cicero skyrim

Cicero Skyrim Guide: Skyrim’s Crazed Jester

As you journey through the rolling hills and vast open plains of Skyrim, you will encounter many NPCs that stick with you. Some of them for good reasons, and others for their tendency to either stab you in the back or ramble on drearily about something you simply could care less about. 

Throughout my hundreds of hours of Skyrim, I have probably met every one of these memorable NPCs, each taking up a precious piece of my memory, taking the space away from something useful I could remember. Of course, knowing your bank details is quite a lot more boring than remembering all the names Sam Guinevere goes by in TES. 

With all this being said, there is one NPC or side character throughout the entirety of Skyrim that really sticks out in my memory and of those who managed to stick with the game long enough to explore the Dark Brotherhood side quests.

I am, of course, talking about Cicero, the titular character and subject of this guide. The crazy jester who makes the Dragonborn and his guild companions live a nightmare for the short time he resides in the Falkreath sanctuary. 

However, one thing I like about Cicero is the depth of his character; the writers of Skyrim really did put in the time with him, ensuring he was not a simple throwaway character that would serve to annoy the Dragonborn for a short time. In this respect, as soon as I met Cicero, the first thing that came to mind was the Adoring Fan of Oblivion infamy. 

Thankfully, for the purpose of this article and our enjoyment of Skyrim, Cicero is much more than that, as he probably has one of the best backgrounds given to any side character in the game. Don’t believe me? Well, let’s take a deeper look and see if you still feel the same at the end of the article. Let’s go!

cicero skyrim
Missable Skyrim Quest Makes Dark Brotherhood’s Cicero So Much Worse

In the Beginning

Cicero’s story is a complicated one, filled with twists and turns. Due to this and the clandestine nature of his chosen profession, we know very little about the jester outside of his journal entries that we come across during the later stages of Skyrim’s Dark Brotherhood quest line.  

Assassin of Bruma

What we do know about Cicero is that he is Imperial and, therefore, was most likely born in Cyrodill, spending most of his young life there. Cicero was born somewhere between 4E 170 and 4E 176, officially joining the Dark Brotherhood in 4E 180 as a mere child of either ten or four years old.

He was subsequently raised in the Dark Brotherhood, becoming a loyal and dedicated member of the guild, learning the art of killing as other children learned to read and write.

Initially, Cicero served as a member of the Bruma arm of the Brotherhood, calling the sanctuary his home for several years. During this period, we know that he got by pretty well, completing contracts effectively and keeping to the five tenets.

However, his time in Bruma would come to an abrupt end when the sanctuary was destroyed and all members, save for Cicero, were put to the sword by the angry townsfolk on the 8th of Evening Star, 4E 186. 

assassin of bruma
Bruma, hidden in snow”.. Screenshot from TES IV Cinematic “The Beauty of Oblivion”

Moving On

Although Cicero managed to escape Bruma with his life intact, he had lost everything he had ever known or loved in one fell swoop, making him an orphan, an outcast. This was when he received an offer/order from the controlling body of the Brotherhood, the Black Hand, specifically, a member of the Cheydinhal sanctuary, Rasha. 

When Cicero arrived in Cheydinhal, the members of his new sanctuary welcomed him with open arms, sharing their love, compassion, and contracts with him. This was probably out of respect for the family he had lost in Bruma. 

As Cicero spent more time in this sanctuary, he mentioned in his journals that shades haunted the sanctuary. These shades, the trapped souls of those killed during the cleansing of the Cheydinhal sanctuary by the Hero of Kvatch back in 3E 433, affected the jester in some profound way, helping him feel more at home in his new surroundings. 

Anybody else love Cheydinhal? I mean yes it’s a wretched hive of scum and villainy – But it sure is pretty

Showing Promise

It was long before Cicero became one of the most efficient members of the Cheydinhal sanctuary, taking on a large number of contracts thanks to his love of the kill and the lack of any real competition within the guild. While we do not know the details of all of these contracts, we do know that he completed them with great skill, developing a certain cloak-and-dagger style that would become his trademark within the guild.

More often than not, he would also complete these contracts expertly, receiving both the standard reward and a bonus for the means by which he achieved said deed. 

The Baroness and the Handmaiden

More than a year into his service at the Cheydinhal sanctuary, we read in Cicero’s journal about one particular contract and the issues that occurred during the mission.

