Of all the memorable characters in The Elder Scrolls 5: Skyrim, Cicero ranks very near to the top. The colorful jester's flamboyant personality, third-person speech pattern, and unique look make him stand out among the many warriors, creatures, and mages the Dragonborn encounters in Skyrim. Players seem to either love or hate Cicero, but none can deny that he's a fascinating character.
The Dragonborn can meet Cicero early on near Whiterun and choose to help him repair his broken-down cart. It's an innocent enough interaction (even though Cicero is transporting the corpse of the Night Mother), and upon meeting him for the first time players might not know that Cicero is one of the primary figures in the Dark Brotherhood questline. The Dark Brotherhood is one of the creepiest questlines in Skyrim and is arguably the darkest guild the Dragonborn can associate within the entire game, so the presence of a jester doesn't make a lot of sense at first. But, despite his annoying personality, Cicero steals the show in the Dark Brotherhood storyline.
Cicero's Backstory is a Slow Descent Into Madness
Skyrim has a ton of lore that helps shape the world, as anyone familiar with the game will know. However, Skyrim does a great job of making sure that all the primary characters have fully developed backstories as well. Even if they aren't explicitly explained through dialogue, most prominent characters have backstories that can be discovered by reading or by careful exploring. Cicero is one of those characters.
During the Dark Brotherhood questline, players can discover five of Cicero's journals. Reading through them proves one very significant detail: Cicero wasn't always a lunatic. Rather, he was driven to madness by isolation and obsession. Characters that experience a slow descent into madness have always been fascinating, and dominate a big part of the entertainment industry. Walter White from Breaking Bad and DC's Harley Quinn are classic examples of this sort of character arc.
Characters who start out as sane, even likable, and slowly morph into monsters are fascinating because people want to understand what drove them to that point, and there are tons of questions that come to mind. Does insanity come from experiences, or do those experiences just act as catalysts for something that was already there? Can insanity be cured? The list goes on, but Cicero falls into this category of characters.
Cicero Has a Fascinating Reason for Being a Jester
Cicero joined the Dark Brotherhood at a young age and, while always dangerous as an assassin, he was relatively normal and wasn't a jester. It wasn't until he was chosen to be the Keeper of the Night Mother's body that he began to lose his mind. Because the Keeper isn't allowed to act as an assassin for the Dark Brotherhood, Cicero had to complete one final mission before devoting himself fully to the Night Mother. It's no coincidence that his last target was a court jester.
After becoming the Keeper, Cicero was left alone in the Cheydinal Sanctuary for eight years, with no one to talk to other than the Night Mother. She never spoke back, but Cicero began to obsess over her and over his last mission. Hauntingly, he slowly began to assume the jester's persona and became the dangerous clown players know him as.
It's never explained who this jester was or why the Dark Brotherhood had a contract on him, but he left a profound mark on Cicero. It seems unlikely that Cicero would feel guilty at completing this contract, seeing as he'd been an assassin for several years prior. But his unsettling transformation puts him in the same group as characters like Norman Bates.
The jester's death had a massive impact on Cicero and as a result, he adopted his persona and the original Cicero disappeared. It's creepy, and the mystery behind it is part of what makes Cicero such a captivating character. His backstory makes him one of the most interesting characters in Skyrim and definitely the most interesting person in the Dark Brotherhood questline.
The Dragonborn Can Hire Cicero as a Follower, and He's One of the Best
After completing the Dark Brotherhood story, players who decided to spare Cicero's life have the opportunity to hire him as a new follower. And as it turns out, he's one of the best available followers in the game. He's considered essential, which is important because it means he can't die like so many other followers, and he has great statistics as an assassin.
Cicero isn't likely to suit everyone's style, and he can get annoying after a while. For those that can put up with him, though, he can be extremely useful. There aren't a lot of amazing followers in Skyrim, and while it's important to choose one that compliments the Dragonborn's build and makes up for their weaknesses, Cicero is about as good as it gets. Having a good follower can be a game-changer in difficult encounters and it's a great reward for completing the Dark Brotherhood questline. It's also refreshing to have a follower with more of a personality. Cicero keeps things entertaining.
If players chose to kill Cicero at the end of the Dark Brotherhood questline, they can get other followers from the Dark Brotherhood that have equally high stats, but where's the fun in that? Cicero has a far more developed personality and backstory than the other options and he adds something special that no other follower can. He's even been known to dance at random times, a characteristic entirely unique to him.
Apart from the practical reasons behind hiring Cicero as a follower, it's also worth noting that he truly respects the Dragonborn. Not all everyone does, and some followers, like Lydia, are practically forced to tag along and have no real reason to care about the player. But in Cicero's case, the Dragonborn has proven themself to Cicero by becoming the Listener, the only person who can speak with the Night Mother, and by siding with him. Cicero wanted to be the Listener himself and spent many years in isolation trying to communicate with the Night Mother, but he accepts the rejection and congratulates the player nevertheless.
The Dragonborn isn't always Cicero's favorite person in the world, and that's fine, but it can be nice to have a follower that feels honored to tag along. Cicero isn't the only follower out there that respects the Dragonborn, but it's a nice little bonus for those who choose to keep him around. With his interesting backstory and colorful personality, Cicero is a standout character in the Dark Brotherhood storyline and in Skyrim as a whole. Even though he's not every player's cup of tea, it's still well worth paying him a visit for the experience alone.
The Elder Scrolls 5: Skyrim is available on Nintendo Switch, PC, PS4, and Xbox One.