History’s Most Terrifying Pirate Flags | Tales From the Bottle
Seeing the skull and crossbones approaching at sea was probably already pretty frightening, but for some pirates, it just wasn’t scary enough.
“The Jolly Roger was the ensign flown by a pirate ship preceding or during an attack, during the early 18th century (the latter part of the Golden Age of Piracy). The vast majority of such flags flew the motif of a human skull, or “Death’s Head”, often accompanied by other elements, on a black field, sometimes called the “Death’s Head flag” or just the “black flag”.
The flag most commonly identified as the Jolly Roger today – the skull and crossbones symbol on a black flag – was used during the 1710s by a number of pirate captains, including Samuel Bellamy, Edward England, and John Taylor. It became the most commonly used pirate flag during the 1720s, although other designs were also in use.”
More on Wikipedia:
https://en.wikipedia.org/wiki/Jolly_Roger
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@Qxir
June 6, 2026 at 9:44 am
While editing the video I realised I was probably a bit harsh on a number of the flags, but in my defence I did do the drawings after I ranked the flags, meaning the rankings were just based off the descriptions and other interpretations I had seen online.
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@dudmic
June 6, 2026 at 9:44 am
Now do the fictional ones from different Movies and Tv Series
@rickandmortyfan649
June 6, 2026 at 9:44 am
I bought 2 flags because of this video. Impulse buys, I tell ya
@DannyFiver-m9k
June 6, 2026 at 9:44 am
Who was Rogering him and is that why he was jolly
@abirdofafeather
June 6, 2026 at 9:44 am
6:58 Oh no, the dreaded Bohemian pirates, and their ship, the Rhapsody!
@shed7492
June 6, 2026 at 9:44 am
the white tears definitley should have came from the eyes of the skulls in the one with the bones crossed in the middle and four skulls
@deepwebintel
June 6, 2026 at 9:44 am
I think the decapitated head one would have been perfect if the characters were switched or tweaked slightly, i.e. The severed head be of the human with the guy holding it being the skeleton.
@connorferguson2269
June 6, 2026 at 9:44 am
Surprised how well detailed the flags actually are for pirate bands, guess they did have time on they're hands
@KlaxontheImpailr
June 6, 2026 at 9:44 am
Anyone remember the shows Cow and Chicken/I Am Weasel? They had a running gag about a character named Jolly Roger who would hang onto a flagpole singing about being a flag.
@SurrogateActivities
June 6, 2026 at 9:44 am
these remind of YouAreAnIdiot
@MidKnighToker
June 6, 2026 at 9:44 am
MOAR
@spitfire_2
June 6, 2026 at 9:44 am
I ❤ your drawings! ☠️🗡️
@bkhristorozhdestvensky180
June 6, 2026 at 9:44 am
The trumpet was in reference to Jericho. And what happened to Jericho? It fell literally. So what would happen to a ship if it's boards and planks and stuff with the pitch on it was to fall it would sink. I could be wrong but I believe that's what that trumpet is about.
@bkhristorozhdestvensky180
June 6, 2026 at 9:44 am
Oh there we go right after I hit play from you yeah Blackbeard was one of his names
@bkhristorozhdestvensky180
June 6, 2026 at 9:44 am
Actually I happen to be smoking a pipe right now. It's named after a captain actually. I only recently learned that it wasn't really a nice captain at all. In fact he was the equivalent of Genghis Khan of the sea. So the name shows a black ship I don't think there's any flag on there and we go look at my logo right now now I just see a bunch of sales anyhow you can look them up he's a very brutal bastard at least he was. He was known as Captain black. Go have a hoot at it and Google let me know what you think about something as benign As relaxing pipe to back I'll be named after such a sinister character. Oh and it would be no surprise that some carved pipes actually have faces of course one of them would be Captain black himself. I think you got that name from his black hair and beard and his brutality. I've also seen only in a couple of occasions I so wanted to buy it. There was one of Mr Hitler himself just as you know just his head while you're putting the tobacco in his brains and smoking the way like it's nothing. It was well done in fact artistically speaking. All right until your video as I was at the 4-minute Mark
@bkhristorozhdestvensky180
June 6, 2026 at 9:44 am
No no no no no no. Jolly Roger or is that jolly rancher? Damn. Isn't one of them a candy? Basically colored sugar barrel shape sort of cylinder shape wrapped in petroleum plastic?
@cascadianrangers728
June 6, 2026 at 9:44 am
4:15 i absolutely love this depiction of Teach
@cascadianrangers728
June 6, 2026 at 9:44 am
A smaller design on a flag that you cant read until they get really close would be extra scary
@CutestDemon
June 6, 2026 at 9:44 am
Imagine being a pirate, trying to create a cruel legacy of murder and riches, and your immortality of legend goes to "Eh, bullshit style, terrible vision, i'll give it an E"
@simonsemmler9804
June 6, 2026 at 9:44 am
if the tears were coming from the skulls like as if they were crying i think it would look way better
@Leatherargento
June 6, 2026 at 9:44 am
4:43 There used to be a comedian named Redd Skelton!
@TheVellar
June 6, 2026 at 9:44 am
Very interesting and educative.
@ThePigsmasher
June 6, 2026 at 9:44 am
was the skull over crossed cutlasses flag fictional or did you just forget it? cause that's the best one
@duncanread4442
June 6, 2026 at 9:44 am
8.30 time stamp.
Is that a grate relation to qxir? 😄
@o80y1
June 6, 2026 at 9:44 am
The American flag would work as a terrifying pirate flag too (provided that you can’t defend yourself with anti-ship missiles, torpedoes and drones)
@elliotberesford2826
June 6, 2026 at 9:44 am
Black flag red skelly is the best
@Yezpahr
June 6, 2026 at 9:44 am
I do think the "Gun and Sword" flag was a flintlock pistol and cutlass, instead of a cannon barrel and a sword.
@LFTRnow
June 6, 2026 at 9:44 am
"slightly different execution"
I see what you did there.
@SlayerEndX13
June 6, 2026 at 9:44 am
Might as well rate the One Piece flags…
@jeffreyrussell4874
June 6, 2026 at 9:44 am
The cross bones with 4 skulls made me think of Bohemian Rhapsody so I was bummed to see it given a low score. But apart from that most were done fair.
@aubs400
June 6, 2026 at 9:44 am
Bart Roberts was a Cymro/Welshman
@_Nobody_Special
June 6, 2026 at 9:44 am
A certain blue and white flag springs to mind. Albeit they have not been consigned to the dustbin of history. Not yet anyway, it seems like they’re working on it.
@Fkd-About-Found-Out
June 6, 2026 at 9:44 am
hmm i think i need a red flag
@Fkd-About-Found-Out
June 6, 2026 at 9:44 am
i bet you leave out the union jack…
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