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This wiki contains spoilers for all stories of Critical Role. This includes the story for unaired episodes of The Legend of Vox Machina, as it's based on the first campaign of Critical Role from 2015-2017.


Critical Role Wiki
Critical Role Wiki

"A Pirate's Life for Me" (2x41) is the forty-first episode of the second campaign of Critical Role. The Mighty Nein head for the lawless island of Darktow, engaging in an act of piracy along the way...




Previously on Critical Role

Last we left off: The Mighty Nein, after making a daring escape from the Temple of the False Serpent on the island of Urukayxl had managed to nearly drown in the escape, make their way through the jungle being chased by both yuan-ti and the lizardmen denizens of this island. Making their way to the shore just in time to have the actual pirate ship, the Squalleater, there to defend you. Firing various heavy cannon balls towards the creatures which had given chase and allowing you to escape on the boats to safety. Upon reaching the top of the ship you found that The Mistake has been repaired enough to be seaworthy, though it does need some more intense repairs.

Your supplies are relatively low, and it looks like the current is goal to find your journey westward to the island of Darktow which has been wiped-- from your knowledge-- wiped from the Clovis Concord's control many years ago and currently resides as the center of all piracy in the Lucidian Ocean.

As you all went to rest for the evening, Fjord [...] had an evening's conversation with Captain Avantika, in which it was discussed his past history with his childhood father figure, who also seemed to have a history with Avantika as well and is somehow rolled in with this strange Uk'otoa phenomenon. It also came to light that this shipwreck which gave Fjord his powers might have a connection, based on the Captain's intuition, with where this third and final sphere may lie, and it was decided between the two of them that this may be the next goal, beyond Darktow, to pursue. After which, they fucked.

Part I

Campaign 2 Tracker Map, Episode 41

Caleb gives Caduceus the Periapt of Wound Closure that had formerly belonged to Mollymauk Tealeaf, stating that because Caleb is always far back in combat anyway, it would do Caduceus much more good in the event that he goes down. Caduceus asks Caleb if he believes in fate. He goes on to express that he believes Caleb is being shaped by the world into "something important," and that he wants to ensure that he helps Caleb get to that point.

Beau asks Caleb to see if the red feather she got is magical. He does, and it isn't. Jester determines that Sprinkle is still alive, thought wet and unhappy, and then asks a reasonably drunk Nott if she's ever kissed a boy. She has, and Jester wants to know what it's like, because she's not sure if the "kiss" she got from Fjord to give her air counts. Nott thinks it does. Jester asks about Nott's first kiss-- it was just kids daring each other to kiss. Nott says she doesn't remember his name, but she remembers the softness of his lips. It was a good day. Nott advises Jester to play a little hard to get with Fjord.

The party choose ship's jobs to learn: Caleb navigation, Nott powder monkey, Fjord quartermaster, Jester carpenter, Caduceus boatswain and Beau cooper. Jester discovers Orly giving another deckhand a tattoo and is fascinated, so he teaches her. Also, for prices ranging from 2200 to 5000 gp worth of different powdered gems, he can give tattoos that give permanent +1 to stats, or fire or cold resistance.

Fan art of Nott the powder monkey, by Aviv Or.[art 1]

Roughly eight days into the journey, they spot a Clovis Concord ship, The Stormcap. Avantika says they could head it off, and asks Fjord what he thinks they should do. She says that most of the time there's no need for loss of life in a pirate encounter, just intimidation. Fjord asks Jester and Caduceus what they think, and then tells Avantika that as long as they can abstain from violence, they'll do it. Nott tries to fire a warning shot with a cannon, but blows up the first one. The second succeeds. They pull alongside and Caduceus uses Thaumaturgy to project his voice onto the other ship saying that they want to keep the encounter as bloodless and reasonable as humanly possible. Then he makes all the doors and ports on the ship open, intimidating the crew. The captain agrees to talk, and they demand food and water, gems if possible, and free access below decks to see if there's anything interesting. In return, Caduceus will heal their crew. The captain agrees, and they board, with Beau and Fjord going below.

Beau searches the captain's quarters, finding a notation about a guarded package on board. She finds a hidden small chest that sounds like it's full of coin. Fjord has the other crew move supplies over to the Squalleater, and they continue to search for the package. Meanwhile Jester demands a "volunteer" from the other ship and gives him a tattoo of a smiley line with two tusks sticking out and googly eyes. While Fjord and Beau are below searching, they are attacked by a guard, who Beau stuns. Yasha grapples him, and Fjord tells him to surrender, which he does. They recover the package he was guarding: a beautiful wooden box. The guard was to get 150 on successful delivery, so Fjord gives him 70, and Caduceus heals him. Nott is able to disarm and pick the locks on the box - it is a pot of paint and a paintbrush, both magical. Nott hides the box, and they all scurry back over to the Squalleater.


Part II

The chest from the other ship is picked and opened by the crew, and contains quite a bit of coin. Avantika says she's impressed by their work, and the Nein (except Fjord) all gather in one cabin where Caleb identifies the paint and brush they found on the other ship as Nolzur's Marvelous Pigments, which allow the creation of a 3-dimensional object by painting a 2-dimensional representation. They are given to Jester, who promptly paints a stone dick. The shield Nott previously looted from the Temple of the False Serpent is also identified as being able to "blast an enemy with a bit of arcane oomph." Caduceus keeps it for the time being.

