,
I’m going to beat my woman until I get satisfied.”
…
“You may bury my body down by the highway side,
So my old evil spirit can catch a Greyhound bus and ride.”
That’s the first one I thought of, but after refreshing my memory by listening to it, the tempo was a little more upbeat than I had remembered. I’ve never heard the Blind Willie Johnson version.
Mance Lipscomb could chill your bones with the blues, but he had a wide repertoire. And, as a retired sharecropper, he’d developed a survivor’s mellow philosophy. Lightnin’ Hopkins has been mentioned several times here. But he knew how to laugh, too.
(No, I don’t work for Flower Films.)
And I’d like to add another vote for Hank Williams as a white boy who could get very deep into the blues.