The contract, from the outset, was one of his more difficult missions, requiring the small jester to infiltrate the estate of a Baroness without being seen, murder the lady in question, and escape again. Of course, this was all within Cicero’s capabilities, but you cannot account for everything regardless of how good you are.

Speaking on this contract on the 1st of Rain’s Hand, 4E 187, Cicero notes that the contract went off without a hitch until one of the Baronesses handmaidens walked in on the scene, forcing Cicero to kill her as well. From what we know about Cicero’s past up until this point and his decision to include the contract in his personal journal, we can guess that this was the first time Cicero killed anyone outside of his contract target. 

The Adoring Fan Ruse

As mentioned previously, Cicero always gave Adoring Fan vibes from the second I met him. This was due to his slight stature and incredibly annoying voice, teamed with a rather unbecoming personality. Well, it would seem that this aspect of Cicero’s personality may be the result of getting too invested in one of his contracts, something Cicero is known to do. 

According to his journal, on the 27th of Rain’s Hand, 4E 187, Cicero took another contract that would have him pose as the Adoring Fan in order to gain access to the Grand Champion of the Cyrodill. Through some undisclosed means, Cicero manages to travel with the Grand Champion, becoming his companion for a short time. They would soon leave the capitol, journeying through the Great Forest.

This gave Cicero the perfect opportunity to complete his contract, literally stabbing him in the back, taking the much higher-skilled fighter from behind. 

adoring fan
Bethesda is bringing back the ‘Adoring Fan’ in Starfield

The Failing Brotherhood

A major subplot that revolved around Cicero during his time in the Cheydinhal sanctuary was the contraction of the Dark Brotherhood. It would seem that the sacking of the Bruma sanctuary was nothing less than the start of a change in fortune for the Brotherhood. 

As Cicero continued to take contracts, murdering them all and achieving everything he could, continuous meetings between members of the Black Hand and other high-ranking members of the guild continued in the background, with Cicero only hearing the broad strokes.

Many members wished to consolidate what the Brotherhood currently had, going quiet for a short time to protect their sanctuaries and members from further reprisal. Others, however, decided that they should try and expand, stating that diversifying was the only way to prevent extinction. 

Too Little, Too Late

It would seem that a concrete decision was never made within the Black Hand, leaving individual sanctuaries to struggle on their own in a changing world. 

Eventually, it was learned that Bravil and the corpse of the Night Mother were in danger, with bands of drug pushers in the area rising in power. Therefore, the then Listener, Alisanne Dupre, sent several members to the city in order to hopefully regain some form of order. Their task was not to kill but to calm. 

Soon after this, the Listener and the guild’s only contact with the Night Mother, Alisanne Dupree, was killed, with the Night Mother’s corpse falling into danger shortly after. 

Thankfully, though, for every member of the Dark Brotherhood, one of the agents that were dispatched to Bravil, Garnah the Orc, managed to hack his way through citizens and guards alike, escaping Bravil with the Nigh Mother and a lot of near-fatal wounds, including an arrow to the eye. 

He managed to bring the Night Mother to Cheydinhal, collapsing as he arrived. However, this victory was little more than a reprieve.

With the Listener dead and the Night Mother unable to contact her assassins, everyone throughout Tamriel who conducted the Black Sacrament was left without help, leaving the Brotherhood to contract, losing members as contracts dried up. After all, without contracts, the guild could not pay or feed its members. 

spiral skein
The Lucky Old Lady of Bravil

Cicero, The Keeper

As the guild continued to contract and members left the Cheydinhal sanctuary, the safety of the Night Mother became paramount.

Therefore, Rasha, as the last surviving member of the Black Hand, decided to revive an old guild tradition, appointing the most loyal member of her collapsing guild, Cicero, to the role of keeping and guarding the Night Mother. 

This new position was a great honor for Cicero; however, it meant that he was no longer allowed to accept contracts, therefore spelling an end to his murdering days. However, before this role was made permanent, Rasha gave Cicero one last contract to say thank you – the assassination of a court jester. 

This mission was the start of Cicero’s descent into madness. As it was his last ever contract, Cicero didn’t want to leave anything to chance. Therefore, he studied the jester intimately, becoming at one with the man before ever attempting to make a move on him.

When Cicero finally made his move on the jester, he notes in his journal how the target laughed all the way through his death, even on the precipice of Sithis’ void. That laugh would prove to torment Cicero. 

