Cicero Skyrim Guide: The Jester Assassin Agent of the Night Mother

When you think of The Elder Scrolls V: Skyrim, you think of wide open spaces, rocky mountains, and gigantic dragons terrorizing the citizens of Skyrim.

However, when I think of Skyrim, I think of all the cool, funny, and great characters that I meet on my adventure. Cicero may be one of Skyrim’s most iconic followers and characters and sits between Brynjolf and Serana as one of my favorite characters in Skyrim.

Cicero is an odd character that I feel is a deeply misunderstood character in the game. His story in Skyrim and the Falkreath Dark Brotherhood Sanctuary is as tragic as his past. Many NPCs hate Cicero and feel uncomfortable in his presence, but there are two things that no one can deny.

  1. Cicero is a deadly assassin.
  2. His devotion to the Sithis and the Dark Brotherhood is unmatched.

Cicero is a complex character; there’s so much mystery behind his manic laughter and jittery dancing. So without further ado, let’s heed the Night Mother’s call and shout Hail Sithis!

Key Cicero Details Up-Front

Don’t worry if you’re short on time and have assassinations to make and contracts to complete, don’t worry. I’ve got all the important details of your favorite dancing clown right here:

It would be best if you capitalized on Cicero’s rogue skills by giving him better daggers and a bow. It’s best to equip Cicero with the Shrouded Armor, as his current outfit has no Armor Rating

  • One-handed: 100
  • Sneak: 100
  • Archery: 97
  • Light Armor: 97

To acquire Cicero as a follower, you must spare his life during “The Cure For Madness” Dark Brotherhood quest and complete “Hail Sithis!” the final quest in the Dark Brotherhood storyline. 

Here is a list of all the quests you can expect to encounter Cicero:

  • Delayed Burial
  • Whispers in the Dark
  • The Cure For Madness

However, as a member of the Dark Brotherhood, the player can talk to Cicero and read his journals found in his room in the Falkreath Sanctuary. After Cicero is made a follower, he will return to the Dawnstar Sanctuary if the player is to disband him.

Cicero: Assassin Turned Jester

cicero assassin turned jester

Cicero wasn’t always the quirky dark jester we know and love today. He has been a loyal servant of Sithis and a member of the Dark Brotherhood for many years. Once Cicero has joined the Dark Brotherhood, the Dragonborn can find journals in Cicero’s quarters dating back fifteen years.

Cicero’s second journal entry of volume one explains that he relocated to the Cheydinhall Sanctuary and was met with open arms by the other sanctuary members.

At this point in history, Dark Brotherhood Sanctuaries across Cyrodil are systematically being wiped out. Cicero remarks on this in his journal, mentioning the destruction of the Sanctuary in Bruma.

Interestingly Cicero mentions in an early entry in his journal.”There are rumors that the Black Hand is split on our continued direction. Some favor expansion, the others consolidation.

My personal feeling is that the Dark Brotherhood needs to, at the very least, maintain the illusion of being everywhere at once.” This is some great foreshadowing of the split of ideals in Falkreath Sanctuary in Skyrim.

If the Dragonborn makes the prerequisites to obtain Cicero as a follower, it would be the second time Cicero has followed a Listener in the Dark Brotherhood. In his journals, Cicero states that he respected Alisanne Dupre and followed her through her journey as Listener.

Alisanne Dupre died defending the Crypt of the Night Mother from her stepfather Uther Nere, and his mages. The player can play through this event in The Elder Scrolls: Legends: The Fall of the Dark Brotherhood.

Cicero highlights his respect for Alisanne Dupre in his journal, stating, “If the crypt is discovered, Alisanne Dupre will, of course, protect the remains of the Unholy Matron until her dying breath,” and thats exactly what she does.

Cicero would only take on the persona of a jester once the Sanctuary leader revealed that Cicero had been selected to become the Night Mother’s Keeper. Cicero was honored to be deemed worthy of the role.

However, this would mean he could no longer fulfill Dark Brotherhood contracts. He was given one final contract before taking up his new duties as Keeper, one that would change Cicero forever.

Cicero Descends into Madness or is Enlightened. You Decide

Cicero fulfilled his last contract with a slip of his knife; a court jester lay on the floor manically laughing to his last dying breath. Months after completing the contract, Cicero mentions that it has been a long time since he got to use his blade and how he misses it. He goes on to state:

“I think back fondly on my hours with the jester. His laughter, his screams, his pitiful cries. And then, as the end drew near, his laughter once more. Merry in death as well in life. I was honored to know him”.

