Cicero is an Imperial assassin and “The Keeper” of the Dark Brotherhood, whose responsibilities consist of caring for the Night Mother’s body and casket. Prior to the player joining the Dark Brotherhood, he can be found on the road to Whiterun, just northeast of Whitewatch Tower near Loreius Farm.
Like many of the Dark Brotherhood assassins, Cicero takes on a persona to get closer to his targets. He refers to himself as a jester and wears a full set of unique Jester’s clothing accordingly (The outfit provides slightly stronger enchantments compared to the standard set). In combat he wields a leveled dagger. He is considered eccentric by many other characters and can often be seen dancing amusingly.
When you first meet him near Whitewatch Tower, his wagon carrying his “mother” has broken down. Talking to him will start the quest Delayed Burial. Cicero takes an active role in the Dark Brotherhood questline, and his arrival at the sanctuary with the Night Mother’s body causes much commotion. Some members of the guild are happy to have the Night Mother and her Keeper present, while others view them as a threat to the new way of running the organization. Cicero’s ultimate goal in being the Keeper is to locate the anointed Listener, as there has not been one for years. When the Night Mother speaks to you, Cicero announces that you are the new Listener of the Dark Brotherhood, which only fuels the debate over who is actually in charge of the guild.
While the player is away on a contract, Cicero overhears Astrid saying disrespectful things about the Night Mother and attacks the guild members, but flees after failing to kill Astrid. Upon returning to the sanctuary, you are tasked with tracking down and killing Cicero. After reading his journal, it turns out he has fled to the abandoned Dawnstar Sanctuary. While fighting your way through Spectral Assassins, Cicero will repeatedly mock the player. When you finally reach him, he is already wounded, giving you the choice to kill him or leave him. If you opt to attack him, he will suddenly stand up and attack you. Despite being ‘wounded’ he will have full health. Regardless of what you choose, you must then deliver the news to Astrid (by lying if you chose not to kill him). If you spare Cicero, he will return to the Brotherhood after the questline has been completed, and can serve you as a follower. If you give Cicero one of the execution hoods from one of the first Dark Brotherhood quests, he will wear it.
Long before the events of Skyrim, Cicero was a professional assassin who was welcomed into the Cheydinhal Sanctuary and became known for disguising himself while hunting his targets. At some point Cicero started writing a journal about the riots in the streets of Bravil, which ultimately led to the death of the previous Listener as well as the destruction of the Night Mother’s crypt. Cicero frequently comments on how the Dark Brotherhood is losing its refuges and influence; eventually, he was voted the Keeper of the Night Mother, a position he was both honored and saddened to fill, as he was no longer able to take contracts. However, before being made Keeper, he was given one last contract to carry out. His job was to kill a jester and, being his last contract, Cicero became obsessed with his target. Later on he began to think about the jester and how he was smiling in death. This had implications later when he began to lose his mind: Cicero remembered how his last target seemed happy in death and inevitably took on both the apearance and demeanour of the jester. Cicero gradually went insane over his inability to talk to the Night Mother, and being trapped alone in the Cheydinhal Sanctuary, ended up killing a fellow assassin who tried to proclaim himself Listener.