This show was made by the same people who gave us Tiny Toon Adventures and Animaniacs, so it should come as no surprise that it got away with its share of inappropriate jokes and references.
One notable Running Gag, in fact, was to have the network censor Lydia Karaoke complain whenever the show makes jokes and references that would seem inappropriate on a children's show, only to be abused, ignored, and/or ultimately defied.
- "The Wild West"
- A reference to breastfeeding is made when a cow mentions that cows made it big while a Big Fat Baby is drinking from a bottle. After the Big Fat Baby finishes, she looks at the cow's udders in curiosity.
- Shortly after Billy the Kid is turned into a girl (after Lydia Karaoke objects to Billy telling the kids to get the gun from the shed to help him escape and announcing that she's changing him into a girl to get more female viewers), she tears at her blouse and starts exposing her shoulders. Because this is still a children's show, Billy subsequently becomes male again by unzipping his female self like a latex suit.
- "The Renaissance"
- Catherine the Great makes an appearance and a horse replies to a statement about her by remarking "I'll say", referencing a famous tall tale that Catherine the Great died while trying to have sex with a horse.
- Lydia Karaoke and Sister Windbag eventually get into an argument and fight over depicting nude paintings on TV.
- "A Blast from the Past"
- During the "This Was Your Life" segment, one of the people from his life that King Tutahnkamen is reunited with is his wet nurse, who is portrayed by the World's Oldest Woman. Not only does Noah Webster appear to explain what a wet nurse isnote , but King Tut's wet nurse tries to invite him and his older brother Smenkhkare to resume breastfeeding from her.
- It is mentioned that King Tut and his wife married when they were nine and eight respectively. Miss Information quickly points out that this is illegal in most states.
- When it is asked what a vestal virgin is, Lydia Karaoke objects to the word being mentioned. The World's Oldest Woman answers with "Let's just say we didn't do a lot of dating and leave it at that".
- The "wet nurse" joke happens again when they go over the she-wolf looking after and nursing Romulus and Remus, who aren't shown onscreen when they nurse unlike the she-wolf's own cubs.
- "Tribute to Tyrants"
- The World's Oldest Woman portrays Lady Godiva, and that includes acting out the legend that she rode horseback in the nude to protest her husband Leofric.
- Later, the World's Oldest Woman portrays Cleopatra and in two separate scenes is in the bath while making a suggestive comment toward Caesar and Mark Antony.
- When the narrator mentions that Cleopatra is believed to have died from being bitten by an asp, he is told to watch his mouth because it's a family show.
- "Great Heroes of France" features a reference to the notorious rape scene from Deliverance where Lewis and Clark encounter a pair of creepy-looking hicks who tell Lewis that they'll make him oink like a pig.
- The "Great Women in History" segment of "When Time Collides" contains some incest jokes. Cleopatra mentions marrying two of her brothers and Joan of Arc assumes that Martha Washington being married to the Father of Our Country is the same as being married to one's father.
- General Sherman gets away with saying "War is hell" in "General Sherman's Campsite" (but not before Lydia Karaoke objects and offers substitutes like "War is a big no-no" or "War is that horrible place downstairs").
- At the end of the World's Oldest Woman's theme song in "Inventors Hall of Fame - Part II", she makes this interesting remark.World's Oldest Woman: I dated the Missing Link, and let me tell you, you weren't missing much.
- In "More Explorers", when Eric the Red asks to be pinched to prove he isn't dead, he gestures toward his behind and the World's Oldest Woman appears to be a little too interested in pinching him.
- Julius Caesar mentions that Athena/Minerva "has a nice curve-a" during the "What's in a God's Name?" musical number in "Loud Kiddington's Ancient History".
- In "Super Writers", Edgar Allan Poe states that "The Cat in the Hat has been spayed" as one example of how he, Sappho, and Basho have rewritten many famous works of literature.
- In "World War II", Franklin Delano Roosevelt's dog Fala remarks "Let's bite'em in the assets!"
- In "Histeria Around the World II" has Joan of Arc ask who is ready to bare themselves. Before she clarifies that she meant for the other members of the support group to bare their souls, the World's Oldest Woman volunteers on the grounds that it is getting too hot and starts to take off her shirt.
- Any gag involving Mr. Smartypants, a fellow who hides in his own trousers, and Lydia Karaoke, including one hilarious scene called "What's In My Pants" which takes advantage of Trouser Space to have Mr. Smartypants reveal increasingly Freudian objects, much to the dismay of Lydia, who has just about given up by the time he pulls a model of the Eiffel Tower out of his pants.
