Sterling Smiles

Art by JoeFudge in artbreeder

### Main Campaign(s)

*Voidstar Act 1*, *Voidstar Act 2*, *Miss Demeanor*, *Final Battle Vs. Kaasma Khara*, *Chamber of the Eight*, *Fallen Hero Weyzi*, *The Shadow Invasion*, *The Ishtarian Job*

### Guest Appearances

*Spire of Euclid*

> *"I was more their storyteller that went along with them, actually. But yes, I... I was there. I was there the whole way. I was there when we were just fighting bandits on the road, up until we fought a great dragon, made of Void energy. I was there all the way, to defeating a Voidstar in Atlas and watching it rise into the sky, as all those around me ascended, and I did not. I was there for every damn minute of it."*-Sterling Smiles
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**Sterling Smiles** is a veteran adventurer and storyteller from long ago. He and his friends, The Fallen Heroes, overthrew the gods Div and Void 500 years ago, giving rise to the Age of Mortality in the process. Sterling was personally involved in the defeat of Void. However, when his friends ascended, Sterling successfully resisted the pull and was left behind. He wandered the dormant world for some time before returning to Gubwater Keep. With a vial of Basilisk Venom, he petrified himself there, in the hopes that one day he would awaken to see the world that would come to be.

## Description

### Appearance

Sterling has the appearance of an older gentleman with long salt and pepper hair and a beard. His face appears to be weathered with age and travel Despite his age, he possess a athletic physique. He typically dresses in simple black clothing. Due to his silver fox attributes, Sterling has garnered the attention of several individuals for his good looks.

## Personality

> *"I'll try anything once."*-Sterling Smiles
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Sterling presents himself with a sort of quiet dignity, maintaining an air of composure even in the direst of circumstances. He often acts respectfully in the presence of others as a result. He is innately good natured, seeking to support others with through both word and deed with little hesitation. He is a good listener and equally good at understanding people. Notable instances of this included seeing through the disguise of Dmitrius Valiensworth and identifying the emotional turmoil present in Captain Layton.

Sterling often advocates for diplomacy and compromise when faced with adversity. He looks to violence as a last resort and prefers to talk things out and understand his opponents. His natural charm aids him in this, such as when defusing the tense situation between the crew of the Miss Demeanor and the Inevitable before things got out of hand. This trait ensures Sterling always exercises caution when approaching a dangerous situation. An expectation to this rule appears to be Bronn, who he shares a mutual animosity with.

An interesting quirk of Sterling's is his humility, especially when it comes to his time with the Fallen Heroes. He rejects the title of hero, seeing himself more as a storyteller who followed them around. He often avoided speaking of them and redirecting the conversation, flat out denying his involvement on one occasion when the Hunters he aided noticed an engraving of the Heroes with him also present. Only when he is in trusted company or if the situation demands it does he drop this pretense, acknowledging his role in their story. For all his evasion regarding the Heroes, he very clearly cares deeply for them, especially for Weyzi, who brought him back from the brink of depression and helped him deal with his alcohol addition.

However, all this does not mean Sterling is without his silly side. He is more than capable of cracking jokes and performing ridiculous songs, even in the middle of combat. His childish insistence that his group of Fallen Heroes were superior to the other half of the pantheon is another example of this. He can also be prone to spontaneously reckless moments, such as when he ate a berry from a mysterious bush and got a temporary third eye for his troubles. Despite these moments, Sterling is always considered to be reliable, dependable and trustworthy in any situation.

## History

### Background

#### The Unscattered Bard

Though not a member of the Pantheon, a writer and Bard named Sterling Smiles has been recorded as travelling the world, leaving stories, books, and songs across Io telling tales of the  Heroes and the Dead Gods. Many people are unsure of their legitimacy, having no record of this man beyond his own written word. Despite this, hobbyists and historians have pieced together recorded memories and visions from the Pantheon and confirmed much of the information stays true despite being hundreds of years old.