This is one of the most telling journal entries that give a good insight into Cicero’s loyal but dark and terrifying mind. The entry exposes that Cicero misses killing and how he has become fixated on the dying jester through a combination of addiction to murder and the jester’s devotion to his craft, manically laughing until the end.

Cicero fell deeper into the jester persona after losing more members of the Cheydinhall Sanctuary after it was raided. However, it’s Volume Four of his journal where Cicero fully embodies the jester, writing that he believes the jester he can hear laughing in his head is a gift from Sithis himself.

Although speculation, I believe this could mean one of two things: (The latter is my favorite theory)

  1. Cicero suffers from adverse mental health issues brought on by the events that have unfolded in the Cheyinhall Sanctuary or from killing people.
  2. Cicero has been chosen as the Night Mother’s Keeper, and Sithis has reached out to Cicero using the jester’s soul to communicate with Cicero as a reward for his devotion and persistence to talk to the Night Mother.

Cicero’s Strengths and Weaknesses

cicero's strengths and weaknesses

Cicero has very high stats making him a fantastic follower to explore Skyrim. Here is a breakdown of his strongest stats:

  • One-Handed Skill: 100
  • Sneak: 100
  • Light Armor: 97
  • Archery: 97
  • Alteration: 61

As you can see, Cicero is one of the best rogue characters in the game. He is not only skilled in One-handed weapons, preferably daggers. But also has mastered the Archery skill.

Therefore, it’s a good idea to trade Cicero a bow; however, bear in mind that you will have to supply Cicero with arrows. Moreover, it’s best to capitalize on his high Light Armor skill level by trading him Shrouded Armor, as his current outfit has no Armor Rating.

A large portion of Cicero’s quests revolves around the Dark Brotherhood, considering Cicero is a veteran member of the guild. However, this doesn’t make Cicero trusted anymore by the Dark Brotherhood members of the Falkreath Sanctuary.

That said, Cicero is a loyal subject of the Night Mother and Sithis, and many of his actions are made because of his loyalty to these deities.

Here are all the quests that revolve around our favorite court jester:

  • Delayed Burial
  • Whispers in the Dark
  • The Cure For Madness

Delayed Burial

The “Delayed Burial” quest is one of the first quests the player can obtain in the game and is the first quest where you’ll meet Cicero. You can start the “Delayed Burial” quest by traveling north from the Whitewatch Tower north of Whiterun to Loreius Farm.

Cicero can be found on the road at the foot of the path to Loreius Farm; he will explain to the player that he is relocating from Cyrodil to Skyrim, but his carriage broke down, and now he needs a new wheel to continue his trip.

There are two options to the “Delayed Burial” quest; you can either:

  • Convince Vantus Loreius to fix Cicero’s carriage.
  • Report Cicero to a Whiterun Guard for Vantus Loreius.

If you convince Vantus to fix Cicero’s carriage, Cicero will later thank the Dragonborn for helping reach the Falkreath Sanctuary along with the Night Mother’s corpse.

If you report Cicero to a guard, he will later explain that he is unhappy with your decision and will kill Vantus Loreius and his wife.

The Dragonborn can return to the Loreius Farm after the quest is complete to find a guard warning the Dragonborn to stay out of the farmhouse as the owners have been slaughtered, adding his fear at the sight of the corpses stating, “So many stab wounds.” (I wonder who that was).

Convincing Vantus Loreius to fix Cicero’s carriage wheel is the best option. Considering that Cicero will arrive at the Falkreath Sanctuary regardless of the Dragonborn’s decision.

Whispers in the Dark

cicero - whispers in the dark

At the time of the “Whispers in the Dark” Dark Brotherhood quest Astrid and many other Dark Brotherhood companions have shared that they are uncomfortable with how Cicero behaves and don’t trust his intentions, and although Cicero has deep loyalty to the Dark Brotherhood and the Night Mother he is an absolute mad lad so I can see where the members are coming from.

The “Whispers in the Dark” quest is a creepy quest where the Dragonborn must hide in the Night Mother’s coffin in the Night Mother’s Chambers to eavesdrop on Cicero’s odd babblings.

While inside the coffin, the Night Mother will talk to the Dragonborn, asking them to take contracts from Amaund Motierre residing in the Dwarven Ruins of Volunruud and say, “darkness rises when silence dies” to Cicero.

The coffin opens once the conversation is over, and Cicero goes ape after seeing the Dragonborn just stepping out of a coffin. Astrid walks into the chambers, and Cicero jumps for joy, learning that the Dragonborn is the Night Mother Listener after the Dragonborn says, “Darkness rises when silence dies.”

