Widely regarded as bothersome, obnoxious, strange, and insane, Cicero sports flamboyant attire and often speaks with a high-pitched voice. Cicero speaks to both himself and the Night Mother's remains often, and as such, he is considered psychotic. As Keeper of the Night Mother, Cicero takes his vocation very seriously, willing to wound or even kill anyone who questions or ignores the Night Mother's authority, although he was not always like this; as evident from his first two journals, before becoming Keeper, Cicero was quite sane, comparatively speaking. His final contract involved killing a jester, and slowly, while most of his fellow assassins were being killed in Cyrodiil, Cicero descended into madness, obsessing over the jester, and adopting aspects of the jester's persona. He wears a red and green jester costume and ebony daggers.

Astrid is the leader of the Dark Brotherhood in Skyrim and wife of another Dark Brotherhood member, Arnbjorn. She resides in the Dark Brotherhood Sanctuary, near Falkreath, and holds the responsibility of finding new recruits in the Night Mother's absence. Astrid decrees her authoritarian leadership to be "stronger" than The Five Tenets. She tires of the laws and restrictions that limit the Brotherhood, deciding that a sort of family-like unity benefits the members of the Brotherhood better than rigid structure.