They go get Fjord and discuss their future plans. Nott loves being a cannoneer and is fine with a life of piracy, but the others have reservations. Fjord tells them that Avantika knew Vandran, that Vandran carried the Sword of Fathoms that Fjord now has, and that Vandran also had one of the eye spheres. She believes if they search the shipwreck site, they'll find it. Fjord believes there are three spheres: one that Avantika returned to the Temple, one that he carries, and the one that Vandran held. He tells them they're going to Darktow, and they can re-evaluate there. Jester suggests Fjord seduce Avantika in an attempt to get more information.

Fjord asks to speak to Caleb privately, on deck, and tells him that he was surprised by Caleb's calculatedness in advising Fjord how to handle Avantika. Caleb responds that he learned a lot from his father about courage, that he thinks traveling with the group has emboldened him, and that he likes the group and enjoys traveling with Fjord. Fjord asks Caleb to keep an eye on Avantika, and seems to be asking Caleb to take over for him if things get out of hand. At the end of the conversation, Caleb warns Fjord via Message that he believes Avantika will try to kill him, and Fjord agrees.

One night during the voyage to Darktow, Jester is alone when she is visited by the Traveler. She asks him how to make a boy like her, but seems reluctant to use the enchantments or trickery he advises. He then suggests, "Listen to what piques his interest. And then happen to be the source when he needs it." She plans to use her paint to make many statues of the Traveler, and he suggests she place them where they would be the least expected, and the creepiest to find. He reminds her of Traveler Con, coming within a year.

Fjord has another dream from Uk'otoa, of three green lights. One resolves into Avantika, one remains on the horizon, and Fjord realizes he is the source of the third light. The three lights all plunge downward toward the ocean, into the center of a misshapen triangle formed by three large land masses. There Fjord sees a tilted tower containing a gleaming yellow eye, and hears Uk'otoa's voice say: "Reward." When he wakes, the party searches the map but can't find where it refers to.

Nott steals black pepper, thinking it is black powder, and constructs a pepper bolt.

Fan art of Darktow's Harbor, by BlackSalander.[art 2]

They reach the Dragshallow Reefs, and Fjord and Caleb recall that Darktow is now run by the Revelry, which began as a group of disgruntled shippers taking over Darktow from the Clovis Concord. Since then, Darktow has become the center of piracy in the area, and the Revelry is run by the Plank King. The ship sails up the channel through the reefs, and reaches the jagged cliffs and rocks of Darktow Island, the harbor, and the hive-like pirate city built into the base of the cliff. They dock and The Mistake pulls into the other side of the harbor. Jamedi Cosko gets his pay from Avantika and disappears into the city.

Avantika suggests they all go to the Bloated Cup for drinks, but on the way an assistant of the Plank King meets her and tells her the King wants to meet the new blood on the island. They climb precarious stairs leading up the cliff face to a cave, warm and fire-lit. Sitting on the throne is a male goliath with long black curling hair (which they later notice appears to have been "adopted" from the head of his predecessor). The Nein introduce themselves, some using aliases, and the King questions them briefly about their motives, then tells them the only law in Darktow is "No trouble between pirates on the island." He accepts a coin-filled chest from Avantika, and sends them on their way. But on the way out, the Plank King quietly comes to Beau and whispers in her ear that if Avantika ever does anything untoward, let him know and there will be some grand coin in it for her. On that, they all retire to the Bloated Cup.

Featured Characters

The Mighty Nein





  • Caduceus: Mister Caleb, do you believe in fate? There are lots of different kinds of fate, I know that's a heavy question, but do you believe that we are driven towards something by things that are greater than ourselves?
    Caleb: I don't know. I would like to think not, but I don't know.
    Caduceus: There are times that I think about the cruelties of the world and the things that have been put upon me and my family, and I would hate for that to be a plan, and there are times when, like today, I'm very grateful for being in the right place at the right time to make sure that the right people are becoming strong in ways they need to be. I don't think that excuses the pain. I don't think that you have to not care about it or fight it with everything you've got, but I think the world is shaping you into something important, and I want to make sure that you get to wherever you need to be.
    Caleb: That's a pretty big matzo ball.
    Caduceus: You won't have to work very hard at it, I imagine. I think just being you wherever the world puts you will do just fine.
  • Jester: Traveler, how do I make a boy like me?
  • Caleb: (via Message to Fjord) I think that woman is going to try to kill you, I really do.
    Fjord: Yeah. Just so. I'll turn and walk off.
  • Avantika: Well, that was harrowing and... necessary, but over! Now for drinking, yes?
    Fjord: Indeed, he seems like quite the, um, benevolent leader.
    Avantika: He's certainly a series of adjectives, yes, I'll give you that.


Adjustment Count Item Source Destination Notes
Transferred 1 Periapt of Wound Closure Caleb Widogast Caduceus Clay Caleb gave Caduceus the Periapt of Wound Closure after Caduceus had a series of near death experiences.[1]
Acquired 1 Nolzur's Marvelous Pigments Locked box on The Stormcap Nott Nott stole the box of magical pigment and brush from a ship the Nein raided.
Transferred 70 gold Fjord Soma
Transferred 1 Nolzur's Marvelous Pigments Nott/Caleb Jester After identification, Caleb gave the pigments to Jester.
Acquired 1 handful Pepper The Squalleater Nott Nott attempted to steal black powder, ending up instead with pepper.
Crafted 1 Pepper bolt Nott Nott created an "explosive" bolt with the pepper.


  • Sam's flask bears a black and white image of the Philadelphia Flyers mascot Gritty in this episode.


  1. See "A Pirate's Life for Me" (2x41) at 0:17:08.


  1. Fan art of Nott the powder monkey, by Aviv Or (source). Used with permission.
  2. Fan art of Darktow's Harbor, by BlackSalander (source). Used with permission.