OSR: GLOG Pirate Classes

Core Classes

In the GLOG format. Multiclassing is encouraged. By blending the 6 Core Classes (Artillerist, Brawler, Duelist, Philosopher, Smooth Talker, and Weather Witch), you should be able to get any strange pirate you desire.

Artillerist

A slightly modernized version of this class.
 
Starting Equipment:  2 pistols, rifle or blunderbuss, 12 charges, dagger 
A: Bombard's Eye, Gunnery Master
B: Bomme-Maker, Smouldering
C: Impossible Shot
D: Quick Reload, Scorched

Bombard's Eye
If you fire a ranged gunpowder weapon at a stationary or nearly stationary target and miss, your next Attack roll against the target gains a +4 bonus. This bonus does not stack with multiple attempts. If you would only  hit on a critical success, you still only hit on a critical success.

Gunnery Master
During ship-to-ship combat you can choose one shipboard weapon. It gains +2 range.

Bomme-Maker
You can rapidly craft a crude but controlled gunpowder bomb without any risk or skill check. Crafting requires 2 charges and some added shrapnel. It takes 2 rounds. The bomme deals 2d6 damage in a 20' radius. The fuse can be set to any time, from instant (explodes in your hand) to 10 minutes. It can be thrown (as a dagger). It can also be used to open doors or crack stone.

Smouldering
If you make a charge attack with a gunpowder weapon (or any other sufficiently surprising attack), and kill your target, enemies who can see the attack must make a Morale test. You don't have to light your beard on fire and scream but it helps.
 
Impossible Shot
Once per combat, you can make an impossible shot with a pistol or musket. The shot can strike a target around a corner, cut a falling coin in half, or ricochet half a dozen times before parting the hair on a hostage's head. The shot automatically hits. Roll for damage normally.

Quick Reload
You reload gunpowder weapons in 1/2 the usual time. In ship-to-ship combat, once per combat,  you can select a weapon to fire twice.

Scorched
You take 1/2 damage from fire. If your weapon would misfire, it simply fails to fire this round and can be fired normally in the next round.

Mechanical Notes on the Artillerist
You're good with anything that goes "boom". Rules for pistols, muskets, etc. will be included in a separate post.

Brawler

Starting Equipment: sword, 2 pistols , 6 charges
A: Parry, +1 attack per round 
B: Notches
C: Cleave, +2 Attack stat
D: Leathery

You gain +1 HP for each Brawler template you possess. In ship-to-ship combat, you count as 5 Marines for each Brawler template you possess.

Parry
Once per day, you can reduce incoming damage by 1d12 points.

Notches
Each time you attain a total of 10, 20, 30, and 50 kills with a weapon type (such as 10 kills with a dagger), you unlock a new ability for that weapon, chosen from the list below. Keep track of your kills and special abilities.
1. +1 Damage
2. Expanded Critical Range (+1)
3. Special ability (negotiated with GM, one per weapon)

For example, a Brawler with 50 sword kills (4 notches) could have +1 damage, a critical range of (1-3), and the ability to stun an opponent for one round on a critical hit. The GM decides what counts as a kill. Cannons don't count. Pistols, muskets, and your bare hands do.

Cleave
Whenever you reduce a creature to 0 HP with a melee attack, you can make another attack with the same weapon against a target within 5’. You can only cleave an number of targets equal to your Level in a single round.

Leathery
Reduce all incoming damage by 2 points. You gain a +2 to Save vs mind-altering spells. You have 4 rounds to remove your Fatal Wounds instead of 3.

Mechanical Notes on the Brawler
Since any kind of armour is relatively uncommon, more classes have damage-reducing abilities. The Brawler is the best fighter right out of the gate, but when all you have is a murderous hammer, everything looks like an easily murdered nail.

Duelist

Starting Equipment: sword, pistol, 6 charges, dagger, fancy hat
A: Lone Combatant
B: Impress, Lucky 
C: Call Out,
D: Choice Weapon, Very Lucky
 
You gain +1 to Movement for each Duelist template you possess.

Lone Combatant
Each time you defeat an enemy in one-on-one combat or a Duel (see below) keep track of what type of weapon they were wielding. You get +1 Defense against that type of weapon. This ability cannot raise your Defense higher than 16. You gain +1 to your roll for a Duel.