Feeling as though her position is threatened, Astrid orders the Dragonborn to ignore the Night Mother’s requests until she has “assessed” the situation. Creating a small divide in the Falkreath Sanctuary that will only grow bigger with time.

  • At the quest’s end, the player will become the Listener of the Night Mother and gain Cicero’s trust.

The Cure for Madness

After killing dozens of citizens of Skyrim and making a small fortune from killing NPCs, the player will be given the most controversial contract yet: Cicero!

This is for a good reason, or so it seems. Astrid explains that Cicero tried to kill her and wounded Veezara. Nazir explains that while Cicero was attacking Astrid, he was “Ranting and raving. About the Night Mother, how she was the true leader of the Dark Brotherhood, and Astrid was just a “pretender.” 

We learn from Astrid that her husband Arnbjorn chased after Cicero when he fled the Falkreath Sanctuary and that she wants you to make sure he’s okay. She orders you to search Cicero’s room for clues on where he might have disappeared to. (this is where you pick up the Final Volume of his journal).

The Dragonborn learns from Cicero’s journal that he has fled to the Dawnstar Sanctuary and the Night Mother to live by the old ways of the Dark Brotherhood and answer to the Black Sacrament. 

  • The player obtains Shadowmere from the dark pool outside of the Falkreath Sanctuary during “The Cure For Madness” quest.

Accompanied by your new shadowy four-legged friend, travel to the Dawnstar Sanctuary on the beach north of the seaside town. You will find Arnbjorn wounded outside the Sanctuary. 

  • To enter the Sanctuary, the Dragonborn must speak the passphrase “Innocence, my Brother” once the Black Door has asked, “What is life’s greatest illusion.”

The player can find the Jester Outfit on the left table in the first room. After picking this up, the player must navigate through the sanctuary dodging traps and killing Sanctuary Guardians. 

Finally reaching Cicero, the player will be given two decisions:

  • Kill Cicero
  • Leave the Sanctuary

I recommend leaving the Sanctuary, as killing Cicero doesn’t impact the story of the Dark Brotherhood, and it’s a waste of a follower!

The story continues with Astrid backstabbing the Dragonborn in return for the Dark Brotherhood being left alone by the Imperial Empire. However, it doesn’t go to plan, and Astrid’s actions end up killing most of the Falkreath Sanctuary members in the “Death Incarnate” quest. Astrid is burned to death, just as Alisanne Dupre in the Cheydinhall Sanctuary. 

Cicero as a Follower

cicero as a follower

Cicero can be acquired as a follower if the Dragonborn decides to spare Cicero’s life at the end of “The Cure For Madness” Dark Brotherhood quest and the “Hail Sithis!” the final Dark Brotherhood quest has been completed.

The surviving members of the Dark Brotherhood do not react to Cicero, and he has no impact on the remaining Dark Brotherhood quests. Therefore there is no reason to kill Cicero in “The Cure For Madness” quest.

  • If you disband Cicero as a follower, he will return to the Dawnstar Sanctuary instead of the Falkreath Sanctuary. 

Cicero makes a fantastic and reliable follower. His high sneak stats make him formidable in battle, and his level hundred One-handed makes him deadly with a blade. He can often be found dancing when idle. However, I recommend you trade with Cicero to equip him with better gear.

Cicero’s Unique Equipment

Cicero’s Outfit is a unique set of enchanted clothing that can only be obtained by pickpocketing or looting Cicero’s body after choosing to kill him in “The Cure For Madness” Dark Brotherhood quest.

Cicero’s Outfit isn’t the greatest outfit for an assassin, as the outfit will grant you a whopping zero armor in total! On the other hand, it has some amazing enchantments for sneaking around and stealing Whiterun Guard’s Sweet Rolls. However, these enchantments are not too dissimilar to the Dark Brotherhood Shrouded armor set. Let’s take a closer look:

  • Cicero’s Hat: Increase the Sneak skill by 35%.
  • Cicero’s Clothes: 20% better prices bartering. One-handed attacks are 20% better.
  • Cicero’s Gloves: Double damage from One-handed sneak attacks.
  • Cicero’s Boots: Allows the wearer to move silently.

The enchantments are fantastic; however, the lack of armor is a death sentence if you get caught while sneaking. The basic Shrouded Armor is much better as a full set grants the wearer a fifty-eight armor rating along with the following enchantments:

  • Shrouded Cowl: Bows deal 20% more damage.
  • Shrouded Armor: Increases Poison Resistance by 50%.
  • Shrouded: Gloves: Double damage from One-handed sneak attacks.
  • Shrouded Boots: The user moves silently from muffled movement.

