1. Drunk Histories
The formula is simple: Take historical events, teach them to someone, and then get that person really drunk. Have the person retell the historical events in their inebriated state, and then film a re-enactment of precisely what they say, using famous actors and comedians. The end result is Meriwether Lewis (played by Tony Hale) and his crew being confronted by the Lakota "Indrians" and being saved from death by a tribal chief who demands, "You know what? Chill out. Everyone chill out!" While the episodes make for terrible study guides, they are great starting points for historical discussion, preferably ones conducted late at night in frat houses.
2. The Open University's History of English
The Open University uses a series of 10-minute animated skits to tell the history of the English language. In the process, they tell the history of half the world, with plenty of jokes thrown in. From the Norman Conquest to Internet English, the History of English series is a great way to sneak knowledge into your brain while being entertained.
3. History for Music Lovers
Although working with the lowest production values (absolutely none, according to the group's Facebook page) on this list, History for Music Lovers takes great care with its subjects. Each video is a silly musical parody of a popular song, with the lyrics changed to tell the story of the historic person or event. The videos are a labor of love, produced by real teachers hoping to create a fun way to teach history. Soft Cell's "Tainted Love" becomes the perfect tune to teach about the Trojan War, and the history of illustrated manuscripts is explored with The Beatles' "Nowhere Man."
4. Horrible Histories
Horrible Histories comes to us from Britain, a country that has mastered the art of dark humor. The BBC produces Horrible Histories knowing that the most interesting parts of history are weird and awful. Each "Horrible History" is a short comedy skit highlighting the funniest possible parts of the subject — no matter how dark — enticing the viewer to seek out further information. There is much to be learned by watching Harriet Tubman madly wave a chicken in the face of a slave hunter, or by enjoying a rousing musical rendition of how the Black Plague decimated Europe.
5. Epic Rap Battles of History
What would Babe Ruth say to Lance Armstrong if he were alive today? Or rather what would he rap? Comedians-musicians Peter Shukoff and Lloyd Ahlquist's series Epic Rap Battles of History teach a wealth of information as a byproduct of rhyming insults. You can learn about Stalin (vs. Rasputin), Shakespeare (vs. Dr. Seuss), and Hitler (vs. Darth Vader, of course), just to name a few. The videos are excellently made, very funny, and usually vulgar. So while not appropriate for everyone, those who do watch will likely never forget the history they hear, such as who Cleopatra dated and how she died.
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