If his writings are to be believed, he was a Hero alongside the Pantheon, who saw the Death of Void and lived, by luck or divine fate. Though his work is a boon to those who consider it truth, it is occasionally tainted with loneliness and a bitter hatred to have survived when the other Heroes did not. His work seems to have spanned a period of 40-50 years, marking the supposed end of his natural life.

## Phase 2 Story

### Discovery at Gubwater Keep

Seeking a means to fight the evil Warmaster, the crew of the Miss Demeanor travelled to Gubwater Keep at the suggestion of Laurence Sidsworth. The fort was the one-time headquarters of the Fallen Heroes and the pirates anticipated it may possess powerful artefacts. While they were looting, Alice and Layton came upon a statue of a man upon a stage, along with an empty vial containing traces of Basilisk Venom and a song. The song inferred that the statue was once a man who had fought Div and Void and petrified himself not long after. The song requests that a spell of Greater Restoration may be used upon the statue to restore the person it once was. The pirates decide to pursue his request at a later date, and initially leave the statue behind. However, a Void maw opens up near the keep, threatening to swallow it whole. Layton rushes inside to save the statue and the party agree to bring it with them.

### In the Hands of Ironside

The crew follows the sword Immortal to the Lost City of Krakesque, where they run aground due to a raging tempest. Upon learning of the requirements to enter Krakesque by a kobold, they request that he return the ship back to Kreshart along with the statute. The kobold obliges, and the ship is teleported back along with a member of the crew, Wood Gnome. However, Kreshart had been annexed by the infamous Captain Ironside. Wood Gnome, afraid for his life, surrendered the ship and statue to Ironside. Ironside, a well travelled individual, understood the importance of the statue, though it is unclear he knew who it once was. He took the statue with him to the old fort he took over, and kept it there as he busied himself with exerting control over the once free city.

### A Hero Awakens

A month later, Ironside is forced to defend against a rebellion from the citizens of Kreshart, spearheaded by an Orc called Ushwin and the crew of the Miss Demeanor. The pirates fight their way to the old keep and fight Ironside to the death. During this, a Void Seed within Ironside takes over as the pirate lord dies, and his animated corpse fills the room with Void energy. The statue appears to react to this, cracking in several places. Once Ironside is thoroughly dispatched, the crew check on the statue, which then crumbles, revealing an older man within; Sterling Smiles. The crew of the Miss Demeanor explain the situation to him, and he agrees to join them for the moment. Sterling is particularly taken aback by the young sorcerer Alice, which whom he gets a sense of deja vu. On the journey back, Sterling gets to know more about his rescuers. He talks with the boy about their potential connection, with Alice inquiring about Sterling's history in turn. Sterling learns of how his friends were remembered through visions and emotions scattered across multiple people. He also learns the current year is 735, 477 years after he was petrified. Sterling admits to Alice that he was there when the gods died, but remains vague about the details. Sterling engages in conversation with Layton and Armstrong soon after, where he is offered a place on the Miss Demeanor. Sterling agrees to join them on their adventures, one of which includes a apocalyptic threat to Io.

### Part of the Crew

Once back in Kreshart, Sterling is present when the crew are approached by the caretaker of the Astral Academy, Rorn. He warns them of the betrayal of the goblins which have identified Captain Armstrong as a target of Kaasma. He also informs them of a Void dragon that needs to be studied. Sterling recognizes the description of the dragon, having once fought one before. Sterling later joins in on the celebrations, playing a fiddle for the people of Kreshart to dance to. During the festivities, he is taken to one side by the pirates that rescued him. Captain Armstrong informs them that an individual approached him, declaring he had been awakened by his deity Kaasma and tasked with killing Armstrong. Though missing much of the context, Sterling nonetheless agrees to help Armstrong deal with this potential threat.

