Being a pirate is alright to be
As usual, credit for list-maker goes to Meandering Banter: https://meanderingbanter.blogspot.com/2018/10/automatic-list-to-html-translator-v2.html
D20x5 Strange Sailors
D20|This Sailor Has Sailed...
1|A bit of every ocean on the map.
2|Their whole life. They’ve spent more time on a boat than off one.
3|The Guanocean, a tremendous and smelly outflow of guano from a massive cave system. It’s trawled for fertilizer, though tick-sharks are a constant threat.
4|The headwaters of the River Styx.
5|As both a pirate and a merchant.
6|Between the pillars of the Starlit Sea, which mark the boundary between reality and dreams.
7|Far less than they claim to.
8|Across deadly waters claimed by man-eating mermaids.
9|The acidic sea which lies down the throat of Charybdis.
10|The Upside-Down Sea, the remnant waters above the sky left after God called down His deluge.
11|Only ever one route, which they know by heart and could navigate in total darkness.
12|A lake in the bowl on the head of a gigantic kappa.
13|A sea where the winds fear to blow, which they escaped by the skin of their teeth.
14|The Clotted Sea, which gouted from the neck of a slain beast.
15|Up a waterfall, by means they never clearly explain.
16|The Mush, a great lake of tar and petrochemical-eating slime molds.
17|The Sargassium, where all lost things eventually end up.
18|A shallow strait where coral rises like bleached mountains above the waves.
19|The Sandsea, a desert with grains so fine they behave like a liquid.
20|The Well of the Unwise, a freshwater sea that spilled from a broken, tainted Mimisbrunnr.
D20|This Sailor’s Favourite Story...
1|The time their boat capsized, and they wound up in a world that exists in the reflections on the water’s surface.
2|Is the heavily embellished account of how they hooked up with a mermaid
3|Downplays the severity of an atrocity they participated in.
4|Is long and boring, and they’ll be insulted if you don’t listen to the whole thing.
5|Is one they’ll only tell while black-out drunk.
6|Takes the form of a sea shanty.
7|Is one they stole from someone else and put themself in the leading role of.
8|Is the time they mutinied against a cruel captain.
9|Has nothing to do with sailing.
10|Reveals the location of a buried treasure.
11|Gives an unflattering perspective on a famous figure.
12|Contains a simple moral lesson.
13|Has been passed down their family for generations.
14|Involves an encounter with a rare monster, and reveals the thing’s weakness.
15|Is the time they were left for dead but persevered against all odds.
16|Is memorized from a popular serial novel. The first thing they do on returning to port is see if a new issue of it has been released.
17|Is an epic poem about mythological heroes.
18|Implicates them in some very illegal activities.
19|Is about why they chose to become a sailor.
20|Is raucous and bawdy.
D20|Among This Sailor’s Tattoos Is...
1|A person tied to an anchor trailing down their back. The person looks terrified. The person isn’t the sailor.
2|A kraken with the tentacles trailing down one arm. Circular scars on the arm are worked into the tattoo, as if they were the kraken’s own suckers.
3|A list of names, the letters so small and so crowded as to be nearly illegible. The names of everyone the sailor has ever met.
4|A compass on the back of their hand. Its needle always points north.
5|A map with their home marked prominently.
6|A pair of eyes on the back of their head.
7|A sunset in photorealistic detail covering their chest.
8|A sea serpent wrapping around a leg. Its head is crushed under their heel.
9|A ruler along the inside of their arm, with various measurements marked on it.
10|Crimson tears that dot their cheeks. Each time they kill someone another will appear.
11|A collection of cutaway diagrams of various species of fish, showing the best way to filet each.
12|Permanent makeup, eyeshadow, lipstick, the works. The wager of a lost bet.
13|An albatross with wings curving around their shoulders.
14|An eel waving up one leg and down the opposite arm.
15|A skeleton that chugs a bottle of rum when they flex.
16|An enchanted glyph that stings the eyes if stared at. It makes them more buoyant.
17|Lips on their cheek that whisper with the voice of a lover in their ear when they sleep.
18|Themself depicted as a mermaid.
19|A dozen prayers to river spirits that weave around their mouth and chin. Their blessing allows the sailor to safely drink seawater.
20|A rope that ties itself into any knot the sailor can imagine. They amuse themself by watching it change.
D20|This Sailor’s Salty Superstition...
1|Forbids them from working on ships with unequal numbers of men and women.
2|Is to kiss a boat’s figurehead before every voyage. If there is no figurehead then one must be carved.
3|Is that wearing a red handkerchief on every third day will protect them from sharks.
4|Is that people who die at sea will become vicious storms unless their bodies are buried back on land.
5|Makes them fear dancing. Even tapping your foot along to a beat could be disastrous.
6|Drives them to carry a handful of sand from the last beach they laid foot on.
7|Is to carry their baby teeth around with them, and cast one away each time they survive a near-death experience. When the teeth run out they’ll know their luck has left them.
8|Demands that they leave an offering for storm-spirits each time they return safely to shore.
9|Is that enough grog rations can cure any disease.
10|Is that seabirds report everything they see to the gods, and so will not swear, fornicate, or blaspheme within sight of them. Very fond of these things otherwise.
11|Is that shaving would rob them of their good fortune.
12|Prohibits them from looking a priest or wizard in the eyes.
13|Is that a ship must be respected and treated like a beloved pet.
14|Is that you can tell a person’s future from their scars.
15|Requires them to accept only things that can float as payment.
16|Is that people who will not spit together are untrustworthy.
17|Is that they must get the same tattoo as any captain they serve under, or give the captain a tattoo if they don’t have one.
18|Is that married folk are bad luck on a boat.
19|Is that any gambling taking place on the ship must leave a seat open for a sea god.
20|Is that all blood shed at sea must be repaid by an equal amount of beer poured into the water.
D20|This Sailor Will Work...
1|For a pittance. No one familiar with their reputation would hire them otherwise.
2|Free for anyone who reminds them of their first captain.
3|Any job that doesn’t require them to fight.
4|For you at a discount if you resolve their legal troubles in port first.
5|Only if you hire their friends as well.
6|At a premium. They’re worth it.
7|At exactly the market rate. They’ve got their ear to the ground when it comes to changes in sailor employment.
8|For a reasonable amount but bug out the first time things get rough.
9|Jobs that bring them to exciting new vistas.
10|If they’re taken on as an apprentice by someone who’s got some skill they don’t possess.
11|For captains that allow them to do some smuggling on the side.
12|Better under a captain with proper military experience.
13|Confidence games while in port to earn extra money.
14|For the benefit of the less fortunate.
15|For only one voyage on any ship.
16|Exclusively jobs that are above-board legally. A notorious but well-connected snitch.
17|One last job before retiring. They’re getting too old for this shit.
18|Just to pay off their bills from various soothsayers and courtesans.
19|For anyone who can pay their price no matter the job.
20|On land as well if the pay’s good enough.