Assigned a family tree project, Lisa discovers that all of her ancestors were horrible, except, from an attic find, a little girl named Eliza Simpson. In 1860, she assisted a runaway slave named Virgil (who looks like Homer if he was black, or Cleveland Brown if he were drawn Simpsons-style). She is relieved until Milhouse also finds a diary from his ancestors, who have a different take on how Virgil was treated by the Simpson family.
Tropes:
- Artistic License – History:
- Mabel says that she is taking Virgil to Canada. The story is set in 1860, 2 years before Canada was named.
- The flag shown is the modern Canadian flag, which was first established in 1965, over a century after when the story is set.
- Awful Wedded Life: Judging by her expression in the wedding photo in the old film Lisa watches, Eliza was not all that happy to marry Milhouse's ancestor.
- Bait-and-Switch:
- Before the commercial break, Lisa reads from Eliza's diary who's excited to get her first slave. It then reads that she's excited to her first slave to freedom.
- In Eliza's story.Eliza: Follow me north to freedom.Virgil: I don't think so.Eliza: Why, because I'm young and I'm a woman?Virgil: No, because you're pointing south.
- We're lead to believe that Hiram Simpson is Homer's ancestor and analogue in the past: he looks like him, acts like him and is bribed into helping Virgil with "wheel cakes"—that is, the ancestor of Homer's Trademark Favorite Food. The story gradually reveals that Virgil, not Hiram, is Homer's ancestor, as Hiram's wife Mabel divorced him and married Virgil, who then took her former married name because he had no surname of his own. In other words, Homer descended from the inventor of the donut, not just an early adopter. Virgil's resemblance to Homer isn't obvious until he's seen later in life with a bald head.
- Bittersweet Ending: Eliza was left behind by her mother with her father and lived the rest of her life regretting her act of cowardice, but Mabel and Virgil did manage to escape to Canada, Lisa finds out that she does have noble ancestors and might not even be related to many of the horrible ones.
- Bread, Eggs, Milk, Squick: Each of the Simpsons (minus Marge) reflect on how their black ancestry is shown in their lives.Bart: So that's why I'm so cool!
Lisa: And that's why my jazz is so smooth!
Homer: And that's why I earn less then my white co-workers! - Break the Cutie: Milhouse humiliates Lisa in front of the entire school by pointing out the single decent ancestor she has allowed a slave to be recaptured.
- Broken Pedestal: Lisa was thrilled to learn that her ancestor, Eliza Simpson, was part of the underground railroad and helped a black slave to freedom, only to be severely disappointed to learn that Eliza was a coward who did not stand up to Col. Burns when he came to reclaim his slave.
- The Chase: Eliza and Virgil run their way through a dark forest while being hunted by racist patrollers.
- Comically Small Bribe: Deconstructed. Hiram sells out Virgil to Col. Burns in exchange for a random prize, which is a pair of new shoes. As a result of this poor showing of moral character, his wife Mabel leaves him to help Virgil escape for good, and when Virgil and Mabel get married, he has to give up one of his shoes to them, which is clearly a blow to him since he pettily keeps the laces and the last family photo of him shows him disgruntled and miserable. Appropriately, his actions cost him much more than they earned him, and even a part of his miniscule bribe.
- Continuity Cavalcade: Lisa's trip through the family attic features a treasure trove of trinkets and memorabilia featured throughout the series.
- Cordon Bleugh Chef: Mabel was able to create a variety of recipes using unpleasant animal parts as the main ingredients. Apparently they were popular enough to make a cookbook out of them.
- Crazy-Prepared: Bart carries a map of the school with target locations to blow up in the event he came across explosives.
- Dramatically Missing the Point: After Eliza's first diary entry gave the idea that she and the family were slaveowners, Homer expresses delight in the idea of the Simpsons being in management for once.
- Everyone Has Standards: Milford Van Houten (Milhouse's ancestor) was so disgusted at Eliza for not standing up to Col. Burns that he didn't want to look at her again. Though it's shown in Eliza's video interview that they did get married as adults.
- Exact Words: After witnessing Eliza Simpson backing off when her father told Col. Burns where Virgil was hidden, Milford Van Houten said he couldn't look her in the eye again. The next day, he lost his sight after drinking tainted well water. A video of Eliza in old age shows that she married Milford.