Sterling joins the others in the morning as they set out into open water aboard the Miss Demeanor, with the self-proclaimed assassin. Once far enough from shore, the man transforms into a hideous beast and attacks. Sterling aids the pirates by animating objects, inspiring the defenders and casting all manner of magics. Though the creature received backup, Sterling and his new allies defeat both creatures. Upon their demise, the crew, including Sterling, receive a series of disturbing images of strange lands and a metal facility. Sterling theorizes that seeing such images was the creature's attempt to reach out to its home, and they were not meant to witness it. After leaving to write it all down, a wild magic phenomenon triggered by Alice summons hundreds of books onto the ship. Rescuing Layton, who fell overboard as a result, the two go to dispose of the body. Sterling tries to extract the brain to try extract memories, but botches the attempt.

Afterwards, Sterling witnesses Layton using his sword to absorb the soul of their assailant before they toss him overboard. Having once been possessed by a cursed sword, Sterling warns Layton about the potential of losing himself to its influence, something that greatly upsets the captain. He also brings his concerns to Captain Armstrong as well. After some consoling from the other crewmates, Sterling apologies to Layton for being too blunt, which the troubled captain accepts. Not long after, Sterling goes for a nap as the ship travels back to Kreshart. However, his sleep is interrupted by a dream of the battle with Void, where he relives being left behind by his friends.

### Negotiating with the Inevitable

The Miss Demeanor returns to Armstrong's home, where a portal to the Astral Academy is being manned by constructs. Alice proposes that they seek the aid of the Exodus Academy to try and defeat Kaasma Khara and sever the connection between Skrum and the Deep One. This means travelling across the dangerous permanent storm pattern known as the Serpent's Smile. Thus they decided to go to the Astral Academy to seek help in this endeavor. Sterling, absent-mindedly scribbling away, agrees to join. The pirates go before the Inevitable, requesting its aid in upgrading the Miss Demeanor. The Inevitable, having previously tasked them with taking on the Void Dragon, becomes more and more irate at the pirates and refuses. Eventually, a throwaway line from Layton about looking to Kaasma for help triggers the Inevitable, causing him to become hostile. Sterling manages to step in and calm the Inevitable. He asks for a compromise, seeing if the construct wanted anything done on the continent of Ishtar. The Inevitable admits that it does; the head of the Headmaster of the Exodus Academy. Though secretly Sterling intends to offer no such thing, he agrees, and the Inevitable sends constructs to improve the Miss Demeanor for its journey. During their wait, Sterling asks Armstrong to share the stories of the Miss Demeanor and its captain with the intention of writing a memoir.

### The Serpent's Smile

After some time, the upgrades to the Miss Demeanor are completed, with a new reinforced hull and a steam-powered engine. The crew sets sail towards Ishtar, and the trip goes relatively smoothly for the first part. However, upon entering the Serpent's Smile, the voyage becomes extremely perilous, with ferocious winds and swells threatening them at every turn. Sterling proves to be an invaluable ally when crossing the Smile. While not experienced in sailing, it is in dealing with the more fantastical elements of the Smile that the Unscattered Bard really excelled. On the second day in the Smile, Sterling saves Alice from falling off the ship by animating a rope to help keep him from going overboard. Not long afterwards, the ship collides with the source of the storm pattern; an ancient Kraken. While Sterling's attempt to polymorph it failed, his animated rope manages to stabilize Alice in steering the ship away from the creature. Sterling also bottles up some of the Kraken's poisonous ink after they manage to escape it. The following day, Sterling manages to persuade a Lighting Elemental to leave them in peace, saving the group from a hazardous combat. A day later, Sterling decided to polymorph into a giant ape to aid in manning the sails. During this day, the legendary Sea Witch of the Serpent's Smile clambers aboard. Her menacing visage causes fear in all who see her, including Sterling. The hag then tried to stop the heart of Captain Layton to try and take them overboard. When Khairen rescues him, the hag loses her temper and begins to maul Khairen to death. Overcoming his fear just in time, the polymorphed bard wrestles the hag, causing her to drop Kharien, and tosses her into the tumultuous ocean. Once the hag is left behind, Sterling reverts to human form and heals Khairen, stabilizing her.

