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Robin Hood: Men in Tights. Laser-guided arrow? Those were bleeding-edge and rare. The one shown in the film came all the way from Jersey. And the castle with the car alarm on the portcullis, the Theme Tune Rap in 12th century England, the glowing neon exit sign over the archway in the castle, and the Sherriff of Rottingham resorting to a pneumatic jackhammer to get through Marian's chastity belt. Atchoo's pumps are a case of Throw It In, as Dave Chappelle was wearing them on the set and Mel Brooks just had to throw in a joke about them. Then there's the castle repo men, the Braille Playboy that Blinkin is reading (and Blinkin's sunglasses), and the empty fruit tin cans used as heads on the training dummies.
Blazing Saddles is an even better example, as there are anachronisms in nearly every single scene (which is even more odd considering the period-appropriate racism was the basis of the plot), and ends with the characters in a modern theatre watching the end of the film.
History of the World Part I is filled with them, like every other Mel Brooks movie in a historical period. Characters travel from Ancient Rome to the Holy Land of the same general period...on El Al (ship line). One of the Roman-period characters turns up in Revolutionary France. A dinosaur eats a caveman. The list goes on.
Muppet Treasure Island has a bit of this - most of it with the rat tourists on Rizzo's cruise, but Piggy claims she got her necklace from "the shopping channel". But then, this is the Muppets we're talking about; if logic and humor ever came to a head here, odds are the latter usually prevails.
A Knight's Tale goes mad with this to great effect, dropping any pretense of historical accuracy and just doing whatever was the most awesome. It begins with the crowd at a joust singing and stamping their feet to "We Will Rock You" by Queen. The director explained this as a way to help the audience relate and convey the people felt the same way about their music and dancing that modern people do. It's an extension of the Translation Convention. On the other hand, professional historians have noted the impressive accuracy in regards to etiquette, costumes, speech and such, which gave the impression that the filmmakers could have made a perfectly accurate movie about a knight rising from the working class; instead, they chose to make an awesome movie with piles of anachronisms, that was also more fun. This is a film in which 14th century London has a wooden version of the London Eye.
Much like A Knight's Tale, Moulin Rouge! also invokes this frequently, deliberately, and effectively, with characters in fin-de-siècle France singing everything from "The Sound of Music" to Nirvana.
Disney's The Emperors New Groove is another example of taking the "bones" of a historical milieu, in this case the ancient Inca empire of South America, and hanging a lot anachronistic (and very funny) jokes off them.
The sudden presence of a floor buffer was particularly confusing. But then, it was so very Disney.
In the category of "particularly confusing," the people in the diner singing "Happy happy birthday" to Yzma. And the existence of the diner itself...
Monty Python admitted that the armour (and clothing in general) in Monty Python and the Holy Grail was anachronistic; it was more 13th century than Dark Ages. Also, a French garrison in the middle of England, the fact that England supposedly had one singular king at all at that point (although considering none of the peasants know about having a king, it's possible Arthur is simply making a claim to kingship), the construction of a giant wooden rabbit, and the historian and the police cars makes for a pretty anachronistic (and hilarious) movie.
Not forgetting the aforementioned peasants not only fail to recognise Arthur's claim to kingship, they're part of an anarcho-syndicalist commune and ridicule his claims as the oppression of the working classes.
More likely ignorance or "didn't care" than deliberate humor is the ending in which the heroine emigrates to a fully established "Virginia Colony" at least a decade before the first permanent settlement, Jamestown, was even founded.
Stephan Elliott's adaptation of Easy Virtue is set in the 1930s and includes songs such as "Sex Bomb" and "When the Going Gets Tough, the Tough Get Going".
Casino Royale (1967) stars David Niven as the original James Bond, whose name and number were appropriated after his retirement for morale purposes. It's mentioned he'd been awarded the Victoria Cross at Mafeking, a siege that took place in 1899-1900. Niven is in his late 50s here, but this would date Bond as around 85 at least. Bond had an illegitimate daughter by Mata Hari, who was executed in 1917. The daughter is played by a 25-year old Joanna Pettet, but she would have to be 50 at least. But then, this movie is not at all logical or linear.
In Who Framed Roger Rabbit, the Singing Sword sings "Witchcraft," which was written in 1953. The sword itself is based on a similar sword from the 1958 Looney Tunes cartoon "Knighty Knight Bugs". The movie takes place in 1947. Also, Road Runner and Wile E. Coyote appear in the film despite debuting in 1949.
