Anna Ripley

Dr. Anna Ripley was a follower of the Briarwoods. After the Briarwoods seized control of Whitestone, Percy attempted to kill Dr. Ripley in Stilben, but he was captured by her guards, tortured, and interrogated. Dr. Ripley began gathering intelligence about Percy's weapons and experimenting with firearm construction, losing a hand during one of her experiments. As an NPC, Dr. Ripley was played by Matthew Mercer.

Appearance
When Vox Machina first met Ripley in the dungeon beneath Whitestone Castle, she was disguised as an old woman, looking to be in her seventies. She had very deep, sunken wrinkles, weathered skin, mostly whitish-gray hair with a bit of remaining red and brown, and was wearing ragged clothing.

When the magic disguising her was dispelled, she was revealed to be a woman in her early mid-forties, with jet black hair pulled into a tight ponytail. She was wearing nice travel clothes with a long duster-like coat. Her right hand was missing. Her face was a little weathered from travel and she had dark lines at the sides of her face, whether from smiles or frowning.

Later, when Vox Machina caught up with Ripley's party on Glintshore, she was wearing Cabal's Ruin. Her dark brown hair with streaks of white was pulled into a very tight bun in the back, and familiar-looking weapons dangled from her belt.

Personality
Dr. Anna Ripley was one of the deadliest enemies that Vox Machina had ever faced, as shown when she succeeded in killing Percy on Glintshore. In many ways, she was both identical to, and opposite from Percy: both were loyal to their allies and vicious to their perceived enemies. One of their biggest differences was that Percy saw firearms and other such technology as a tool for revenge, a means to an end. Ripley viewed Percy's inventions almost as an end in and of itself.

Ripley was obsessively fascinated with Percy and his inventions. She was simultaneously admiring and envious of Percy's genius. She showed the capability to read and comprehend complex mechanical designs, as she was able to create her own firearm based on eyewitness accounts of Percy's exploits. In addition to being able to construct Percy's concepts, she showed the ability to improve upon those designs as well. For example, she was able to use her knowledge of "The List" to create the far more advanced "Animus".

Ripley was an amoral opportunist, siding with the Briarwoods and their Vecna-worshipping cult not out of faith in the god, but because she saw an opportunity to continue her research with more resources. She reasoned that the technological achievements that result from a decision are what determine whether or not something should be done (rather than a more humanistic "right vs. wrong"). She had no interest in getting involved in the struggle against the Chroma Conclave, citing that the "petty tyranny of drakes and dragons" have always fallen to "the ingenuity of Man". She also was an unapologetic racist, believing that humans were the only race capable of finding solutions to new problems and that non-humans lacked the same "dynamic ability to adapt". Thus, she genuinely believed that Vox Machina's success was only due to Percy's intelligence and ingenuity.

Ripley proved herself to be quite charismatic, as she was able to assemble her own group of followers (including Kynan Leore) as her own twisted version of Vox Machina. Unlike the real Vox Machina (whom Percy regards as family), Ripley treated her group more like tools: useful, and not to be carelessly discarded, but tools nonetheless.

Before the Stream
Dr. Anna Ripley was originally working for the Dwendalian government, developing military technology in Rexxentrum (the Dwendalian capital). However, she was caught doing illegal human experimentation, attempting to use arcane diseases as the basis for new biological and chemical weapons. Before she could be court-martialed, she fled to Port Damali, where she first met Sylas and Delilah Briarwood. The Briarwoods had been arrested for necromancy, had escaped prison, and now were fleeing hunters with orders to execute on sight. The three fugitives decided to work together, and Ripley aided the Briarwoods with their plan to murder the de Rolo family and seize control of Whitestone. Shortly after, Ripley interrogated Percy, particularly interested in details about Whitestone Castle.

During the Briarwoods' rule of the Whitestone, Dr. Ripley helped them reestablish social control. She also was one of their chief scientific designers, who worked with the Briarwoods to create an acidic compound that would distill whitestone ore into pure residuum.

A year after the Briarwoods seized Whitestone, the now-free Percival (one of the last surviving de Rolos) managed to track Dr. Ripley's location. His attempt to murder Ripley failed, and Percy was seized by Ripley's guards and thrown into a prison cell in the Umbra Hills. Her guards left him there to die of starvation. Unbeknownst to Ripley, the party of adventurers known as "Vox Machina" managed to find Percy in his prison cell, just in time to provide proper care and food.

Slightly over a week before Vox Machina arrived, Anna Ripley completed her work for the Briarwoods and attempted to leave. As Anna was packing up her belongings, Byron Anders saw this and immediately whispered about it to the Briarwoods. They threw her into a dungeon under Whitestone Castle, which Dr. Ripley believed to be a temporary measure until the completion of the ziggurat.

—
Vox Machina found Anna Ripley in Whitestone castle down in the dungeon. She was disguised as an old-looking lady named Gloria Cyn. The story she told the party was: "Gloria" came up from Drynna to ask Briarwoods — why the waters are growing brackish, and fish are dying out? Delilah laughed and threw her in the dungeon. Her main intention was to escape her cell, and Anna repeatedly asked for their help. Although once they met her, Vox Machina was inclined to accept, with each time she asked, the group felt more suspicious.

