I still remember the first time I joined the Dark Brotherhood. It was about a week after Skyrim’s release, and I’d called in “sick” to work—a tradition I’ve maintained for every Elder Scrolls launch since Morrowind. My apartment was a disaster zone of empty energy drink cans and microwave dinner containers. I hadn’t showered in two days. My cat kept giving me these judgmental looks from atop the bookshelf, like “Really? Another 16-hour gaming session?” Yes, Whiskers, really.
I’d been putting off the Dark Brotherhood questline because I knew what was coming. See, I’d been a massive fan of Oblivion’s Brotherhood—easily the best faction questline in that game—and I was worried Skyrim couldn’t possibly live up to it. Remember that mission in Oblivion where you had to drop the mounted head on the guy during his dinner party? Or the one where you locked a family in their burning house? Dark stuff, but damn if it wasn’t memorable. How could Skyrim compete with that?
So there I was, probably around 3 AM, finally deciding to track down this kid in Windhelm doing the Black Sacrament. The atmosphere was perfect—my crappy apartment heating had given out (again), so I was wrapped in blankets, shivering slightly as I navigated the already-chilly city of Windhelm. When I found Aventus Aretino performing that creepy ritual—”Sweet Mother, sweet Mother, send your child unto me…”—I got actual goosebumps. Not from the cold, but from that perfect gaming moment when immersion just clicks.
The first assassination—Grelod the Kind—seemed simple enough. Almost disappointingly so. Walk into the orphanage, kill the old lady, walk out. But it was what happened AFTER that hooked me. Waking up in that abandoned shack with Astrid watching from atop the bookshelf? That twist caught me completely off guard. I literally said “Oh shit!” out loud, startling poor Whiskers off his perch.
Astrid remains one of gaming’s most complex characters for me. Not because she’s particularly deep by literary standards, but because of how effectively the game makes you feel about her. That initial fear and respect, gradually evolving into camaraderie, and then… well, we’ll get to that betrayal. Voice actress Cindy Robinson deserves massive credit here. There’s this subtle quality to Astrid’s voice—equal parts seductive and threatening—that perfectly embodies what the Dark Brotherhood is supposed to be.
The Falkreath Sanctuary felt like coming home, which is a weird thing to say about a cave full of murderers, but it’s true. I spent an embarrassing amount of time just hanging around, listening to the conversations between members. Nazir’s dry wit, Gabriella’s dark prophecies, Veezara reminiscing about the old ways. These weren’t just quest-dispensing NPCs; they felt like colleagues. Dysfunctional, homicidal colleagues, sure, but still.
And then there’s Cicero. Freaking Cicero. I’ve never had such a love-hate relationship with a video game character. That high-pitched voice grated on my nerves something fierce at first. My roommate at the time would mockingly repeat “Let’s KILL someone!” in that voice whenever he caught me playing. But damned if the character didn’t grow on me. His absolute devotion to the Night Mother, his journal entries documenting his slow descent into madness—it’s brilliant character work.
The Cicero fate choice hit me harder than it probably should have. I had to pause the game and actually think about it. This annoying jester had betrayed the Brotherhood, but he was right, wasn’t he? Astrid HAD led them away from the old traditions. I ended up sparing him, partly because I found his loyalty admirable, partly because I couldn’t bring myself to kill the last true believer of the old ways. Also, I’d be lying if I said game mechanics didn’t factor in—that Cicero’s Outfit with its jester hat is just too unique to miss. (Though I never wear it because, c’mon, an assassin in a bright jester outfit? Not exactly stealthy.)
The Night Mother’s lore absolutely fascinated me. I went down a wiki rabbit hole for HOURS after that questline, reading about her history, the Five Tenets, how the Black Hand was organized in previous eras. There’s something deeply unsettling about climbing inside a corpse for a mission, let alone discovering she can speak directly into your mind. I may have physically recoiled from my screen during that revelation. My cat chose that exact moment to jump on my lap, and I nearly threw both him and my controller across the room.
