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Pirates
Stede Bonnet
Played by: Ordinary Things
The titular Gentleman Pirate. A wealthy Barbadian sugar plantation owner who eventually turns to piracy.
- Bookworm: What sets him apart from all the other pirates. Not only is he literate, but he really enjoys books. To the point where he commissions his custom sloop (which was designed for piracy) to have a library.
- Classical Anti-Hero: He certainty proves to be a sorry excuse for a buccaneer. Even after he improves at being a pirate, he just becomes worse in other ways.
- Disappeared Dad: Applies to both Stede's dad and Stede himself. Bonnet's father dies when Bonnet was only 6, and Bonnet later abandons his own children.
- Dressed to Plunder: Stede dresses like a pirate even before he decides to turn to piracy.
- Et Tu, Brute?: He feels personally betrayed when it's revealed Pell ratted him out in exchange for a plea deal.
- Stede Bonnet: Pell, how could you? Remember the ship scuttle scene from about ten minutes ago? And how you held me in your arms?
- Good Parents: Although his father died when he was young, Stede's mother raised him educated and with the advantages minor nobility offered, like clean water. When Stede's father returns as a spirit, he at least attempts to give advice to his son, even if that advice is very useless.
- Henpecked Husband: Stede was this in his marriage with Mary Allamby, which ended up pushing him to become a pirate.
- Heroic BSoD: Bonnet has one when the quartermaster is killed in the Battle of Cape Fear River.
- Horrible Judge of Character: Can't detect Blackbeard's ulterior motives even if it's extremely clear.
- Lovable Rogue: The citizens of Charleston saw Bonnet as a charming rebel and didn't want him to be punished. Even Governor Johnson directly describes him as a "lovable rascal".
- Medium Awareness: At one point, he speaks directly to the audience and states "I'll do the exposition for a bit!" before proceeding to enthusiastically narrate.
- Never My Fault: In the letter he wrote to Governor Johnson (not shown in the film but described in a side note), he admits no fault for his actions, blames other people, and overall throws a pity party for himself.
- Same Clothes, Different Year: Downplayed. Since he was young, Stede Bonnet has always dressed up as a pirate, a habit that carried into his adult years.
- Took a Level in Badass: Became a more ruthless and efficient pirate after being double-crossed by Blackbeard.
- Wake-Up Call: After Blackbeard betrays him, Bonnet decides to get his act together, listen to the quartermaster (then one-eighthmaster) for once, and become a proper pirate captain.
Quartermaster
Played by: Internet Historian
An experienced pirate who acts as Bonnet's right hand man. Eventually demoted to one-eighthmaster, then promoted back to quartermaster. Bonnet leans heavily on his leadership.
- Everyone Calls Him "Barkeep": The quartermaster is only referred to as "Quartermaster" throughout the film, even in the credits. When his title changes to one-eighthmaster, he's referred to as such by the other characters and the Narrator.
- Excellent Judge of Character: He has the ability to read Bonnet's men better than Stede and can also detect Blackbeard's ulterior motives from the get-go.
- Hypercompetent Sidekick: One of the few people who knows the ropes at sea. Him being demoted to one-eighth master in favor of Ignatius Pell really put the crew into a string of bad luck. Then when Bonnet returns to save him and the crew from dying of starvation at the sandbar, he helps Bonnet become an effective captain.
- Ignored Expert: The quartermaster is chastised by Pell and the crew for questioning Blackbeard. And Bonnet, under the recommendation of Blackbeard, demotes the quartermaster to one-eighthmaster. Turns out, he was right to be wary of Blackbeard.
- The Lancer: To the Gentleman Pirate. While Bonnet is klutzy and incompetent, the quartermaster is rational and competent.
- No Name Given: The quartermaster is never given a proper name in the Sundance Reject.
- The Spock: Undoubtedly the most reasonable member of Bonnet's crew.
- Undying Loyalty: Despite being demoted to one-eighth master, being pushed aside for Pell, and even dying due to Bonnet's own decisions, the quartermaster is loyal to the very end.
Ignatius Pell
Played by: SumitoMedia
Bonnet's boatswain. Eventually promoted to quartermaster, then demoted back to boatswain.
- Drowning My Sorrows: Pell ends up as a drunk on the street after being freed. He regrets betraying Bonnet and alleviates his pain with alcohol.
- Feet of Clay: Vies for the position of quartermaster, but after his promotion, he leans toward rash, short-term solutions that look like safe bets but cause major problems later down the line.
- First-Name Basis: With Stede Bonnet. As his boatswain, Pell calls him "Captain." But after Bonnet loses his crew and is no longer a captain, he continuously calls Bonnet "Stede."
- Get A Hold Of Yourself Man: He slaps Bonnet two times after his attempted Heroic Suicide.