Eventually, they decided to leave "Gloria Cyn" until safe times when the Briarwoods would be no more. As a compromise, Vex started to fake picking the lock with help from the old lady on the other side of the cell. Anna visibly used both of her hands, but Vex distinctly felt only one of them. Remembering the description of Dr. Ripley, Vex'ahlia broke the lockpick and jammed the lock. Keyleth dispelled magic, revealing a black-haired woman a little over the age of forty, wearing travel clothes and a slightly ragged duster coat. Percy steped out of the shadows, wearing a Hat of Disguise, changed into a Whitestone peasant. He offered her a deal: if she led them toward their goal, she would be allowed to leave Whitestone unarmed, but with a promise that Percy would find her again someday.

Reaching an agreement, Ripley led them to her room, where Percy found many sketches of his pepperbox firearm, the List, drawn from eye-witness accounts. Ripley had designed her own firearm, a pistol similar to Percy's pepperbox but more technically refined and less aesthetically styled. It had only one barrel and a small, rotating, four-cylinder chamber.

Anna Ripley was able to escape the castle while Vox Machina was distracted by Professor Anders.

Returning to Vasselheim after liberating Whitestone, Percy learned that Victor had done business with a nicely dressed lady several weeks prior, most likely Ripley.

From Vasselheim, Ripley traveled to Ank'Harel, as Vox Machina discovered when they found evidence that a firearm had been used to kill Mistress Asharru. Both Keyleth and Kyme, a member of the Omnival Library examined Ripley's former pistol, now in Percy's possession, and discovered a magical enchantment, which they learned Ripley used to listen to them. Scrying on her, Keyleth discovered that Ripley did have Cabal's Ruin and was on a ship in the Ozmit Sea, most likely looking for Whisper, another Vestige of the Divergence.

Vox Machina caught up with Ripley in the jungle of Glintshore after she had already procured Whisper. There, they learned she had allied herself with Orthax in a similar deal to the one Percy once made.

Ripley revealed that she had no interest in becoming involved in the struggle against the Chroma Conclave, stating that the "petty tyranny of drakes and dragons" have always fallen to "the ingenuity of Man". She told Percy that after leaving Whitestone, she had continued her design and construction of firearms, and even gave the plans to other tinkerers as well as selling some firearms.

Percy was incapacitated twice during the fight with Ripley and her men but was healed both times by members of Vox Machina. Finally, Orthax appeared to aid Ripley, and with his help, she was able to take the killing shot. She then attempted to flee but was captured and brutally executed by the remaining members of Vox Machina.

Percival de Rolo III
Dr. Ripley was perhaps the only person that Percy was truly afraid of. She was the one who tortured him endlessly when the Briarwoods attacked and took over the castle. Moreover, upon learning of Percy's inventions, she became obsessed with his work and desired to replicate it. She eventually succeeded, albeit at the cost of her right hand. Their next (and last) meeting occurred on Glintshore, where she was revealed to have made a pact with the shadow demon that Percy once made a pact with, and that deadly partnership eventually led to Percy's death at their hands.

Orthax
Upon encountering Orthax, Ripley assumed the shadow demon to be the source of Percy's invention. She became fascinated with firearms and saw a lot of uses for this new technology. She was immediately curious about what secrets it might have withheld from Percy. She believed if she embraced the entity, she could learn more than Percy because she could sacrifice more than Percy's moral code would allow him to. Her pursuit of that knowledge drove her mad.

King Bertrand Dwendal
Before Dwendal discovered Ripley's experiments into biological/chemical warfare, there was bad blood between the King and Ripley. Thus, his name was listed on Ripley's gun Animus, as a target for vengeance.

Fighter abilities

 * Action Surge
 * Extra Attack (3 attacks per action)
 * Indomitable (two times per rest)
 * Second Wind
 * Martial Archetype: Gunslinger
 * Grit points
 * Lightning Reload

1st-level

 * Hex
 * Shield
 * Disguise Self

3rd-level

 * Fireball
 * Blink

Notable Items

 * Animus (taken from her corpse, given to Percy)
 * Cabal's Ruin (taken from her corpse, given to Percy)
 * Retort

Quotations

 * "I sold a couple in Vasselheim, and a few more in Ank'Harel. Partially because I needed the money, but also because...he told me it would drive you mad." (Ripley revealing her proliferation of firearms)
 * "Another name...off the list..." (just before killing Percy on Glintshore)

Appearances and mentions on Critical Role

 * Vox Machina Origins III 4 - unnamed mention
 * Campaign One: Vox Machina
 * The Legend of Vox Machina
 * The Legend of Vox Machina
 * The Legend of Vox Machina
 * The Legend of Vox Machina
 * The Legend of Vox Machina
 * The Legend of Vox Machina

Trivia

 * Matthew Mercer stated during the Fireside Chat that the main inspiration for Ripley was Nazi propaganda minister Joseph Goebbels, as both served militaristic and totalitarian governments. Goebbels was also one of the chief architects of Nazi Germany's Final Solution and the Holocaust.
 * Dr. Ripley was the first character featured in Critical Role missing a hand, followed by Cerkonos, Tyriok Gadsworth, Shale, and Victor.
 * Marisha Ray was dressed as Anna Ripley during, which aired the week before Halloween 2016.
 * Several parallels can be made between Ripley and Avantika. Each of them has a particularly antagonistic relationship with a certain member of the party (in this case, Percy and Fjord respectively); they both forged pacts with the same patrons (again, Orthax and Uk'otoa  respectively). However, a key difference between the two is that while Ripley had a whole episode devoted to fighting her, Avantika's true strength remains unknown as her fight with The Mighty Nein was interrupted by the guards of Darktow Isle and subsequent execution.
 * This changed in, in which a large portion of the episode was dedicated to fighting the undead form of Avantika when she returned to take the Cloven Crystal from Fjord.