Sylas Briarwood

Lord Sylas Briarwood was the vampire co-ruler, along with Lady Delilah Briarwood, of Whitestone and other lands to the north after usurping the de Rolo family. Sylas and his wife were in the service of Vecna.

In both Critical Role and The Legend of Vox Machina, Sylas is played by Matthew Mercer.

Appearance
Sylas was a strong, tall man, with short brown hair framing his chiseled and handsome face, which was adorned with a well-groomed goatee. When Vox Machina first met him, Sylas's clothing was predominantly blue and black with gold and red trim. He wore a strip of gray fur cresting over one shoulder and framing his torso.

Personality
Sylas is loyal, practical, and has a supernatural charisma. He is also sinister and cruel with very little empathy for those who are not Delilah or himself. However, he does genuinely care for his wife, willing to do anything to defend her and usually deferring to her wishes.

Background
The Briarwoods had enough powerful connections to maintain a comfortable life in the Dwendalian Empire. At some point, Sylas became sick with a disease that no one could seem to cure. Delilah Briarwood set out to find something or someone who could help her husband, and though she did succeed in this quest, she returned too late and found that Sylas had already passed. Delilah agreed to serve Vecna in return for him to help Delilah perform the Rites of vampirism, binding Sylas to Vecna and raising Sylas as a vampire.

When Delilah's necromancy and Sylas' undead nature were found out, they were ousted from the empire and fled to Port Damali, where they met Anna Ripley. When they heard about an isolated city called Whitestone, they dubbed themselves 'lord and lady' and visited Whitestone from Port Damali, building a relationship with the de Rolo family.

During the occupation of Whitestone, Sylas had his Charms that forced many of the city's denizens to submit against their will, according to Cassandra de Rolo, the Charm did not work on her, because of her deep hatred. Two years after the occupation, Lord Briarwood, knowing of the rebellion's plans to infiltrate the Whitestone Castle, waited for them in the forest and slaughtered most of the rebels, but he recognized Cassadra among them, sparing her.

At the end of a meeting with the Tal'Dorei Council, Percy asked Sovereign Uriel about the Briarwoods' visit to Emon. Uriel told Percy that the Briarwoods were interested in establishing an official trade route from Whitestone to Emon, using their fabricated story that the de Rolo family gifted Whitestone to the Briarwoods before the family died. Percy asked to be notified when the Briarwoods returned to Emon, and withheld the truth about the Briarwoods' attack on the de Rolos from the sovereign.

Seeker Asum Emring visited Greyskull Keep to inform Vox Machina that the venture, helmed by the Briarwoods, to build a bridge over the Shearing Channel had been agreed upon. The bridge would connect Tal'Dorei to the continent of Wildemount, set at the edge of the Alabaster Sierras. Asum questioned why Percy was uncomfortable at the mention of the Briarwoods, and Percy told him that he found them untrustworthy. Asum agreed with Percy's assessment, as he had sent operatives into Whitestone, only to have them resign. Vox Machina agreed to attend the dinner.

Sylas and his wife visited Emon as part of a campaign to build a bridge across the Shearing Channel to Wildemount. Sovereign Uriel threw a feast in their honor, where they were introduced to the members of Vox Machina. At the feast, Sylas discussed the merits of a trade route to Wildemount and engaged, along with Delilah, in conversations with Vox Machina. Afterward, Vax tracked the couple to their guest room and tried to sneak in. Vax was caught at the door, and Sylas helped drag him into the room.

When Sylas failed to charm Vax, the couple moved to attack him. Delilah deals necrotic damage to Vax, while Sylas bit him, revealing his vampirism. Vax attempted to escape by jumping out of a window, and used his Earring of Whisper to alert the rest of Vox Machina.

Vox Machina then joined the fight against the Briarwoods, with new ally Lilith to help, while Sylas charmed Seeker Assum. When Percy hit Sylas with multiple shots, a frustrated Sylas pulled out a previously invisible slate-gray greatsword. After Sylas had sustained a lot of damage, Delilah cast Dimension Door away from the part.

After the fight with the Briarwoods, Vox Machina attended a council meeting to explain their actions. Although the party explained the Briarwoods' true history with Whitestone and Sylas' vampirism, it became clear that Uriel had at some point been charmed by Sylas. Believing Vox Machina were the true instigators of the attack, Uriel removed the party from the council pending further investigation.

Vox Machina then interrogated Desmond, the Briarwoods' carriage driver. Desmond told the party about the Briarwoods' invasion of Whitestone, and the harsh life under the Briarwoods' rule. He told them that all of the servants in the castle were undead, and that the Briarwoods spent a lot of time excavating something underneath the castle.