After such a harrowing experience, the crew takes some time to gather themselves and share some chocolate. Sterling continues to help Alice with the sails. The next day, Armstrong spots an uncharted island in the midst of the storm and declares his intent to explore it before moving on. Though the decision divides the crew, Sterling advocates for the adventure, though he stresses caution. The ship arrives at the island, which appears to be completely uninhabited. While there, the crew find a dense jungle and come across some strange berries. Sterling, in a moment of spontaneity, eats a berry and begins convulsing in pain. After a few moments, a third eye appears on his head, similar to one of the common effect of wild magic. While this causes concern from the party, it is overshadowed by an unsightly gigantic beast moving through the jungle towards them. The crew flees back to the ship and they cast off once more. Sterling's new eye disappears shortly afterwards. Later that night, Luna recieves a telepathic contact from her cousin, Mayliera. Her cousin admitted to trying to summon Kaasma Khara to Io, to try and harness its power. She also warned her not to come to the Old Academy and berated her for abandoning her people. This left Luna emotionally distraught, during which her friends comforted her and discussed what she had learned. Sterling propositioned that even if they were the last defenders against this threat, they should still fight. He ensure Luna that Mayliera may be blinded by power, but may yet be saved. With those encouraging words, the pirates make their way to the Old Academy to put a stop to the ritual, leaving the Serpent's Smile behind.

## Mechanics

### Powers and Abilities

* **Immortality**: The fight with Void left Sterling forever changed. Though he was previously unaware of it, Sterling is in fact immortal, and cannot die of old age. However, this does not make him invulnerable.

#### Bard Abilities

* *Bardic Inspiration (D10)*
* *Jack of All Trades*
* *Song of Rest (D10)*
* *Expertise*
* *Font of Inspiration*
* *Countercharm*
* *Magical Secrets*
* Creation Abilities
	+ *Mote of Potential*
	+ *Performance of Creation*
	+ *Animating Performance*
	+ *Creative Crescendo*

#### Feats

* *Resilient (Con)*
* *Skill Expert*

#### Spell list

##### Cantrips

* *Light*
* *Minor Illusion*
* *Prestidigitation*
* *Vicious Mockery*

##### 1st Level

* *Dissonant Whispers*
* *Faerie Fire*
* *Healing Word*
* *Tasha's Hideous Laughter*

##### 2nd Level

* *Heat Metal*
* *Shatter*
* *Suggestion*

##### 3rd Level

* *Counterspell*
* *Fear*

##### 4th Level

* *Dimension Door*
* *Polymorph*

##### 5th Level

* *Circle of Power*
* *Hold Monster*
* *Mass Cure Wounds*

##### 6th Level

* *~~Heroes' Feast~~*
* *Otto's Irresistible Dance*

##### 7th Level

* *Mordenkainen's Magnificent Mansion*
* *Simulacrum*
* *Teleport*

## Trivia

* Sterling is the first character in a streamed campaign to get past level 10 in their respective class. This also makes Sterling the first official Mentor character in Io, allowing him to teach other Bards higher level skills.
* Sterling rolled a natural 20 on his Constitution Saving Throw when the Heroes ascended. This met the DC of the save and allowed him to resist ascending with the others.
* Sterling appears as an enemy in the fight against the Altered Void. In this reality, Sterling and his friends failed to defeat Void and Io was destroyed.
* Sterling once had a butler named Toby, who eventually became Bronn's squire.
* Sterling's Simulacrum is named Smerling Stiles.

## Images

### Official Art

Sterling Smiles as he appeared in Voidstar Act 1Sterling Smiles as he appeared in Voidstar Act 2A VOID corrupted Sterling Smiles enslaved by the Altered VOID.