Impress
Whenever you win a fight or a Duel against a challenging enemy, people who don't like you make a new reaction roll with a +4 bonus. This even works on people you just defeated in combat, unless you caused them undeserved or disproportionate harm.

Lucky
You may reroll 1 d20 per session.

Call Out
This ability only works on creatures that can understand you and are capable of being offended. If you challenge a creature outside of combat, they must make Save to resist accepting. In civilized areas, this is basically a duel, and this means that you and the other party must agree upon the time, the place, the weapons, the victory condition, and the stakes. Leaders will usually send out a champion to fight in their stead (if applicable). In combat, you can challenge one creature each turn by yelling at it as a free action. The creature must Save . If they fail, they will attack you. This ability cannot force an opponent to make major tactical errors or leap off cliffs.

Choice Weapon
Choose a weapon type (dagger, sword, pistol, rifle, cannon). You gain +2 to your Attack with that weapon type. 

Very Lucky
You may reroll 2 d20s per session. Once, ever, you can reroll a d6 in a Duel.
 
Mechanical Notes on the Duelist
A flair for the dramatic and dangerous and desperately risky. Duelists have no way to reduce incoming damage, but they can certainly dish it out. 

Side Note: Rules for A Duel

This is for proper, formal, short, and brutal duels between two mortals of approximately equal skill.

Both sides roll 1d6. Highest roll lives. On a tie, if 1-3, both sides are unharmed. If 4-6, both sides are wounded and at 0 HP. If 7+, both sides are dead.

Gain +1 to your roll if you have fought in a duel before.
Gain +1 to your roll if you are totally, utterly certain that you want to kill your opponent and that you are able to kill your opponent.
Gain +1 to your roll if you are willing to die to kill your opponent.

Dueling is short, tense, and deadly. It's for duels at dawn, duels in the forest, duels in the cemetery. Some people like risking it all on a roll of the dice. If you want a less harsh version, just have the duel inflict a Fatal Wound or an Injury.

Philosopher

Starting Equipment: 3 books (any subjects), ink, quill, paper, dagger
A: Book Learning, Literacy
B: Obscure Knowledge
C: A Reputation for Wisdom, Deep Learning
D: Danger Sense, Self Control

You gain +2 to Save vs Fear for each Philosopher template you possess.
 
Book Learning
Choose a Skill from the following list or suggest your own: Surgery, Botany, Zoology, Folklore, Religion, Poetry, Literature, Navigation.

Literacy
You can read and write. Most people can do both, but you can really write.Your letters can allow for Charisma tests at a distance. You can roll to see the intentions of an author, the delicate themes of a poem, and the inconsistencies in a complex text. To most people this is a kind of sorcery.

Obscure Knowledge
Once per session, you can declare something is to be true because you read it in a book. The base chance of the thing actually being true is 50%. There has to be a plausible way you could know about it from reading books (new discoveries, minor details, and personal secrets are unlikely). You don't know whether or not it is true right away; the GM will roll when it matters. You might only be partially correct, but you will never be catastrophically wrong. If you declare that bugbears fear albino goats, they will either fear albino goats or be indifferent to albino goats. They won't be driven into a murderous rage by them. If you have access to a library of 50 books, the base chance increases to 80%.

A Reputation for Wisdom
If there's a weird problem, people will go to you first. If there's a mutiny and you aren't part of the cause, you will be spared. Once per session, you can give a command to someone and they must Save or obey it.

Deep Learning
Gain 2 other skills from the Book Learning ability.

Danger Sense
If you are surprised, you have a 50% chance to act on the surprise round anyway. If you encounter a creature no one in the group has seen before, you can roll under your Intelligence to remember a detail or weakness, provided the creature is not unique.

Self Control
You ignore the effects of previous Injuries when rolling on the Death and Dismemberment table.

Smooth Talker

Some ideas borrowed from Joseph Manola's Rake class.
Starting Equipment: sword or pistol and 6 charges or dagger
A: Evaluate, Winning Smile
B: Fast Talk, Flighty
C: Prominence
D: You Mean This?

You gain +1 to Stealth for each Smooth Talker template you possess.

Evaluate
You know the market value of any mundane item. Unique items may require an intelligence test to evaluate.

Winning Smile
As long as no bloodshed has taken place, you get a +1 bonus to all reaction rolls as long as you are the one doing the talking.