- Food as Bribe: Virgil manages to win Hiram's favor by making his special wheel cakes.
- Freeze-Frame Bonus: During Eliza's interview, her ragdoll is with her only now she's as miserable as her owner.
- I Gave My Word: Hiram Simpson told about his oath to make Col. Burns stop trying to beat Virgil's whereabouts out of him. Col. Burns then decided to bribe Hiram.
- Generation Xerox: Mr. Burns looks like Col. Burns used to during Virgil's tale, and the Simpson ancestors are depicted as looking exactly like their modern-day counterparts, albeit with different hairstyles. (Mabel even looks exactly like Marge, despite being Homer's ancestor, not Marge's. Perhaps the Simpson men all have a type.)
- Gilligan Cut: Lisa expresses eagerness in learning about all the noble and wonderous ancestors that are part of the Simpson Family Tree. It then cuts to her finding nothing but crooks, criminals, creeps and curs.
- Hiding Your Heritage: Grandpa mentions that he didn't mention that his great-grandfather was black because of the racist environment he grew up in.
- Improbable Age: Mr. Burns reacts to mentions of the Civil War-era Col. Burns with "I haven't heard my father's name in years."
- Jerkass Has a Point: Homer takes the diary from Lisa to stop her from reading about her one good ancestor, saying that if she keeps reading, she'll only be disappointed, and he's right. Lisa learned that the one ancestor she thought was a good person turned out to be a coward.
- Kid Has a Point: Bart snarks that the Underground Railroad, not being underground or a railroad, should have been called "the Aboveground Normalroad." Homer, Marge and Lisa all admit that this makes more sense.
- Mistaken for Clown: Invoked. Thanks to a crusty old clown, Virgil was able to disguise himself as a payaso to throw off the racist horsemen.
- Noodle Incident: Grampa is implied to have spilled secrets about the D-Day landings to the Germans during the war.
- Pet the Dog: While the librarian at the Springfield Library is initially dismissive toward Lisa when she tries to prove that Eliza wasn't a coward, her tune changes when she starts crying and gives Lisa the key to the film vault to get her answers.
- Same Surname Means Related: Colonel Burns mentions that his story will one day be told by his descendants, Ric and Ken Burns.
- Sarcastic Clapping: Milhouse does this after hearing Lisa's over-glorified retelling of her ancestor.
- Seen It All: After Eliza sheepishly admits that it's her first time helping a slave escape, Virgil admits that he's made fourteen attempts.
- Series Continuity Error:
- The Simpsons didn't arrive in America until the early 1900s when Abe was a child, as seen in "Much Apu About Nothing" (although Abe's ancestors are shown living in Canada at the end of the episode, not the U.S.). Granted, Abe's stories aren't the most reliable of sources.
- Lisa should have known that not everyone on Homer's side of the family is an idiot, a criminal, a freak, a sexual deviant, or a failure, as seen in "Lisa the Simpson", when she learns that all the women on Homer's side of the family (save for Homer's half-brother, Herb, who, despite going broke twice, was a fairly successful businessman) are smart, emotionally mature, and are in high-paying, respectable careers. And why didn't she think to look into Marge's side of the family for good family members, or Mona's side of the family before she married Abe?
- Virgil's story conflicts with the Simpson family tree
◊ from The Simpsons Uncensored Family Album 19 years earlier. Specifically, Abe is said to be named after his great-grandfather; by extension, that makes Virgil his great-great-grandfather. However, in the family tree, their respective branches are occupied by Howland and Garwood Simpson, respectively. It is left unclear whether or not Abe's story is reliable, if the earlier book was retconned, or if Abe tampered with the family tree to avoid racist remarks that might have been made if Virgil's picture remained.
- This Is the Part Where...: After blowing up a school stump, Bart tells Willie about the "My Kea!" part of the explosion. Cue the stump falling on Skinner's Kea car.
- Took a Level in Jerkass: Milhouse, of all the Springfieldians, tells his ancestors' version of the story with the only intent of humiliating his crush, which is reminiscent of what he did to her several seasons earlier in "Little Girl in the Big Ten". And just like there, he never gets called out or gets any comeuppance for this or even apologizes to Lisa at any point.
- Underground Railroad: Or, as Bart believes it should be called, "Aboveground Normalroad".