Alone, So Alone

Once Cicero returned to the Cheydinhal sanctuary to take on his role as Keeper, he was met with silence. During his protracted contract, the members of the sanctuary had fully deserted the place and him, leaving him with nobody but the Night Mother’s silent corpse. 

In his fourth journal, Cicero spoke about this time, stating: 

“Silence! Deafening Silence! In my head, in my head, in my head. It is the silence of death, the silence of the Void. Seeping into me, through the Mother. The silence is hatred. The silence is rage. The silence is love.”

While he cared for the corpse of his dear mother, Cicero became obsessed with his final contract, and as his mind started to crumble in that silence, he merged with that laughing victim. During this time, Cicero also became obsessed with becoming the next Listener, conflating his position as Keeper with that of Listener. Of course, the Night Mother never did break her silence. 

dark brotherhood in oblivion
Oblivion – Dark Brotherhood Sanctuary Ambiance (skeleton, white noise, torches)

The Beginning of the End

Eventually, as the Cherydinhal sanctuary dwindled in numbers, Rasha decided enough was enough, claiming that they were the next Listener, having been spoken to by the Night Mother. Of course, in Cicero’s position as Keeper, he was the only one privy to the binding words used to prove whether one is the real Listener or not.

Rasha could not repeat these words, leading Cicero to accuse them of treason and sentence them to death. After Raha’s death, Cheydinhal’s sanctuary was doomed, empty of everyone but Cicero and the Night Mother.  

Cicero remained in this emptiness and silence for eight long years, not hearing another voice for that entire time. He continued to lose his mind and turn himself into the jester we meet in Skyrim. During this time, he would survive on the insects and rodents that would journey into the sanctuary to feed on the Night Mother’s corpse.

Eventually, he was moved to seek another refuge and re-enter the world. After arriving at the docks with the Night Mother’s casket in tow, he boarded a ship for Dawnstar, knowing that Skyrim was the last surviving arm of the Brotherhood. 

Arrival in Skyrim

When Cicero first touched down in Skyrim, he wandered through Dawnstar until he found the Black Door there. After giving the passcode, he entered and found it deserted. Sitting down in this empty sanctuary, he began writing letters to Astrid, the leader of the last surviving branch of the Dark Brotherhood in Skyrim, asking for her help.

Of course, we learn later that Astrid was not too pleased to hear of Cicero and the Night Mother’s arrival in Skyrim, but she could not refuse the request of a Keeper, formally inviting him to take sanctuary in Falkreath. 

During his journey to Falkreath from Dawnstar, the player can bump into Cicero in a chance encounter. This will begin the quest Delayed Burial, wherein the player must help the jester repair the wagon that is carrying his ‘mothers’ casket. Of course, at this time, the player has no idea about Cicero’s true identity or the cargo he carries. 

After this, the player will meet Cicero once again in the Falkreath sanctuary as he arrives just after the player becomes a member. 

cicero transporting the night mother
I was doing the Companions questline and I found Cicero transporting the Night Mother to the sanctuary on a road and I didn’t even join the Dark Brotherhood like how detailed is

Enter the Dragonborn

After the player joins the Dark Brotherhood and completes the Mourning Never Comes quest, they will arrive back in the Falkreath sanctuary to find Cicero and the Night Mother there. It is clear that Astrid is not too pleased with his arrival or the Night Mother’s superseding of her authority, and regardless, he is welcomed with open arms. 

However, during the quest Whispers in the Dark, Astrid confides in the player that she thinks Cicero may be a traitor. Apparently, when no other guild member is in the Night Mother’s personnel resting room, he locks the door.

He begins speaking to someone, conversing, and even answering questions, even though the other voice can never be heard. Therefore, Astrid tasks the player with finding out who Cicero is speaking to and how.

To cut a long story short, the player must enter the Night Mother’s coffin to hear Cicero’s traitorous words. However, it isn’t long until you learn that he is simply insane and conversing with a mute corpse. Of course, the Dragonborn will also be revealed to be the Listener at this time, leaving Cicero irate and Astrid quietly seething. 

After this, there is a period where Cicero is quite confrontational with the player before acquiescing to your new position and favor with the Night Mother, eventually becoming respectful towards the player.