- My God, What Have I Done?: After ratting on Bonnet, he then testified against him. Only when at the docket, actually defended Bonnet's character and said that the quartermaster holds the decisions. The judge ignored it, saying that Pell said otherwise in writing and sentenced Bonnet to death anyways. Pell became distraught, and after catching wind of a letter from Governor Johnson, rushed to deliver it to the executioner before Bonnet would die in the gallows... only for the said letter to not be a pardon, but approval of the execution.
- What Happened to the Mouse?: Pell isn't shown in the alternate good ending. It's not sure what he did after Stede, his children, and the quartermaster sped off in a speedboat full of gold and left Pell in Charleston.
Blackbeard
Played by: SumitoMedia
The most famous pirate. A ruthless leader known for putting fear into his enemies' hearts. Bonnet runs into him in Nassau where they decide to team up.
- The Ace: Blackbeard is good at what he does. Even King George can't help but compliment his skills.
- Anti-Villain: Blackbeard turned to piracy because he saw no other choice. It was either that or unloading cargo in Bristol like his father until he died. Ultimately, he's still the antagonist in Bonnet's story.
- Hero of Another Story: He's been pirating longer than Stede and has earned himself a gnarly reputation. After splitting ways with Bonnet, he went on his own adventures, eventually ending up dying at the hands of British soldiers, only after a ferocious and bloody battle.
- Talk Like a Pirate: He speaks in the cliche pirate accent.
David Herriot
"Aw shit, innit!"
Former ship's master of the ship Adventure before it was captured by Blackbeard. Joins Blackbeard's crew and eventually Bonnet's.
- Cloudcuckoolander: Very much this, and when asked why he was still here, the quartermaster described him as "a no-nonsense guy with a heart of a captain and a great sense of humor."
- I Am Very British: Mostly subverted. Herriot has a very exaggerated English accent but never speaks or acts posh. He acts quite the opposite.
- The Thing That Would Not Leave: Nobody knows why he was still there on Bonnet's ship after they were rescued, the side notes mention "he just kind of hung around."
- Verbal Tic: Has a tendency to punctuate his sentences with "innit" no matter the situation.
Landlubbers
Mary Allamby
Played by: SumitoMedia
Stede Bonnet’s nagging wife (and eventual ex-wife).
- Fate Worse than Death: Bonnet and his crew are stuck with two options; nullify Bonnet’s pardon and plunder to gain resources or risk starvation. The former is risky and if they’re found, they’ll be hanged. Pell jokingly mentions a third option: return back to the farm with Mary. In which Bonnet chooses the first option without a thought.
- Jerkass: Berates Bonnet despite his best efforts to fix the troubles on the farmstead, going as far to toss Bonnet’s miniature ship out the window, accidentally causing the death of their son, Allamby. When she remarries David Rycroft, she gives him the same nagging treatment.
- Overly Long Scream: "STEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEEDE!"
Bank Teller’s Son
“Grr, I hate pirates.”
The loud-mouthed son of Stede Bonnet’s former bank teller. After Bonnet lets a pirate rob his father’s bank, the bank went out of business, causing his father to lose his job and spend his days drinking alcohol. Because of what happened to his father’s bank, he hates pirates with a burning passion. He inexplicably ends up in Charleston some time before Blackbeard blockades the port and becomes a courier.
- Bratty Half-Pint: He never refrains from speaking his mind. He’s stubborn and, well, bratty. He’s described as a “little shit” by his own dad.
- Chekhov's Gunman: Is introduced at the beginning without any lines. He briefly reappears during Blackbeard's blockade of Charleston. When he returns near the end, he plays major role in the final struggle.
- Jerkass: Other than being a whiny brat, he's super stoked for Bonnet's execution. He tells Bonnet how he can't wait to see the life "sap out of his eyes."
- No Name Given: The bank teller’s son is never given a proper name, only being referred to as “kid” by the other characters.
- Smug Snake: Has his list of overly smug moments, including flipping people off and teasing Pell with what he assumed to be Bonnet's pardon.
Colonel William Rhett
Played by: Internet Historian
A colonel in provincial South Carolina's militia.
- Punch-Clock Villain: Colonel Rhett is just following the orders of Governor Johnson when pursuing Bonnet. It's part of his job as a colonel.
Governor Robert Johnson
Played by: Internet Historian
The British colonial Governor of the Province of South Carolina.
- Foe Romance Subtext: Johnson carves wooden figures and kisses posters of Bonnet during his "private time." He even goes on to call Bonnet a "handsome bastard" and "lovable rascal."
- Villainous Crush: Obsessed with Stede. A bit too obsessed. As in wanting to throw the book at him yet kissing his images in private. He seems to be attracted to Stede's lack of respect for the law.
