When in the course of human events,
(Jefferson is referencing the famous Declaration of Independence—for which he was the primary author—which says, "When in the Course of human events, it becomes necessary for one people to dissolve the political bands which have connected them with another…")
It becomes necessary for a battle to commence,
(Continuing the quote started in the previous line, Jefferson states that it has become necessary at this point to engage in a rap battle against Douglass.)
Then kplow! I hit 'em with the illness of my quill!
(Jefferson will strike down any enemy with the power of words and writing just as he did to the British Empire.)
I'm endowed with certain unalienable skills!
(Jefferson also says he has rapping skills that cannot be taken away, again referencing the Declaration: "[All men] are endowed by their Creator with certain unalienable Rights, [and] among these are Life, Liberty, and the pursuit of Happiness.)
Let me run down my résumé, will ya?
(He offers to state his metaphorical "résumé" of lifetime accomplishments, continued in the next line.)
Set up a little place called the United States; sound familiar?
(Jefferson had been instrumental in founding the United States of America, a country whose customs should be familiar to Douglass as he is a citizen thereof.)
I told King George he could eat a fat dick!
(Jefferson was the writer of the Declaration of Independence, which was in a sense a way of telling King George III—the British monarch who was the object of the declaration's Grievances—of the contempt Americans had for him.)
When it comes to declarations, I'm the first draft pick!
(Jefferson was his fellow Founding Fathers' "first pick" for the man who would help write the "first draft" of the Declaration. This is also a sports pun, as the "first draft pick" is the athlete held in the highest regard for his/her on-field ability, thus the first to be selected by a sports club that would want him/her.)
I'll topple any tyrant, so kings and pirates beware!
(Being the main author and signatory of the Declaration of Independence, Jefferson could be said to have ended the tyrannical rule of King George III. While president, Jefferson also engaged in a war with the Barbary Pirates in North Africa over attacks on American merchant vessels.)
I'm so down with revolutions, I invented the swivel chair!
("Revolution" can mean to turn against a higher power, as well as for one object to move around another. In this sense, however, the word "revolution" is being used synonymously with "rotation", which is how a swivel chair functions. Jefferson invented the first swivel chair, displaying his involvement in both kinds of revolutions.)
(Oh!) I've many volumes on my shelves, it's true,
(Jefferson was interested in linguistics and literature, owning many books. The catch to this is explained in the next line.)
But I've yet to read the three books you wrote about YOU!
(The three books Douglass wrote were all autobiographies. Despite reading a lot of books, Jefferson does not want to read Douglass' works, criticizing how he only writes about himself.)
Looking like a skunk in a three-piece suit,
(Jefferson calls Douglass a skunk, referring to his black hair with a white stripe down the middle. Jefferson contrasts Douglass' unkempt appearance with the formal suit he wears.)
Didn't come back from Paris to battle Pepé Le Pew!
(Alluding to his previous line, Jefferson directly compares Douglass to Pepé Le Pew, a French skunk character from Looney Tunes. After the Revolutionary War, Jefferson became a Minister in France before returning to the United States, where his political career would take off. Jefferson tells Douglass that he came back from France to do more important things than battle a person who looks like the French cartoon character.)
First Secretary of State, VP number two!
(Jefferson explains why he has no time to battle Douglass by listing his political careers: he was the first Secretary of State and the Vice President to second President John Adams. The order of him being in those positions also counts upward.)
Not to mention third President; the fuck'd you do?
(Jefferson finishes his upwards count by saying that he was the third President of the United States. He then asks Douglass what he accomplished, knowing that Douglass' achievements could not compare to his.)
You finished? …Okay.
(Douglass is mockingly asking Jefferson if he is finished so he can take a jab at him.)
Straight outta bondage! A brainy mother fucker here to diss you!
(Douglass begins his verse, referring to his success of escaping from slavery. This line is a direct reference to N.W.A.'s "Straight Outta Compton", where Ice Cube begins his verse on the song nearly the same way; "Straight outta Compton, crazy mother fucker named Ice Cube!" The film based on the group shows how they rapped about their brutal lives in Los Angeles, so Douglass talks about how he escaped from slavery to speak his opinion in the same manner that N.W.A. did. Douglass was widely regarded as incredibly intelligent, so he says he will use his brainpower to beat Jefferson.)
Big hair, big nuts, big issues!
(Douglass references the large volume of hair on his head before declaring that he has large testicles, which indicate a courageous man. He tells Jefferson that, like those, the issues he is bringing forward are large and important.)
Starting with your nickel: there's a real declaration!
(Douglass references Jefferson being on the front of the American nickel, and states that he will make a declaration, a reference to Jefferson writing the Declaration of Independence. By calling his declaration a real one, Douglass discredits the importance of the Declaration of Independence.)
