Cicero is an eccentric jester, and the Keeper of the Night Mother's coffin. He is found on the road north of Whiterun, near Loreius Farm, transporting the coffin of his "mother." After this encounter, he may be found within the Falkreath Sanctuary and later the Dawnstar Sanctuary, depending on the Dragonborn's progress through the Dark Brotherhood questline.

Cicero has five journals that are scattered throughout his room at the Falkreath Sanctuary, telling the story of his slow descent into madness.

As is detailed by his journals, Cicero was once a member of the Bruma Sanctuary before it was destroyed and later a member of the Cheydinhal Sanctuary, and was renowned for his cloak-and-dagger killing style. He mentions riots in Bravil leading to the death of Alisanne Dupre, the Night Mother's previous Listener, and the desecration of the Night Mother's crypt beneath The Lucky Old Lady. Voted Keeper of the Night Mother by the remaining Brotherhood members, Cicero fulfilled one last contract before starting his new duties; he was scheduled to kill a jester, with whom he slowly became obsessed. His attire and flamboyant manner mimic this jester.

He ordered Garnag, a fellow Brotherhood assassin, to murder Rasha, a member of the Black Hand who had falsely claimed to be the next Listener. Eventually, through the months after the last Listener's death, the remaining Brotherhood members left the Sanctuary to look for contracts or food and never returned, leaving Cicero trapped alone in the Cheydinal Sanctuary. Eventually, he grew more and more insane from obsessing over his last kill, isolation, and due to trying to talk to the Night Mother and become her Listener. Eight years later, he wrote letters to Astrid in Skyrim to appeal for sanctuary, fleeing from Cheydinhal to Skyrim with the Night Mother's coffin.