Attacking the Falkreath Sanctuary

After Astrid sends the Dragonborn on meaningless contracts for the Brotherhood, probably in an attempt to wrestle power away from the player and the Night Mother, Cicero confronts Astrid in the sanctuary. 

As the player does not witness this, we hear about it from Veezara, who tells the player that after Astrid challenged the authority of the Night Mother, Cicero flew into a rage over the disrespect and Astrid’s disregard for the first of the five tenets. This rage overtook the small jester, forcing him into a tight spiral of knives and fury.

He would wound several in the sanctuary before fleeing to the Dawnstar home of the Brotherhood with Arnbjorn hot on his tail. Astrid subsequently sends the player after the two to help kill Cicero. 

falkreath sanctuary interior
The Falkreath Sanctuary interior from TES Skyrim

A Possible Cure for Madness

After you reach the Dawnstar sanctuary, you will find Arnbjorn bleeding heavily outside of the Black Door. Apparently, Cicero managed to get a good couple of hits in before fleeing inside. 

With Arnbjorn unable to pursue, the player must enter and find the jester, deciding whether to kill or spare him. Should the player decide to kill Cicero, his story will end there and then at your hands. However, if he is left alive, he will remain in the Dawnstar sanctuary. 

When the quest Hail Sithis! is completed and Cicero has been left alive, he will automatically update, becoming an essential and unkillable NPC. After this, the player will also be allowed to recruit Cicero as a follower. Having the jester as your follower is not for the faint-hearted, as he will keep going with that voice of his for the rest of the game while routinely breaking out into dances as you travel around Skyrim with him.

killing cicero
Do you guys kill Cicero or let him live?

Unique Items

As anyone who has ever played Skyrim before already knows, Cicero dresses slightly differently from the rest of the NPCs in Skyrim, coming equipped as a court Jester throughout the game. 

His Jester’s outfit, which the player will undoubtedly want to get their hands on, is unique in the game, with only two sets available throughout. There is one on Cicero’s body when you kill him, this outfit cannot be pickpocketed off of him, and there is another on the table in the Dawnstar sanctuary.

However, this version of the jester outfit is much weaker than the one Cicero wears. Let’s look at this outfit and the bonuses it can give you should you choose to kill Cicero. 

Jester’s Clothes

  • Enchantment: Prices and one-handed attacks are 12% better.
  • Armor: 0
  • Weight: 1
  • Value: 1163

Jester’s Boots

  • Enchantment: Wearer is muffled and moves silently.
  • Armor: 0
  • Weight: 1
  • Value: 305

Jester’s Gloves

  • Enchantment: Double sneak attack damage when performed with a one-handed weapon.
  • Armor: 0
  • Weight: 0.5
  • Value: 125

Jester’s Hat

  • Enchantment: Increases sneak by 30%.
  • Armor: 0
  • Weight: 0.5
  • Value: 1806

Cicero Skyrim Guide: FAQs

Question: Should I Kill or Spare Cicero in Skyrim?

Answer: In my opinion, you should spare Cicero. While he may be crazy, Astrid proves later in the Brotherhood’s quest to disobey the Night Mother and her five tenets by betraying the Dragonborn. Therefore, Cicero was well within his rights as Keeper to attack Astrid when she challenged the Night Mothers’ authority.
In the end, he may be a little bit crazy, but he is also a loyal and honest guild member that is different enough to warrant his life. At the very least, he is a little reprieve from the all-to-serious world that Skyrim can be at times. 

Question: What Happens if You don’t Kill Cicero? 

Answer: Whether you kill Cicero or not, nothing will change in the main Dark Brotherhood quest; Cicero will merely hide in Dawnstar until the ‘Hail Sithis!’ quest is complete, becoming a possible follower after this point.

Question: Can I Turn Cicero into a Vampire?

Answer: Cicero cannot be married and has a unique voice in the game, so the player cannot turn him into a vampire. Many uniquely voiced characters in the game cannot, as the original voice actors did not record the necessary lines. 
So, there you have it, a complete and comprehensive guide to one of the most interesting characters in all of Skyrim and TES at large.
The sheer amount of content and backstory we get regarding Cicero via his journals is amazing, allowing us to completely follow his descent into madness and determine whether or not he truly deserves to be killed or spared. 
I really hope you enjoyed this Skyrim guide and found the information both interesting and informative. Regardless, I look forward to seeing you again soon; happy playing!

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