From The Plantation To The Penitentiary
Wynton Marsalis Lyrics


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From the Plantation
To the Penitentiary
From the yassuh boss
To the ghetto minstrelsy
In the heart of freedom
In chains
In the heart of freedom
Insane
In the heart of freedom
Insane
In the heart of freedom
In chains

From the field hand cry
To the ten to twenty-five
From the 'sold-off' men
To the raised by next-of-kin
In the cause of freedom and shame
In the cause of freedom and game

From the 'no book' rules
To the raggly public schools
From the coon and shine
To the unemployment line
In the land of freedom
In chains
In the land of freedom
Insane

From the work long days
To the dope
And drinking craze
From the stock in slaves
To the booming prison trade
In the name of freedom
Insane
In the name of freedom
And shame
In the heart of freedom
In chains




In the heart of freedom
Insane

Overall Meaning

Wynton Marsalis's song "From The Plantation To The Penitentiary" explores the issues and contradictions of freedom in the United States, particularly for African Americans. The song points out how the history of African Americans in the United States has evolved from the plantation system, where enslaved people were forced to work without pay under brutal conditions, to the current state of the prison-industrial complex, where African Americans are disproportionately incarcerated.


The lyrics of the song specifically illustrate the irony of living in a country that was founded on the principles of freedom and democracy, yet has a long and painful history of oppressing its own citizens based on race. The line "From the yassuh boss, to the ghetto minstrelsy" speaks to the ways in which African Americans have been forced to perform subservient roles for white people, whether on the plantation or in the entertainment industry. The repeated lines, "In the heart of freedom, in chains/ Insane," underscore the idea that even though slavery officially ended in the 1800s, African Americans are still not truly free, as systemic racism and discrimination remain rampant.


The second verse of the song continues to highlight the ways in which African Americans have been held back in the name of freedom, such as through subpar education and limited job opportunities. The line "From the coon and shine, to the unemployment line" points out how African American communities have historically been stereotyped and caricatured, ultimately leading to limited opportunities and poverty. The final lines of the song bring things full circle, as Marsalis points out how the legacy of slavery and oppression has led to the current state of the prison system, where millions of African Americans are incarcerated.


Overall, "From The Plantation To The Penitentiary" is a powerful commentary on the complicated nature of freedom in America, and serves as a reminder of the work that still needs to be done to truly achieve equality and justice.


Line by Line Meaning

From the Plantation
From the place where slaves worked tirelessly


To the Penitentiary
To the place where criminals are punished


From the yassuh boss
From the place where white people owned black people


To the ghetto minstrelsy
To the place where black people entertain white people in exchange for money


In the heart of freedom
In the country where freedom is supposed to be valued


In chains
But still enslaved and controlled by white people


Insane
A result of the oppression and lack of freedom felt by black people


From the field hand cry
From the pain and suffering of slaves working in the fields


To the ten to twenty-five
To the years of imprisonment for committing certain crimes


From the 'sold-off' men
From the separation of families and selling of slaves


To the raised by next-of-kin
To the responsibility of family members to take care of orphaned children


In the cause of freedom and shame
In the fight for freedom, but also feeling ashamed of the treatment received as black people


In the cause of freedom and game
In the fight for freedom, but also feeling like a pawn in a larger political game


From the 'no book' rules
From the lack of education and the inability to read or write


To the raggly public schools
To the poorly-funded, low-quality public schools available to black children


From the coon and shine
From the derogatory and demeaning entertainment performed by black people for white people


To the unemployment line
To the inability to find a job and provide for themselves and their families


In the land of freedom
In the country where freedom is supposed to be valued


In chains
But still enslaved and controlled by white people


Insane
A result of the oppression and lack of freedom felt by black people


From the work long days
From the strenuous and never-ending work done by slaves and low-paid workers


To the dope
To the illegal drug trade and addiction that plagues impoverished neighborhoods


And drinking craze
And the alcoholism that often goes hand-in-hand with poverty and desperation


From the stock in slaves
From the ownership and sale of human beings


To the booming prison trade
To the for-profit system of punishing criminals and the disproportionate number of black people in prisons


In the name of freedom
Under the guise of keeping society safe and just


Insane
A result of the oppression and lack of freedom felt by black people


In the name of freedom
Under the guise of upholding core American values


And shame
But feeling ashamed of the treatment received as black people


In the heart of freedom
In the country where freedom is supposed to be valued


In chains
But still enslaved and controlled by white people


Insane
A result of the oppression and lack of freedom felt by black people




Contributed by Zachary L. Suggest a correction in the comments below.
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