In regards to cartoon characters that debuted after 1947 appearing in the film, the filmmakers handwave it as them "not having made it in films yet".
In The Princess And The Pirate (1944), Bob Hope is a walking anachronism, being his fast-talking, wisecracking 20th century persona in the middle of a swashbuckling pirate movie.
Woody Allen, who has stated his appreciation of Hope, played some period roles the same way, as in Love And Death, and the segment of Everything You Always Wanted To Know About Sex, where his medieval court jester is trying to seduce the queen - he quips "I must hurry because soon it will be the Renaissance, and before you know it we'll all be painting!"
Your Highness, a fantasy comedy set in medieval times and starring Natalie Portman, James Franco, Zooey Deschanel, Danny McBride, and Justin Theroux, aims for just this. The f-bomb gets dropped several times throughout the red-band trailer, including a use of the word "buttf**k". Natalie Portman also wears a modern-looking getup of a bikini top and thong when she bathes in the river. McBride's character, Thadeous, tells his brother, "handle your shit Fabious, please."
Using the F-word isn't as much of a problem as you might think. The exact origin of the word is a bit unclear but could have existed in the later parts of medieval times.
Machine guns did exist back then. They were brand new tech, gigantic, and had to be moved around on carts because of their weight, but they did exist.
Kung Pow! Enter the Fist does this intentionally and constantly, such as Betty using a cigarette lighter, or a medieval Chinese town having a Hooters, a Taco Bell, a Radio Shack, and a place that sells A LOTTA nuts, and also apparently french fries. It is one of the saner things in a film that delights in taking Refuge in Audacity though, so they are often barely noticeable.
At the end of Scrooge, during the reprise of "Thank You Very Much", Scrooge dons a red Santa Claus suit. This version of Father Christmas/Santa is American and didn't appear in Britain until much later (this version of the story is set in 1860, according to the Ghost of Christmas Present)
The song "I've Got a Dream" from Tangled involved one of the Snuggly Duckling thugs playing a piano despite the film taking place in the Middle Ages, as well as Rapunzel playing an acoustic guitar and a brief appearance of a mechanical clock during the song "When Will My Life Begin?".
Actually, according to Word of God the movie takes place in the 1780s.
Similarly, the song "A Guy Like You" from the earlier animated Disney film The Hunchback of Notre Dame also featured a piano in the Middle Ages.
Also, poledancing during the "Topsy-Turvy" number.
Disney's Aladdin toys with this during "A Whole New World", where classic era Roman columns are spied by Jasmine and Aladdin. Not in ruins, either. Someone at Disney must have taken it literally, because the Disney TV series had a crossover episode with Hercules. For those playing at home: Muslim Arabia=AD, Ancient Greece=BC.
There's also the Sphinx being chiselled out of stone. Estimates of its age cover a huge range, but it's definitely much older than Islam. Several millenia at least. Maybe even as much as 10,000 years.
"Al, you're not gonna find another girl like her in a million years. Believe me, I know. I've looked."
The female Genie in the series, on being let out of her lamp, asks if she's missed the Gold Rush (which happened in 1849). Apparently she's seen the far future too.
Hercules itself, particularly the animated series. Herodotus (5th century BC) is Herc's history teacher. Elucid (2nd century BC) teaches math. Ptolemy (1st century AD) teaches astronomy. And Homer (9th century BC, according to Herodotus) is a local reporter. There's more leeway for the mythological figures, who don't have dates attached to them, but Achilles is an elderly hero everyone's forgotten, even though Helen of Troy is in Herc's class!
And in the movie, when Herc arrives in Phil's house the Argo's mast is there... while in the myth, Hercules was one of the Argonauts. (though the series kinda Hand Waves this: Jason didn't find the Golden Fleece the first time around, so Hercules joins him in another attempt)
The Land Before Time stars an Apatosaurus and a Stegosaurus, both of which existed in the Jurassic period, alongside a Triceratops, a Pteranodon, a Parasaurolophus, and a Tyrannosaurus as a villain, all of which existed many MILLIONS of years later in the Cretaceous period.
They meet a Dimetrodon from the Permian (The period BEFORE the dinosaur age) halfway through the movie.
How can this be anachronistic? According to the title of the movie, time hadn't been invented yet.