Heads for racist, tails for slave plantation!
(Douglass refers to the pictures on the front (heads) and back (tails) of the nickel. On the front is Jefferson, who Douglass calls a racist due to owning slaves, and on the back is Monticello, Jefferson's home, where his slaves worked to farm crops on his plantation.)
You're a soft white Monticello Marshmallow!
(Douglass mocks Jefferson's pale skin by comparing him to a marshmallow, and alludes to Jefferson's home Monticello once again.)
Watching my people sweat while you sat playing cello! Hello!
(Jefferson played the violin and cello throughout his life. Douglass criticizes him for doing such a frivolous activity while his African slaves worked the fields like Douglass did, sweating from the temperature and the large amount of work.)
But now you're facing me, Freddy D!
(Douglass tells Jefferson that he is battling someone much like his slaves, referring to himself as "Freddy", a nickname for Frederick, and only using his last initial, creating a more stylish and "street" tone around him.)
I'd never work for your ass, but I'll kick it for free!
(Douglass says that he would never work for Jefferson like his slaves did, but he would kick his ass, or beat him, for free, referencing how slaves carried out unpaid labor.)
(Ugh!) Your stone face on Rushmore ain't nothing!
(Douglass says that the stone carving of Jefferson on Mount Rushmore, a famous monument, is nothing in comparison to Douglass' expression.)
Check my photos: now, that's real muggin'!
(Douglass was the most photographed person of his time period, in an effort to give a more accurate depiction of black people. Douglass says that the photographs of his head, also known as mugshots, are better than the carving of Jefferson's head. "Muggin'", meaning to extensively study, could also refer to Douglass' learnedness.)
The face of a free man, taught himself to read, man!
(Douglass gained freedom from being a slave, and while he was a slave he taught himself to read, both of which were extremely uncommon for slaves to do.)
No compromise; you couldn't whip a 5th of me, man!
(The Three-Fifths Compromise was a device used in the apportionment of Congressional representation, whereby each five slaves that a person owned would count as three free persons in order that a proper number of Representatives was sent from each state, which Douglass uses to declare himself free from the whippings Jefferson would give to his own slaves without any compromise. This is also a way of saying that Jefferson could never own Douglass, whether as a slave or in a rap battle, and not even a part of Douglass could be whipped by him.)
You got a self-evident truth of your own:
(Douglass references the Declaration of Independence and Jefferson's statement in it about self-evident truths when it comes to nations such as equality of men. Douglass says that Jefferson has an aspect of himself that everyone can see.)
You let freedom ring, but never picked up the phone!
(The song "My Country 'Tis of Thee", a spin on Britain's "God Save the King", is an American anthem about freedom written years before the emancipation of slavery in America. The song features a lyric stating, "Let freedom ring." Douglass compares this ringing to that of a telephone, which rings to alert someone of an incoming call. Douglass implies that by "letting freedom ring", Jefferson chose to ignore freedom's call, as Jefferson never gave all men freedom.)
Aw, Frederick, I've never heard a verse I dug less.
(Jefferson makes a pun on Frederick's last name, using the homophone "dug less". He claims he was not impressed by his opponent's first verse.)
Alright, I admit it. I confess!
(Jefferson is ready to admit his mistakes with regards to the slave trade.)
I participated in a broken system that I hated,
(Jefferson was in fact not particularly fond of the slave trade system despite taking advantage of it.)
But I needed to keep my financial status situated!
(Jefferson explains that the only reason he participated in slave trade was to maintain financial stability by being able to produce mass amounts of crops at low cost. This was useful to him as he spent a lot of his life in debt.)
And the words I used were "hideous blot"
(Jefferson referred to slavery as being a "moral depravity" and "hideous blot" in a letter to William Short in 1823, and campaigned extensively for its abolition.)
To describe the slave trade and the pain it hath brought!
(Continuing from the previous line, Jefferson shows that he knew of the horrendous acts that occurred in the process of the slave trade, and this was a core reason that he felt it should be abolished.)
And I fought to stop the trade of new slaves in Virginia
(In 1779 and 1780, Jefferson served two one-year terms as Governor of Virginia, during which he attempted to prevent any more slaves being sold in the state, but to little avail.)
When I ran the whole state and still made it home for dinner!
(Jefferson alludes to the very short terms he served as Virginia's governor, attempting to convey that he did not have very long to campaign against the slave trade. He implies that, had he more time, he might have been able to stop it sooner than it wound up being ended.)
So forgive me; I was busy, man. I had a lot to do,
(Holding so many high positions of power in his lifetime, Jefferson was often dealing with many issues, both national and regional, at once. Due to this, he says he was unable to act faster than he would have liked to prevent the slave trade. He asks Douglass' forgiveness on this matter.)