It could be argued that Cicero’s Outfit is much lighter, weighing less than three units compared to the thirteen units of the Shrouded Armor set. However, this is negligible weight from both armor sets. Even Cicero seems to notice how bad his armor is and will equip any armor you trade him.

The Shrouded Armor set can easily be obtained by killing Dark Brotherhood Assassins or joining the Dark Brotherhood guild.

Suppose you want to match Cicero’s clownish style and travel together as a weird creepy clown duo. In that case, you can obtain his Jester Outfit in the Dawnstar Sanctuary entrance during “The Cure For Madness” Dark Brotherhood quest.

  • The Jester Outfit is almost identical to Cicero’s outfit featuring the same but weaker enchantments of Cicero’s Outfit.

Cicero is a skilled assassin, evident from his taking on several Dark Brotherhood members and Astrid before “The Cure For Madness” Dark Brotherhood quest. Cicero will cut through Trolls like a dragon’s wings in the air. I recommend giving Cicero two daggers to capitalize on his maxed Sneak and One-handed skill. Here are the best daggers in The Elder Scrolls V: Skyrim 

Cicero’s Hauntingly Funny Quotes

cicero's hauntingly funny quotes

Because Cicero takes the persona of a jester, he speaks in rhyme and is constantly joking and laughing. I’m not going to lie; Cicero has scared me many times with his creepy voice and dialogue.

I remember my buddy and I leaving Skyrim on my Xbox 360 and coming back after food, forgetting it was on, and hearing him enthusiastically say, “Let’s kill someone.” through my TV. My buddy and I thought this was hilarious at the time, and to this day, it’s one of my favorite Cicero voice lines.

It’s equally terrifying alt-tabbing out of the game, forgetting it’s on, and hearing him sing a song about stabbing people while I write this article!

If you don’t know by now, Cicero has some iconic quotes. Some players may find him annoying, and while he’s one of my favorites, you can get Cicero’d out. There are so many great lines of dialogue, so I’ve only included my favorites and lines from major events; enjoy:

  • “madness is merry, and merriment’s might, when the jester comes calling with his knife in the night.”

This is a scary one as you can see Cicero’s embodiment of the jester in full force makes him sound like a monster.

  • “Cicero is hungry… …need a sweetroll… or a carrot”
  • “the High King’s court needs a jester… But not me. No, not Cicero. The Fool of Hearts is busy enough, thank you very much”

Cicero is a jester, so he does have some comedy relief every now and again, and these two are some of my favorite lines. The delivery is perfectly timed.

  • “Hmm… That’s like telling you about the cold of space, or terror of midnight. Sithis is all those things. He is… the Void.”
  • The Night Mother’s crypt in Bravil was… desecrated. The Imperial Province is ravaged by strife. Nowhere there is safe, at present. So Cicero brought our Lady to her new home. Here! This is the only Sanctuary left in all of Skyrim, you see. Such was my… honor. As Keeper.”

The Dragonborn can talk to Cicero to gain insight into his backstory before Cicero arrives in Skyrim and information regarding the Night Mother and Sithis. Let me tell you, the dialogue and voice acting is chilling when the Dragonborn asks, “Tell me about Sithis.”

Many of the characters in Skyrim are voiced by the same actors as a way for Bethesda to cut costs. However, Cicero is voiced by a completely separate voice actor, making him a unique follower to have around. However, I must admit Cicero’s voice makes my ears cringe on occasion (he makes some weird sounds!)

Cicero’s Character Relationships

cicero's character relationships


Cicero dislikes Astrid because she breaks the Five Tenets of the Dark Brotherhood, distrusts Cicero, and hates that leadership over the Falkreath Sanctuary is contested by the Listener and Keeper.

The Five Tenets is a book found in The Elder Scrolls IV: Oblivion that contains five rules that all Dark Brotherhood members should follow. Breaking the Five Tenets will supposedly anger Sithis.

Night Mother

Cicero has been the Keeper of the Night Mother for years, and he cares deeply for her, tending to her coffin and corpse. (gross) Cicero wants nothing more than to become the next Listener so that he can restore the Dark Brotherhood to its former glory, but no matter how many times he talks to the Night Mother, she never replies.

During the “Whispers in the Dark” Dark Brotherhood quest, the Night Mother talks to the Dragonborn, whispering, “Poor Cicero. Dear Cicero. Such a humble servant.

But he will never hear my voice. For he is not the Listener.” This shows that although Cicero cannot speak to the Night Mother, his voice has not gone unheard, showing that the Night Mother cares for Cicero.


