10 Historical Comedies To Watch After ‘Our Flag Means Death’

Many people associate history with stuffy books and long hours of monotonous research. Fortunately, many writers and filmmakers have sought to liven things up a bit by putting a comedic spin on some of history’s most serious moments. David Jenkins is the latest creative to offer “historical stories” with his TV show Our flag means death become a huge hit on HBO Max .

Related: How ‘Severance’ and ‘Our Flag Means Death’ Offer Thoughtful Queer Representation

But this pirate comedy, starring Rhys Darby and Taika Waititi, is just the latest in a long line of comedy movies and historic TV shows. So if you’re craving more historical hijinks after this season finale, here are some options to get you through to Season 2.

drunk story (2013-2019) – Sometimes the story is too much to handle sober

drunk story

You can’t talk about historical comedies without mentioning this brilliantly absurd little gem. springing from the spirit of Derek Waters and originally from by Will Ferrell website, funny or die before moving to Comedy Central, this series has a delightfully simple premise: celebrities try to recount events from history while getting drunk.

As you can imagine, this usually leads to some hilarious and not quite accurate stories. Tales that are then staged by actors to really amp up the absurdity. For an extra Our flag means death connection, check out the Australian version of the show, which features Stede Bonnet himself, Rhys Darby.

Handyman (2000) – Bruce Campbell stars as the greatest spy in history


Set in the early 19th century, this short-lived and often forgotten series stars a beloved actor Bruce Campbell as an American secret agent named Jack Stiles. Sent to the East Indies by Thomas Jefferson, Jack works with the English spy, Emilia Rothschild (Angela Dochin), to combat threats to America, such as Napoleon Bonaparte (Verne Troyer).

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The show features a parade of comically biased historical figures, romantic tension between the two leads, and even sees Stiles frequently don a mask as the heroic “Daring Dragoon.” As a bonus, not only is it set in a locale similar to Our flag means death, but it even features Blackbeard.

plebs (2013 – Present) – Modern Issues in Ancient Rome


Created in 2013, the British series follows a group of characters trying to navigate life in ancient Rome. Initially following Marcus, Stylax, and their slave Grumio after moving to the big city, the characters come and go over the course of the series. As with most comedies in this vein, it transplants modern ideas and story elements into an anachronistic setting.

Even though its final season aired in 2019, it’s still technically continuing as a special is on the way which will serve as the series finale. Plus, it’s another show with a connection to Our flag means deathsince Stylax is played by Joel Frywho you might recognize as Frenchie from this series.

Maid Marian and her merry men (1989 – 1994) – A revisionist version of a classic tale

Maid Marian

Even though the Robin Hood legends are of questionable historical accuracy, this series can still be considered historical, because why not? From 1989 to 1994, this BBC series challenged traditional legend by placing Maid Marian center stage. Robin, on the other hand, is portrayed as nothing more than a vain tailor who accidentally gained a reputation as the leader of the gang.

Created by Tony Robinsonof black viper fame (more on that later), the series was a big hit and in many ways was ahead of its time. This show was ahead of its time and well worth a look through a modern lens.

A Million Ways to Die in the West (2014) – A Wild and Savage Western

A Million Ways to Die in the West

Although he is best known for his work on family guy, Seth McFarlane had one of his first starring roles in this western comedy. Directed and co-written by MacFarlane, this film uses his trademark sense of humor to ridicule many Western stereotypes and underscore just how horrible the period would have been.

Co-starring Liam Neeson, Charlize Theron, and Neil Patrick Harris, plus some unexpected cameos, it may not have been a critical success, but fans of MacFarlane’s style will love it. With one of MacFarlane’s other films, Tedrecently announced getting a TV seriesmaybe we could see more ways to die in the west someday too.

Blazing Saddles (1974) – The Trail-Blazer That Defined a Genre

Blazing Saddles

It is undeniable that Mel Brooks revolutionized film parody with its classic 70s and 80s comedies. One of the biggest and most beloved of these was Western parody, Blazing saddles. Set in 1874 and featuring little cleavon as Bart, a black railroad worker turned sheriff, and Gene Wilder like his sidekick, The Waco Kid, a failed shooter.

Related: Mel Brooks Movies Ranked From Worst To Best

At a time when Westerns were still wildly popular, Brooks turned the genre upside down by weaving in a crazy comedy that crumbles in the best possible way at the end. Commenting on everything from racism in America to classic movie tropes, it’s still going strong almost fifty years after its release.

Upstart Raven (2016 – 2020) – This is how Barding should be taught in schools

Upstart Raven

Any student will tell you that studying Shakespeare can be a lot of work, but this series manages to tell The Bard’s story in a fun way while honoring his genius. From the mind of the comic genius Ben Eltonthe series depicts Will’s life from 1592 as he attempts to make a name for himself as a poet and playwright in London.

He uses anachronisms to draw parallels to the present, not just for comedic effect, but to make the characters easier to understand. Plus, Elton’s clever writing means the series isn’t just entertaining, it’s also quite educational.

Monty Python and the Holy Grail (1975) – The Stuff of Legend

Holy Grail

Another that straddles the line between history and fantasy, this is by far one of the most beloved films to come from the minds of Monty Python comedy troupe. Taking a unique Python approach to Arthurian legend, the story sees regular Python Graham Chapman as King Arthur as he searches for the Holy Grail.

Infinitely quotable and full of memorable gags, this film has achieved cult status and often tops lists of the greatest comedies of all time. If you haven’t seen it, grab some coconuts and make it your personal quest to seek it out.

History of the world, part 1 (1981) – The Only History Lesson You’ll Need

world history

Another Brooks classic, this film is split into multiple vignettes, each parodying a different era in human history. It’s full of quotable lines and features a host of celebrity cameos.

The “Part 1of the title was originally meant to be a joke, as was the movie’s teaser for a sequel, with Brooks never intending to produce a sequel. However, Hulu recently announced that a sequel is in the worksso you better revise your history by looking at this first.

black viper (1983-1999) – Take Rapier Wit in every period of history

black viper

It is undeniable that when it comes to historical comedy, there is not much better than the black viper franchise. Featuring British comic royalty, Rowan Atkinson and written by people like Atkinson, Richard Curtis and Ben Elton, black viper is a cultural institution. It’s not a singular television series, but rather four related series and several specials, all set in different periods of history, featuring different members of the Blackadder family.

From the court of Queen Elizabeth I, to surprisingly harrowing moments in the trenches of World War I, this franchise has vast scope and an unparalleled level of snark and wit. It is a historic program in more ways than one.

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