Fast Talk
You are an expert blatherer, liar, punner, and trickster. You can persuade any number of people of that whatever you are saying is true for 1d6 minutes, provided it is not obviously untrue. Sober, angry, and intelligent people get a Save to negate. When the effect ends, they realize whatever you've been saying is utter nonsense. They'll be very angry with you and immune to any future use of your Fast Talk ability.

Flighty
If you choose not to attack in a round your armour counts as Plate (16 Defense). This only applies if you can see your enemies. 

Prominence
Once per round, you can choose to be the most prominent person in a group or the least prominent person in a group. This does not give you any bonuses to stealth.

You Mean This?
Once per session, you can remove one non-obvious item from a person that mostly trusts you and has spent at least 10 minutes near you in the past hour. Not their sword or their hat, but a key, a trinket, or a letter, or half the wealth they carry. Before the hour is up, you need to tell them that you've taken it. Basically, you retroactively steal a thing.

Mechanical Notes on the Smooth Talker
No great threat in combat, but an interesting class on its own. Great for multiclassing, great for schemes.

Weather Witch

See this post.

The Crew

Adapted from Joseph Manola's Extras class.The crew cannot multiclass.
The Crew acts as one character. There are a lot of them (though the exact amount seems to vary from scene to scene) and they contribute about as much as one actual character (at best). They are a bunch of pirates milling about in the back of the scene, doing pirate things, kind of half-paying attention, and mostly serving as colourful detail.

Starting Item: sword(s), pistol(s), rags

A: Shared Totals, Mixed Bag
B: +1 Named Character
C: +1 Named Character, Use Thing
D: +1 Named Character, Surprise Arrival

The Crew gains +2 HP every level. If this would take them over 20 HP, they instead split into two Crews and lose half their maximum HP. One half deserts, tries to steal the ship, dies in a dramatic mutiny, or retires with their shares.

Shared Totals
The Crew has a shared HP pool just like a normal character. Every point of damage causes a single nameless pirate to die in an inconsequential background sort of way. Area of affect attacks and traps only affect them once. Single-target Save or Die effects instead cause the Crew to lose 1 HP in a dramatic way. Other single-target spells either affect the whole Crew or fail completely. GM's choice.

If the Crew is reduced to 0 HP, they become strewn about the place, wounded and moaning, miserable and unable to help anyone until healed. If they are reduced below 0 HP they all die in a suitably tragic-comic fashion. The only survivors will be the Named Characters, who are level 0 PCs with 2 HP, the Crew's stats, and no Templates.

If the Named Characters manage to recruit a new crew within 1 session, they can become The Crew again, at half their previous level. Otherwise, only one Named Character survives. When they next level up, they can choose to become one of the Core classes, or they can choose to roll up an entirely new Crew.

The Crew has 5 inventory slots total. They can carry more things but they will inevitably lose, smash, ruin, sell, or eat all but 5 items. Weapons and Charges are carried separately and do not occupy inventory slots, but they can't be used for special activities (you can't borrow a sword from them). In order to gain any benefit from a weapon or item, the Crew needs 10 copies. Give them 10 swords and they deal sword damage, etc.

They spend money collectively and irresponsibly. Count their XP against one share, not their combined shares.

If you need to determine exactly how Crew are present, roll 1d12+6. This number varies encounter to encounter and even round to round. When performing basic unskilled labour not related to piracy or sailing, like digging a trench or carrying buckets, The Crews count as 10 people for the first hour, 5 people the next hour, and give up after the third hour unless bribed or motivated. They occupy an area 20' square whenever possible, spreading as needed (a 5' wide 80' long line, etc.)

Mixed Bag
Roll a second Background when generating the Crew. Apply both results.

Named Character
One character in the swarm has earned a recognizable identity. Once per encounter, for one round, the named crewmember can do something different than the rest of the Crew. They could run to warn the PCs while the rest of the Crew fight something. At the end of the round, the Named Character is absorbed back into the swarm. Named Characters get a name and a short description like, "has a wooden eye" or "in a poor disguise."

Use Thing
The Crew can now be given unique items or special, possibly supernatural, tools. They can use them once per encounter, collectively. This could be a Named Character action. The crewmember with the giant blunderbuss fires it, then steps back into the crowd.

Surprise Arrival
At any time, the Crew may "walk off-screen." Later on in the session, they may re-enter a scene in a suitable piratical fashion: crashing through a window, slithering down ropes, leaping through the foliage. This ability is limited by plausibility.