Cicero tricks the Dragonborn when returning to the Dawnstar Sanctuary, stating:

“Oh yes, it is Cicero! You were a fool to spare me. What, did you think I would be grateful? Cicero should be Listener! Not you! Now you will die! … Ahhh…. gotcha! Oh, Listener, you should see the look on your face! Ha ha ha ha ha ha ha! Oh, Cicero has returned! Not to kill the kind Listener, but to serve, until one of us dies horribly, in service to our Mother! Best friends forever!

Cicero used to follow Alisanne Dupre, the previous Dark Brotherhood Listener in Cyrodil, before she was killed defending the Night Mother in Cyrodil.

Many of the previous events in the Dark Brotherhood in Cyrodil foreshadow the events in Skyrim. The relationship between the Keeper and Listener is naturally strong because of each chosen member’s role.

Sithis Awaits in the Void

cicero skyrim

In conclusion, Cicero is a fantastic assassin follower to join on your adventures across Skyrim. His quirky personality is funny and, if not a bit scary, brings a lot of smiles and laughs listening to his remarks on specific quests and locations the Dragonborn is in.

Many fantastic characters can be obtained as followers in The Elder Scrolls: V Skyrim, from the fearless maiden warrior of Riften Mjoll the Lioness or the friendly and reserved vampire Serana.

Cicero is one of these followers that stands out from the rabble of Skyrim. He is a skilled rogue equipped with the right daggers and can deal severe damage thanks to high stats.

Even if you find Cicero creepy and don’t like him as a follower, Cicero is a significant character in the Dark Brotherhood storyline and Skyrim in general. His story paints a great picture of Cyrodil during the Great War between the White Gold Concordant and the Empire, the events that lead up to the beginning of Skyrim.

Cicero is a troubled soul who has found sanctuary and family within the Dark Brotherhood. While it’s impossible to know his past before he joined the Dark Brotherhood fifteen years ago, his entries show a character who has been a devoted servant of Sithis and the Night Mother, always protecting the “old ways” of the brotherhood and staying loyal to those in the order.


Question: How Can I Join the Dark Brotherhood in The Elder Scrolls V: Skyrim?

Answer: To join the Dark Brotherhood, you must travel to Winderhelm to start the “Innocence Lost” quest. The quest is acquired by talking to Aventus Aretino, a child who performs the Black Sacrament ritual to summon the Dark Brotherhood.
You can find Aventus Aretino in the Aventus Residence in Windhelm. You can start the quest at any character level and as soon as you get to Whiterun by using the Transport Carriage.
The “Innocence Lost” quest will task you with killing Grelod the Kind in the Honorhall Orphanage in Riften. You can kill Grehold before accepting the “Innocence Lost” quest to complete the quest on talking to Aventus Aretino.
After completing the quest, you will receive a letter from the Dark Brotherhood marked by the symbolic black hand and a short message reading “We Know.” To progress to the next Dark Brotherhood quest, “With Friends Like These…” by sleeping in a bed.

Question: Is it Worth Playing The Elder Scrolls: Legends Trading Card Game?

Answer: It’s worth playing The Elder Scrolls: Legends, even if you’re not a fan of TCGs, as the game follows a great story of the player dubbed the Forgotten Hero and a band of allies fighting Lord Naarifin, a High Elf general during the Culling as the Aldermi Dominion releases Daedric creatures into Tamriel in a bid to destroy the Empire.
The Elder Scrolls: Legends has several expansions; however, only three revolve around key events in Elder Scrolls history, such as:
The Fall of the Dark Brotherhood
Isle of Madness
Return to Clockwork City
Bethesda is no longer creating new content for the game. You can play The Elder Scrolls: Legends for free on IOS, Android, Nintendo Switch, PlayStation 4, Xbox One, Microsoft Windows, and macOS.

Question: Can You Visit the Cheydinhall Dark Brotherhood Sanctuary in The Elder Scrolls IV: Oblivion?

Answer: Yes, the main Dark Brotherhood Sanctuary in Cyrodil is based in Cheydinhall. It’s where you obtain Dark Brotherhood contracts from Ocheeva and Vicente Valtieri. You can find the Cheydinhall Sanctuary under the Abandoned House east of the Great Chapel of Arkay.
To join the Dark Brotherhood in The Elder Scrolls IV: Oblivion, the Hero of Kvatch must kill an innocent NPC and sleep in a bed. The player will awake to Lucien Lachance explaining that the murder has pleased the Night Mother and will give you your first Dark Brotherhood contract.

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