Mulan, despite taking place in Imperial China, portrayed all of the male soldiers fighting for the Imperial Army as wearing boxer shorts under their armor! (one of which has the iconic red heart pattern, which is then flung at Mushu's face during the scene where Mulan and her friends Yao, Ling, and Chien-Po go skinny dipping in the lake) However, for some reason, they never show what Mulan's own underwear actually looks like (she may either be wearing traditional Chinese undergarments that are completely relevant to the film's setting and time period, or she may be wearing a bra and panties under all of her outfits to complement the aforementioned boxers).
Actually, they do show Mulan in her underwear at one point: About halfway through the song "Honor To Us All", Mulan can be seen wearing a white dress underneath her iconic pink one, which can be seen completely (although she was sitting) when she is having her hair done. What appears to be her pajamas at the very beginning of the film may also serve as her undergarments as well.
I Can Do Bad All By Myself: When Madea is trying to explain the account of Peter walking on the water, somehow Moses, Eve, Sigmund and Freud, and Jonah end up in the mix. Yeah they all were in the New Testament apparently.
Becomes extremely evident in Pixar's Cars 2 where all of the famous world landmarks are given car motifs to fit the fact that everyone in the Cars universe is a talking vehicle. The problem is, however, that most of these landmarks are actually more than a century old, long before any cars were even invented!
Adding to this is that whenever either the Cars versions of the Earth and Moon are seen from space, parts of the Earth's continents resemble either small cars or car parts, while the maria on the Moon resemble the grille of a car.
Napoleon Dynamite is basically made of this trope: The movie is set in 2004, yet the protagonist's fashion sense got stuck somewhere in the 80s. His uncle Rico is even worse in that regard, since clothing-wise he's all set up to go on a 70s disco binge. Napoleon's portable music device of choice is a Walkman and his brother Kip hooks up with "chicks" online by means of a 90s-era dial-up connection, which is not surprising since in the movie's setting no one seems to have even heard of cordless phones and rotary dials still seem to be pretty commonplace.
Plunkett And Macleane has two characters who are the embodiment of this trope, Dixon and Winterburn, despite being aristocrats from ~1750 are very fond of phrases such as "geezer" and "nicely" said in the fashion of parodies of 1980-90 northerners for laughs. This is semi-lampshaded by Rochester (who is much more of the era in tone, although not in behaviour!) when he describes them as eccentric and "dear". The fact that by the time the movie was made the terms and phrases used by Dixon and Winterburn are themselves anachronistic, must surely score extra points.
Cabin Boy is filled with them. Modern limousines combined with ocean liners being the only method of long distance travel, a boarding school out of the 1800's. A fishing boat using old hemp nets yet also having a microwave.
In TMNT, four Aztec generals from over 2000 years ago are named with Spanish names. Not only did the Spanish language not exist back then, but it would not arrive to Mexico till after 1492 AD. Also includes Spexico.
The presence of Aztec generals is a major case of Newer Than They Think, too. The Aztec empire was created in the fourteenth century, and the ethnic group first came into the area around 6th century AD at the earliest.
Made even worse when you consider that the main antagonist's 'trophy wall' shows that after that after that event 2000 years before, he went on to become an Egyptian pharaoh, implied to have been the founder of said civilization. except that said civilization was founded almost 6000 years ago, and ended before 2000 years ago. the whole film works much better if you assume an extra zero or two to the given date and a 'conan the barbarian' type lost age..
Brave, which takes place in medieval Scotland (somwhere between the 8th and 12th centuries), does make some attempt to be historically accurate, but it still has corsets, which weren't invented until centuries later, along with the plaid (15th-16th century) & kilt (18th century); forks (16th century); Shire horse (breed developed in the mid-17th century); Highland games (19th century, and Canadian); bagpipes (14th century); the word "chortle" (19th century); fighting the Romans (1st-5th century), Vikings (8th-11th century) and bears (extinct in Scotland between the 1st and 10th century) at the same time.
Whilst it wasn't using Rule of Funny, the British film Caravaggio, notable for an early appearance (and, in some ways, the Breakout Role) of Sean Bean, is a deliberate anachronism stew, in homage to the Real Life Caravaggio's paintings, which depicted Biblical scenes in contemporary dress.
In the flashback to Davey's childhood in Eight Crazy Nights, Whitey dances to Styx's Mr. Roboto. The flashback in question took place in 1981, the song didn't actually come out until two years later.