But we did it. You're free now, so…we cool?
(Jefferson is trying to apologize to Douglass for how long the actual abolition of the slave trade took, but because it was eventually stopped, he offers a fist bump, a stereotypical African-American gesture of respect.)
This ain't Louisiana, man. I ain't buying it!
(As reference to the Louisiana Purchase, a deal made with France during Jefferson's presidency where America purchased a large amount of land, Douglass says that he's not "buying" Jefferson's apology and is still skeptical. This might also be owing to Jefferson's attempt to appear and talk more colloquially to appeal to his opponent, which Douglass finds patronizing.)
You talk about freedom, but you ain't applying shit!
(Douglass shows his discontent with Jefferson's claims of freedom, as he wrote in the Declaration of Independence that "all men are created equal", with no changes to African-American rights. He also refers to how Jefferson spoke out against the slave trade yet took a very long time to apply any appropriate laws.)
So no, we ain't cool, you founding absentee father!
(Though caring for his white children, Jefferson was known to have multiple affairs with one of his slaves, which resulted in Jefferson's mixed children, but he chose to ignore them despite still holding them as family. Douglass correlates this to Jefferson's role as a founding father of the United States.)
Man, you had six babies with your slave mama and never even bothered
(Jefferson had six mixed children with his slave, Sally Hemings, and only four of them survived. Douglass brings this up to make a point in the next line.)
To free her when you died on the 4th of July!
(While touring Paris with Jefferson, Sally had the option to be a free person and remain in France or return to America as Jefferson's slave. After getting pregnant from him, she chose to go with him as his slave as long as her children would become free when they reach 21, which he had not done so until his death in 1826. While he loved his African-American mistress and their children, she was never freed by him, so Douglass uses this fact as a point of hypocrisy in his lifestyle. Jefferson famously died on July 4th, Independence Day for America.)
It's a very important holiday, but what the fuck does it mean to this guy?
(Douglass states that the Fourth of July—the day on which the Declaration of the United States was and is celebrated—is nothing more than a mere day to Jefferson; it had less significance to him than a day he describes in the following line. This also refers to Douglass' speech, "What, to a slave, is the Fourth of July?", where he questions the relevance of a celebration of freedom to a still-constrained slave.)
'Cause I celebrate December 6th, 1865:
(Douglass states that instead of celebrating the Fourth of July, like most Americans (black, white, or any other ethnicity), he instead chooses this date for a reason he mentions in his next line.)
The day the 13th damn amendment was ratified!
(The 13th Amendment to the Constitution ended slavery in the United States ("Neither slavery nor involuntary servitude, except as a punishment for crime whereof the party shall have been duly convicted, shall exist within the United States, or any pace subject to their jurisdiction"). Naturally, this makes an adamant abolitionist such as Douglass happy, and even more happy when it was ratified, or passed).)
And I ceased to be an alien to your unalienable rights,
(Douglass states that Jefferson's unalienable rights—Life, Liberty, and the Pursuit of Happiness—were never given to anyone of color before the 13th amendment, so he proclaimed himself to be an "alien", someone whose residential status is that of a foreign country.)
And we the people stopped meaning we the people who are white!
("We the People" are the starting words of the Constitution of the United States, a document in which many laws and rights are recorded as the country's foundation. Initially, the terms of the Constitution were interpreted as applying to white male citizens of status, ignoring all others. Douglass takes the starting words of this document and claims that the words now apply to all citizens regardless of color, gender, or social status.)
Man, you did some good things; I ain't denying your fame.
(Douglass settles down a little, acknowledging that Jefferson's fame is somewhat well-deserved, and that during his political career he campaigned for and passed laws on many good causes.)
I'm just saying they need to put an asterisk next to your name.
(Douglass states that Jefferson isn't all he's made out to be, essentially creating a perfect character behind an imperfect man. An asterisk next to a piece of text denotes a side point relating to said text. In saying Jefferson needs an asterisk next to his name, he is claiming that while Jefferson performed many good deeds, he still took part in the slave trade and failed to get the trade abolished as early as he could have. This is based on a comedy routine by Daniel Tosh in which he relates the addition of an asterisk in place of baseball player Barry Bonds's name on a baseball card (done as a callback to his 756th home run baseball being branded with an asterisk by a buyer at an auction as retaliation for his use of steroids in play) to the hypothetical idea of placing an asterisk next to Babe Ruth's name for his "[setting of] records before black men could compete" in the sport, which segues into a joke about the founding fathers' racism and the "implied meaning" to the phrase "all men are created equal" in the Declaration of Independence.)