SNL beat 'em to that joke, with De Niro as Thomas Jefferson. (Followed by a quick “I think I could love you, Sally Hemings,” prompting a “You’re the boss.”)
“You have a great voice. Really, a great voice. Have you ever thought about being a singer?”
“Um, it’s really not an option for me.”
The deservedly ill-received The Secret Diary of Desmond Pfeiffer was a 1998 UPN TV series that was protested by the NAACP because it made light of slavery. It was set during Lincoln’s administration, and only four episodes ran before the combination of outrage and low ratings shut it down.
There’s also the Futurama episode where Bender becomes a space-pharaoh. And a famous Simpson’s Hallowe’en episode: “Don’t blame me – I voted for Kodos!”
When does Song of the South take place? I’m not sure if Uncle Remus was a slave in the movie or not. (The men Joel Chandler Harris based him on were definitely slaves.)
Saturday Night Live has done several sketches about slavery, including a multisexual parody of Mandingo with the original Not Ready for Primetime Players and a Thomas Jefferson-Sally Hemings sketch with Robert Deniro & Maya Rudolph that made fun of Deniro’s own well known appreciation for beautiful black women.
from Wiki:
The setting of the film is the deep South of the Reconstruction era. Harris’ original Uncle Remus stories were all set **after **the American Civil War and the abolition of slavery (Harris himself, born in 1845, was a racial reconciliation activist writer and journalist of the Reconstruction era). The film makes several indirect references to the Reconstruction era: clothing is in the newer late-Victorian style; Uncle Remus is free to leave the plantation at will; black field hands are sharecroppers, etc."
<Bender>You call that motivating me?</Bender>
So, what, you’re saying I’m on your ignore list? 
There’s also one where the founding fathers use Ben Franklin’s time machine to visit the present day: promptly coming up with quick and practical solutions to our budget problems, only to get derailed by reporters asking about owning slaves and having sex with slaves and what their wives thought about all the sex with slaves, finally prompting an exasperated Thomas Jefferson to clarify: “I just want to remind you all that we’re talking about the eighteenth century. And yes, most landowners in Virginia had slaves. And yes, it was common for a master to take as his mistress a negro wench. I think I said the wrong thing.”
George Washington then steps in: “We do have a very important deficit reduction package to talk about; is there any way we can get off this slave sex issue?”
Other little-known comedies set in Roman times include Chelmsford 123 (deservedly forgotten), which was set in Roman Britain, though I don’t think it included any actual slaves. And just this year was the British sitcom Plebs, which features a slave as one of the main characters.
As Prof. Pepperwinkle says, Uncle Remus was a former slave in the book. He is, however, very devoted to the family of his former masters and lives on the plantation. His is disdainful of many of the freedmen he sees in town.
You are correct, however, that Harris collected his tales mostly from slaves before Abolition.
Can’t remember if Wholly Moses had slaves or not
In the sci-fi spoof Ice Pirates, the protagonists are captured by a company that sells eunuch slaves, apparently at such a high volume that they castrate them by assembly line. Thanks to the timely intervention of an ally, our heroes are able to remain intact, but still have to pose as slaves in the show room before they can escape.
Are we only doing movies? If books count, Terry Pratchett’s Small Gods involves the invasion of classical Greek expy Ephebe by the brutal theocracy of Omnia. The Omnians expected the slaves to rise up and help overthrow their masters, but instead they turn on the invaders, correctly realizing that they have more freedom as Ephebian slaves than they would as Omnian citizens.
“We commend the body of Hermenthotip to the abode of the damned. The damned good looking!”
::grins::
“Pharaoh commanded me to tell that joke at his funeral.”
I’m quite irritated I can’t find a video clip of that scene. I’d even settle for a screencap of that grin on his face after he delivers the punch line.
I didn’t mention Chelmsford 123 because, like you, I couldn’t recall any slaves in it. And Plebs is so awful I couldn’t bring myself to mention it!
Well, if we’re counting books there is Asterix and the Laurel Wreath, in which Asterix and Obelix sell themselves into slavery in a Roman household and set about accidentally ruining the place and the institution of slavery in their quest for the titular wreath, and The Mansions of the Gods, in which they encounter Roman slaves building an apartment block in the forest outside their village. Both brilliantly funny - the slave auction in Laurel Wreath is one of the funniest scenes in the whole series - and for all the comedy, actually quite accurate about how Roman slavery worked.
Key & Peele were hilarious as slaves on the auction block who give their running commentary each time someone else gets sold ahead of them.
“Okay, well, you have to buy that dude.”
“I mean, that guy’s huge.”
“A massive individual.”
“That’s two of me.”
"Anybody would buy him.
“I’d buy that dude.”
“My question is, how’d they catch him?”
From Your Highness:
“You fought with honor, why don’t you treat yourself and take rest at our castle?
We have all the slaves, pickles and servants one could ever desire. We have dancing bears, orientals and all the berries care to pick.”
It’s certainly what I thought of. While not 100% comedy, it has some seriously comedic sections.
[QUOTE=Terry Pratchett]
“Slave is an Ephebian word. In Om we have no word for slave,” said Vorbis. “So I understand,” said the Tyrant. “I imagine that fish have no word for water.”
[/QUOTE]
And there is a little-known American book called The Adventures of Huckleberry Finn. It has been turned into a movie, more than once. It is funny.
The comic musical 1776 discusses slavery at some length, including a very serious song about it: 1776 and Slavery - YouTube
The Three Stooges Meet Hercules