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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.
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 wearing ragged clothing.
Without a doubt, Dr. Anna Ripley was one of the deadliest enemies that Vox Machina has ever faced. 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 sees 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 Percy's notes, left behind in his workshop after he fled the Briarwoods and Whitestone, as well as additional information gained by interrogating Percy after she thwarted his assassination attempt and captured him. 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.
As revealed by Matthew Mercer in "Talks Machina #49: 'Curious Beginnings'" (TMx49) and the Fireside Chat, 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.
Before the Stream Edit
A year after the Briarwoods seized Whitestone, 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. Ripley interrogated Percy, particularly interested in his curious barreled ranged weapon. After Ripley decided she had whatever useful information she could get from Percy, she and her guards left him there to die of starvation. Ripley had almost succeeded, but unbeknownst to her, 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.
Later, when her work for the Briarwoods was completed, Ripley tried to leave, but the Briarwoods threw her into a dungeon under Whitestone Castle.
"Against the Tide of Bone" (1x32) Edit
Vox Machina found Ripley in the dungeons of Whitestone Castle, disguised as an old woman who introduced herself as "Gloria Cyn".
Vox Machina begrudgingly let Ripley out of her cell.
While investigating Ripley's room at Whitestone Castle, 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.
"Return to Vasselheim" (1x43) Edit
"The Chase to Glintshore" (1x67) EditFrom Vasselheim, Ripley traveled to Ank'Harel, as Vox Machina discovered when they found evidence that a firearm had been used to kill Mistress Asharru. Keyleth examined Ripley's former pistol, now in Percy's possession, and discovered a magical enchantment, which they learned Ripley was using 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.
"Cloak and Dagger" (1x68) Edit
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 Edit
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.
Character Information Edit
Class Features Edit
- Action Surge
- Extra Attack (3 attacks per action)
- Indomitable (two times per rest)
- Second Wind 
- Martial Archetype: Gunslinger
Notable Items Edit
Animus(taken from her corpse, given to Percy)
Cabal's Ruin(taken from her corpse, given to Percy)
- "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)
- 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 "The Coming Storm" (1x73), 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.
- ↑ Dr. Ripley first appears in "Against the Tide of Bone" (1x32), under a magical disguise.
- ↑ See "Against the Tide of Bone" (1x32) at 3:17:23.
- ↑ See "Cloak and Dagger" (1x68) at 3:14:15. Ripley uses an Action Surge
- ↑ See "Cloak and Dagger" (1x68) at 2:35:13. Ripley uses a Grit point
- ↑ 5.0 5.1 5.2 5.3 CritRoleStats Monster Analysis: Dr. Anna Ripley and Company (Part 1); citation needed.
- ↑ See "Cloak and Dagger" (1x68) at 3:53:58.
- ↑ See "Cloak and Dagger" (1x68) from 4:21:53 through 4:24:20.
- ↑ See "Cloak and Dagger" (1x68) at 2:34:18.
- ↑ See "Cloak and Dagger" (1x68) at 1:27:40.
- ↑ 10.0 10.1 Matt confirms she can reload as a bonus action, Gunslinger level 15 ability.
- ↑ See "The Feast" (1x24) at 0:22:36.
- ↑ See "Against the Tide of Bone" (1x32) from 3:16:03 through 3:17:31.
- ↑ See "Cloak and Dagger" (1x68) at 2:34:40.
- ↑ See "Cloak and Dagger" (1x68) at 1:40:13.
- ↑ See "Cloak and Dagger" (1x68) at 1:37:57.
- ↑ See "The Feast" (1x24) from 0:22:32 through 0:23:27. Percy relates his first attempt to hunt down Ripley.
- ↑ See "Against the Tide of Bone" (1x32) from 03:10:53 through 03:34:05.
- ↑ See "Reunions" (1x33), part 1.
- ↑ See "Reunions" (1x33), part 1, at 0:56:06.
- ↑ See "Reunions" (1x33).
- ↑ See "Reunions" (1x33), part 2, at 0:23:39.
- ↑ See "Return to Vasselheim" (1x43).
- ↑ See "A Traveler's Gamble" (1x66).
- ↑ See "The Chase to Glintshore" (1x67).
- ↑ See "Cloak and Dagger" (1x68) at 2:16:35.
- ↑ See "Cloak and Dagger" (1x68) at 1:48:33.
- ↑ See "Cloak and Dagger" (1x68) at 3:14:15. Ripley uses Action Surge
- ↑ See "Cloak and Dagger" (1x68) at 3:32:35. Ripley uses Second Wind
- ↑ See "Cloak and Dagger" (1x68) at 2:35:52. Ripley casts Hex
- ↑ See "Cloak and Dagger" (1x68) at 3:51:40. Ripley casts Shield
- ↑ See "Cloak and Dagger" (1x68) at 2:05:45. Ripley casts Blink
- ↑ See "Cloak and Dagger" (1x68) at 3:53:20. Ripley casts Fireball
- ↑ See "Passed Through Fire" (1x69) at 0:22:33.
- ↑ See "Passed Through Fire" (1x69) at 1:47:01.
- ↑ See "Cloak and Dagger" (1x68) at 4:10:35.
- ↑ Fan art of Dr. Ripley, by fl0werb0ys (source). Used with permission.
- ↑ Fan art of Anna Ripley wearing Cabal's Ruin, by David Rodrigues (source). Used with permission.
- ↑ Fan art of Anna Ripley arriving on Glintshore, by DJ Crumrine (source). Used with permission.
- ↑ Fan art of Dr. Anna Ripley versus Percy on the Isle of Glintshore, by Truffery (source). Used with permission.