Let’s talk about that wedding assassination—Vittoria Vici’s murder during her special day. What a setpiece. I meticulously planned my approach, scouting the area, identifying the perfect sniper position on that balcony. I quicksaved about a dozen times, determined to get it just right. When I finally triggered that loose gargoyle statue to fall and crush her mid-speech? *Chef’s kiss* Perfect cinematic moment, followed by absolute chaos. I barely escaped through the city streets, heart pounding, genuinely feeling like an elite assassin pulling off the perfect hit. Few gaming moments have made me feel so accomplished.
The mission variety throughout the questline showcases why Skyrim endures while so many other games fade from memory. One mission you’re poisoning a emperor’s body double, the next you’re infiltrating a party as a guest, then you’re arranging a tragic “accident” for a housemaid. Each hit feels distinct, with multiple approaches possible. I replayed the Gourmet assassination at least three different ways just to see all the possibilities. (Jarrin Root in the potage was definitely the most satisfying, though.)
Confession time: I’ve never been good at stealth mechanics in games. My typical approach to most games is the equivalent of kicking in the front door while dual-wielding the biggest weapons available. But something about Skyrim’s Dark Brotherhood made me want to master the art of the silent kill. I spent ages perfecting the timing of stealth arrow shots, figuring out guard patrol patterns, and mastering the backward-walking silent assassination technique. I built my character around those perfect stealth kill mechanics that trigger those brutal killcam animations. Getting that throat-slitting animation when sneaking up on a target never gets old, I don’t care how many times you’ve seen it.
The armor sets deserve special mention. The standard Dark Brotherhood armor isn’t just functionally excellent for an assassin build—it looks intimidating as hell. First time I put on that full set with its red and black color scheme, I spent a good five minutes just rotating the camera around my character, admiring it from different angles. My boyfriend at the time walked by, glanced at the screen and said, “Wow, overcompensating much?” Listen, if you’re going to be an assassin, you might as well look the part. (We broke up three months later, completely unrelated to my Skyrim fashion choices. Mostly unrelated.)
The twist with Astrid’s betrayal genuinely shocked me. I’d grown so comfortable with her leadership that when she sold me out to the Penitus Oculatus, I felt a very real sense of betrayal. Finding her burned body later, hearing her confession, being asked to kill her… man, I sat with that choice for a long time. The game does this brilliant thing where it forces you to use the Blade of Woe—her own knife—to end her suffering. The symbolism isn’t subtle, but it’s effective. I remember just sitting there after that scene, processing what had happened, while my poor neglected cat meowed for dinner.
Comparing it to Oblivion’s Brotherhood is inevitable. Oblivion had the more intricately designed individual missions, without question. That murder house puzzle box mission? Legendary. But Skyrim’s Brotherhood succeeds in creating a more complete narrative arc. You’re not just climbing the ranks—you’re witnessing and participating in the death and rebirth of an entire ancient organization. By the end, when you’re listening to the Night Mother as the Listener, sitting in the Dawnstar Sanctuary as the new leader, it feels earned in a way few game accomplishments do.
I’ve played through Skyrim more times than I care to admit. Different builds, different faction choices, different moral alignments. But I always, ALWAYS end up rejoining the Brotherhood. Something about that storyline pulls me back every time. Maybe it’s the characters, maybe it’s the moral ambiguity, or maybe it’s just that the missions are so damn satisfying to execute (pun absolutely intended).
Years later, I found myself dating someone who’d never played Skyrim (I know, I know, red flag). I insisted on watching her play through the Dark Brotherhood questline, probably ruining her experience with my running commentary. “No, don’t kill Cicero! Trust me!” and “Ooh, this part’s so good, watch this!” But seeing her reactions to the same twists and turns that had shocked me years earlier was like experiencing it all again for the first time. She jumped at all the same moments, cursed Astrid with the same vehemence, and felt the same satisfaction when finally eliminating the Emperor. We broke up a year later, but she still texts me occasionally about Skyrim. Some bonds transcend relationships, I guess.
These days, with my receding hairline and increasing responsibilities, I don’t have the luxury of marathon Skyrim sessions anymore. But every so often—usually around 1 AM when I should absolutely be sleeping instead—I’ll fire it up, create a new character, and make a beeline for Windhelm. “Sweet Mother, sweet Mother, send your child unto me…” I’ll be home soon enough.
