Upstart Crow - comedy about Shakespeare, starring David Mitchell in a truly unflattering wig. Inaccurate as shit and also great.
Horrible Histories… OBVIOUSLY. I am sick of seeing people recommend Drunk History when Horrible Histories is right there, doing the Lord’s work. Watch this and tell me I’m wrong.
Blackadder - I 100% do not need to introduce Blackadder, because it’s Blackadder, but it’s Rowan Atkinson of Mr Bean fame being terrible and hilarious in many different time periods, and it includes Hugh Laurie as an Elizabethan dandy, so get on that immediately. Final series (set in WW1) ends with an actually heartbreaking scene that will ruin you spiritually. Love 2 laugh.
Plebs - sitcom about Roman peasants! Hilarious! They are, indeed, plebs who really just want to get girlfriends and have a nice time! Also there’s grain!
Quacks - legitimately ridiculously funny sitcom about Victorian doctors, starring many of the Horrible Histories cast. I would die for Mathew Baynton always, but especially in this. It was cancelled after season 1, which is despicable, but it’s still great. See for yourself!
Bill - a comedy film about Shakespeare, again by the Horrible Histories crew. It’s incredibly inaccurate and Shakespeare would have thoroughly approved.
I mean, I have to mention Monty Python’s Holy Grail (Arthurian japes) and Life of Brian, right? Like I’m contractually obliged to mention those? Good, because Life of Brian in particular is a fucking delight (follows a man who keeps getting mistaken for the Messiah when the real Jesus is RIGHT THERE, ACTUALLY, LEAVE BRIAN ALONE).
Another Period - a parody of Keeping Up With the Kardashians set in early 1900s Rhode Island. Weird as fuck, mostly because of how accurate it is.
The Madness of King George - a comedy drama, really, but Rupert Everett is hilarious in it. About King George III of England, who suffered from bouts of unexplained madness. Less devastating than it sounds, but also a bit devastating in parts.
‘Allo ‘Allo - a bit dated and definitely, erm, of its time (namely the early 80s-90s) but it’s set in WW2 and follows members of the French Resistance, some more willing than others. It has hilarious lines, but you do sort of have to watch with the acknowledgement that a lot of it is beyond the pale today. Mostly the sexist jokes.
The Bleak Old Shop of Stuff - Dickens parody set in Victorian England. Stars every British actor ever. Imagine a Dickens novel which knew it was ridiculous, and that’s this.
There are probably 900 more but I am merely one human and can only consume so much media, alas