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Analytical Commentary
Who is the Jokerman? This commentary proposes that the Jokerman is Dylan the Jew: An individual blessed with charisma and cursed with turbulence, aware of God's commands but unsure of their reality and of his ability to respond. Is this Dylan the Jew before Jesus or after Lubavitch? I believe the latter.
Standing on the water... while the eyes of the idol: To understand this song, it is important to separate the Jokerman who is "standing on the water" from all that is going on around him. The world of the Jokerman -- of all of us in the late 20th century -- is full of idols with iron heads, stalkers, molotov cocktails, men placing orphans at the feet of harlots. Amid this chaos stands the Jokerman, with great power and greater confusion.
Jokerman LyricsBiblical Commentary
Thanks to Susan Isserman for the insight and inspiration
Your bread: A key principle by which Dylan is interpreted is that "you" and "he" is Dylan, singing to himself, about himself. Standing on the water
Casting your bread
While the eyes of the idol with the iron head
Are glowin'
Cast your bread upon the waters, for you shall find it after many days (Ecclesiastes 11:1). There is faith in this, but it is a different, less intense, wiser faith than that of the God-intoxicated ba'al teshuva, the born-again penitent. It is a faith that good deeds will be repaid in kind -- but with a hint of doubt as well. "Thou knowest not the the works of God who makes all," cautions Ecclesiastes, the preacher in Jerusalem, four verses later.
Born with a snake: Microphones in his fists, the emblems of Dylan's power as a central figure in American culture in the generation following the war -- the hurricane -- the Holocaust -- which raged at his birth. Distant ships sail into the mist
You were born with a snake in both of your fists
While a hurricane was blowin'
Just around the corner from you
But with truth so far off
What good will it do
The setting sun has religious significance in Judaism. Sunset marks the time for evening prayers. Sunset marks the transition to, or from, the Sabbath or holiday.

Rabbi Joseph B. Soloveitchik, may his memory be for a blessing, used a sunset to exemplify the head space of the "Halachic Man" -- someone living, breathing, thinking the categories of Jewish law -- in contradistinction to an artist or scientist. A scientist, he wrote, sees the sun set and observes the scattering of light through the atmosphere and the operations of orbital mechanics. An artist sees the interplay of color and light. And the Halachic man sees the obligation to pray.

When the sun sets on Saturday evening, you rise up and say goodbye to the Sabbath. To no one? Well, there's nobody there, nothing real, nothing concrete. Is this a befuddled description of Jewish practice by a naive narrator? Is this a Christian mocking Jewish rituals? Or is this the song of someone observing the Sabbath and the parting havdalah ritual, but full of doubt and uncertainty?

Jokerman dance to the nightingale tune
Bird fly high by the light of the moon
Oh, Jokerman
So swiftly the sun
Sets in the sky
You rise up and say goodbye
To no one.
Fools and angels: The dualities that Dylan has again discovered inside himself. Both of their futures could be his as leaves behind the Christian certitudes, shedding off one more layer of skin. Fools rush in where angels fear to tread
Both of their futures
So full of dread
You don't show one.
Shedding off one more layer of skin
Keeping one step ahead of the persecutor within.
The story of Jacob is alluded to very strongly in this stanza. Jacob wrestled with the angel; he is called "ish tam" -- a simple man, a fool. Both of their futures, Jacob and twin Esau. The layer of goat skin Jacob wrapped on his arm to fool his father as he cheats his brother out of the blessing. Running in flight, watching the angels rise as the sun sets.
A man of the mountain country of Minnesota, a manipulator of crowds, he is going back to the Sodom and Gomorrah that is the world. Ain't nobody there who would marry his (Jewish) sister. You're a man of the mountains, you can walk on the clouds
Manipulator of crowds, you're a dream twister.
You're going to Sodom and Gomorrah
But What do you care? Ain't nobody there would want to marry your sister.
Friend to the martyr, a friend to the woman of shame,
You look into the fiery furnace, see the rich man without any name.
A story from the age of Abraham. Cast into the fiery furnace as a boy. A man of the mountains (Hebron is the hill country). Defender of Sodom and Gomorrah -- home to his nephew, Lot. He did marry his sister (by some Rabbinic accounts) or at least passed his wife off as a sibling. Friend to God -- Hebron means friend, in Arabic it is known as al Halil, the friend (of God).
The Book of Leviticus: Here we have the troubled Jew, armed on the one hand with the Jewish Bible (Leviticus and Deuteronomy being the most legalistic books of the Pentateuch, the least meaningful for Christians unconcerned with the Commandments) and with the uncertainties and confusions of the lawless on the other hand. (These are certainly not the "only" teachers of Jesus.)

For Dylan King David (the righteous king who wrote psalms besides moonlit streams) has exemplified this intoxicating combination of the sacred and the profane. Should we be surprised? David seemed to have it all -- the bedrooms and the battles, the songs and the sacred, fame that endured for 3,000 years. Is it any surprise that as Dylan emerges from a period of Born Again renunciation he looks to David?

Like David fleeing King Saul, Dylan is still on the run, unsure of his relation to the turbulent stage on which he has been thrust, knowing -- hoping? -- that however much he wants to find peace, he will end up in bed with sin.

The book of Leviticus and Deuteronomy
The law of the jungle and the sea
Are your only teachers
In the smoke of the twilight on a milk-white steed
Michelangelo indeed could have carved out your features
Resting in the field far from turbulent space
Fast asleep 'neath the stars with a small dog licking your face
King David is in these verses. His features carved by Michelangelo, ancestor of the Messiah, prophesied to enter Jerusalem on a milk-white donkey. Sleeping under the stars while on the run from King Saul.
Who'll get there first is uncertain: Salvation is no longer guaranteed. Faith is not what it used to be. Is it up to the Jokerman to save the sick and the lame? Will he make the effort? The political world is full of strife, of violent uprisings (the Palestinian Intifada begun in 1987 was not the first time in the decade that Israel hosted nightsticks, tear gas, Molotov cocktails and rocks). And it will get worse, the apocalypse is at hand. Only a matter of time until night comes stepping in. (Or is this only a false-hearted judgement of a web spinner?) Rifleman stalking...
Shadowy world, skies are slippery gray: The world isn't fully evil, heavens aren't fully white. If, as the Tradition has it, the Messiah will come when the world is fully good or fully evil, then he isn't coming soon.

A prince today: Ok, so here the Jewish interpretation breaks down and one concedes that Dylan has been reading too much from the Book of Revelation. The prince of evil is being born; the devil is at hand. Or is it? Is the priest really the good guy? Is the harlot really the wicked woman? Isn't the Jokerman a friend to the woman of shame?

But whatever the circumstance, we come back to the Jokerman. Which path is he going to follow? Will he stop the prince? Oh, Jokerman, you don't show any response.

It's a shadowy world
Skies are slippery gray
A woman gave birth to a prince today and dressed him in scarlet
He'll put the priest in his pocket
Put the blade to the heat
Take the motherless children
And place them at the feet of the harlot
Oh, Jokerman, you know what he wants,
Oh, Jokerman, you don't show any response.

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