When the party became trapped in an acid distillery, both the Briarwoods' appeared, and Cassandra revealed that she had aligned herself with the couple. When Vax separated from the party, Sylas successfully charmed him. The party escaped the acid trap and followed the Briarwoods, along with a charmed Vax, into the ziggurat.

A fight started in the ziggurat, Sylas appeared most affected by the radiant damage caused by Keyleth's Sunbeam spell. Angered by Percy attacking Delilah, Sylas willingly stood in direct sunlight to attack Percy in revenge. After suffering more radiant damage, Sylas was shot in the chest by Percy, dropping him to zero hit points. This turned Sylas into his mist form, which Keyleth destroyed using Sunbeam.

Sylas is seen with his wife Delilah atop a bone dragon, returned to life (or undeath) by Vecna at some point after his ascension.

Upon Vox Machina's destruction of part of the barrier protecting Thar Amphala, Sylas and Delilah rode in on their undead dragon to investigate. After Delilah's death, Sylas fled in bat and then mist form, moving quickly enough to avoid death by a sunlight generating spell. As a vampire reduced to 0 hit points, Sylas was forced to return to his resting place and be paralyzed for an hour before regaining any hit points.

Sylas was last seen through Keyleth's scrying. Still in bat form, he was flying frantically through the Vesper Timberland to escape.

A year after Vecna's defeat, Sylas and seven of his vampire minions attacked the wedding of Percival and Vex'ahlia de Rolo at Dalen's Closet. He drugged the wine at the rehearsal, knocking out the majority of the party and abducting Percy and Vex. He bound them in chains and threw them off a cliff into the ocean below. As Vox Machina and their allies closed in, he attempted to flee but was killed by Vex before he could escape and his mist form was destroyed for good by the sunlight she radiated as the champion of The Dawnfather.

Delilah Briarwood
Sylas was married to Delilah. He was deeply devoted and loyal to Delilah, waiting until Percy and Vex's wedding to attack and kill the couple for killing his wife.

Notable items

 * Brooch of Living Essence
 * Greataxe of the Eclipse (requires a Wisdom save if hits or deals necrotic damage)
 * Craven Edge, taken by Grog after his death in Whitestone

Abilities

 * Charm
 * Legendary Resistances
 * Legendary Actions:
 * Move - free movement without attacks of opportunity
 * Misty Escape
 * Multiattack:
 * Bite
 * Claw Attack

Appearances and mentions

 * Campaign 1
 * One-shots
 * Campaign 3
 * The Legend of Vox Machina
 * One-shots
 * Campaign 3
 * The Legend of Vox Machina
 * One-shots
 * Campaign 3
 * The Legend of Vox Machina
 * One-shots
 * Campaign 3
 * The Legend of Vox Machina
 * One-shots
 * Campaign 3
 * 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
 * The Legend of Vox Machina

Quotations

 * "Don't worry. You look delicious." (Sylas to Vax, revealing his vampiric nature.)
 * "Would you look at that, dear? The pup yet lives." (Sylas to Delilah, when he saw Percy.)
 * "Long have I waited, learning, reading, listening, suffering. By the grace of ancient shadows stirred by a love unending, my soul was scattered beyond life and brought back twice now. Longed to be with my beloved Delilah. Twice, she sacrificed everything for me. Everything. And twice you have torn her away from me, left without hope, agony unending for this eternal life. Unlife. I am cursed now without my partner. The paltry affections you both hold for each other, mean nothing by comparison to what we had. Though, amusing it is to see you go through the motions. You do not, can not, understand what true timeless love is. You could never discover the joy that you robbed of us. For this timeless torture you've banished my soul to, I bring judgement to you both. The first of many vengeances to be brought down upon your loved ones." (Sylas to Percy and Vex after drugging and abducting them.)
 * Sylas: "I'm sorry it took this long to finish the last of the de Rolos. But it'll be nice to not worry about an incomplete position." (Vex headbutts him.) "It's almost sad it's over. I've been thinking about this moment for so long, I planned so many elaborate ways to torture you and tear you apart and—" Vex: "Tell us about them." Sylas: "I've come to enjoy the simplicity of things." (Sylas to Percy and Vex before throwing them off a cliff.)

Trivia

 * Travis Willingham was dressed as Lord Briarwood during, which aired the week before Halloween 2016.
 * In the Critical Role Major Arcana Tarot Card Set, he along with his wife, Delilah, represent VI - The Lovers.
 * Because of their necromantic nature, the Briarwoods have each been killed multiple times.
 * However, both of their final deaths come from Vex'ahlia. She killed Delilah during Vecna's siege in and both killed and fully destroyed Sylas after his assault on her wedding in.
 * Matt Mercer reprises his role as Lord Briarwood in The Legend of Vox Machina.