Man, I’ve got to tell you about the time Skyrim made me care more about fictional assassins than I probably should have. This was back in 2011 – November 11th to be exact, because yeah, I’m that kind of nerd who remembers launch dates. I’d taken the day off from teaching, told the principal I had “family obligations.” Which wasn’t technically a lie since my Sega Genesis counts as family, right?
I’d been avoiding Bethesda games for years, honestly. After Sega died and I watched everyone praise games that weren’t made by my beloved company, I got pretty bitter about the whole industry. But my wife kept nagging me to try Skyrim. “It’s different,” she said. “You’ll like the freedom.” I grumbled about it for weeks before finally caving, mostly because she threatened to hide my Saturn games if I didn’t give it a shot.
So there I was, probably three days into this massive time sink, wandering around Windhelm when I stumbled across this kid doing some seriously creepy ritual. Aventus Aretino, chanting “Sweet Mother, sweet Mother, send your child unto me” over and over. Now, I teach high schoolers all day – I know creepy when I see it – and this was weapons-grade unsettling. But something about it hooked me immediately. Maybe it was the voice acting, maybe it was the atmosphere, but I knew I was about to go down a rabbit hole.
The whole Grelod the Kind assassination seemed straightforward enough. Walk into Honorhall Orphanage, eliminate the abusive headmistress, walk out. Basic stuff. I’d played enough Sega CD FMV games with terrible acting to appreciate good storytelling when I saw it, and this felt different. More personal, somehow. When I actually went through with killing her – and yeah, I felt weirdly guilty about it even though she was obviously terrible – I figured that was it. Quest complete, moving on.
Then I woke up in that shack with Astrid perched above me like some kind of leather-clad spider, and everything changed. That moment when she’s testing you, making you choose which captive to kill? I actually paused the game and walked around my house for ten minutes trying to decide. My wife asked what was wrong and I tried explaining that a video game was making me question my moral compass. She just rolled her eyes and went back to grading papers.
Astrid became this fascinating character for me – not because she was complex in some literary sense, but because she represented everything I’d been missing in games. She had actual personality, motivations that made sense, dialogue that didn’t sound like it was written by committee. Cindy Robinson’s voice work was incredible; she managed to make Astrid sound dangerous and charismatic simultaneously. After years of listening to terrible Sega CD voice acting, I could appreciate the craft that went into this performance.
The Falkreath Sanctuary felt more welcoming than it had any right to. Here’s this underground cave full of professional killers, and somehow Bethesda made it feel like a clubhouse. I’d spend way too much time just hanging around listening to conversations between Nazir, Gabriella, and Veezara. These weren’t just NPCs waiting to hand out quests – they felt like actual people with histories and relationships. Coming from someone who’d watched Sega struggle with narrative for years, this was revelatory.
Then there’s Cicero. Oh man, Cicero. That voice grated on my nerves worse than nails on a chalkboard initially. My teenage daughter would mock me by repeating his lines whenever she caught me playing: “Let’s kill someone!” in that high-pitched sing-song voice. But the more I learned about his backstory – his journal entries documenting his slow descent into madness, his absolute devotion to the Night Mother – the more I appreciated what the writers were doing. This wasn’t just comic relief; this was a character study in fanaticism and loyalty.
When it came time to decide Cicero’s fate after his betrayal, I actually had to save and quit for the night. Couldn’t make the choice. See, he’d betrayed Astrid and the Brotherhood, but he was right about them abandoning the old ways. As someone who’d watched Sega abandon everything that made them special in pursuit of mainstream appeal, I understood his position. I ended up sparing him, partly out of respect for his convictions, partly because that Jester’s Outfit was too unique to lose. Though I never actually wore it – kind of defeats the purpose of stealth when you’re dressed like a carnival act.
The Night Mother mythology absolutely fascinated me. I went down a Wikipedia rabbit hole that lasted until 3 AM, reading about the Five Tenets, the Black Hand organization, all the lore from previous games. There’s something deeply unsettling about climbing inside a centuries-old corpse, let alone having that corpse start giving you missions telepathically. I may have physically recoiled from my monitor the first time she spoke directly to me. Scared the hell out of my cat, who was sleeping on my desk.
That wedding assassination – Vittoria Vici’s public execution – remains one of my favorite gaming moments ever. I spent an embarrassing amount of time planning the perfect approach, quicksaving and reloading to scout different angles. When I finally positioned myself on that balcony and triggered the gargoyle to fall during her speech? Pure cinematic gold. The chaos that followed, escaping through Solitude’s streets while guards searched everywhere – I felt like a master assassin pulling off the perfect hit. Few games have ever made me feel that accomplished.
What impressed me most was the mission variety. One job you’re poisoning the Emperor’s body double, the next you’re infiltrating a party, then you’re arranging an “accident” for a maid. Each hit felt distinct, with multiple solutions possible. I replayed several missions just to see different approaches work. The Gourmet assassination alone had me experimenting for hours – though nothing beat the satisfaction of slipping Jarrin Root into that soup and watching the results.
I’ve never been great at stealth in games, honestly. My usual approach is more “kick down the door with the biggest weapon available” – probably influenced by years of Sega Genesis action games where subtlety wasn’t really an option. But something about the Dark Brotherhood made me want to master the art of silent killing. I spent countless hours perfecting stealth archery, learning guard patterns, figuring out those brutal stealth kill animations. Getting that throat-slitting killcam never got old, no matter how many times I’d seen it.
The armor sets deserve mention too. That standard Dark Brotherhood gear isn’t just functionally perfect for stealth builds – it looks intimidating as hell. First time I equipped the full set with its red and black design, I spent way too long just rotating the camera, admiring how badass my character looked. My son walked by, glanced at the screen, and said “Dad, you’re such a nerd.” Yeah kid, guilty as charged.
Astrid’s betrayal hit me harder than it should have. I’d grown comfortable with her leadership, trusted her judgment, so when she sold me out to the Penitus Oculatus, I felt genuinely betrayed. Finding her later, burned and dying, asking me to end her suffering with her own blade – that scene stuck with me for days. The symbolism wasn’t subtle, but it was effective. I remember sitting there after killing her, processing what had happened while my neglected dinner got cold.
Comparing it to Oblivion’s Dark Brotherhood is inevitable, I guess. Oblivion had more elaborate individual missions – that murder party where you had to eliminate everyone without being detected was legendary. But Skyrim’s Brotherhood succeeds as a complete narrative. You’re not just climbing ranks; you’re witnessing the death and rebirth of an ancient organization. By the end, when you’re the Listener sitting in the rebuilt Dawnstar Sanctuary, it feels earned in a way most game achievements don’t.
I’ve replayed Skyrim more times than I care to admit. Different builds, different choices, different moral alignments. But I always end up rejoining the Brotherhood eventually. Something about that questline keeps pulling me back. Maybe it’s the characters, maybe the moral ambiguity, or maybe it’s just that the missions are so damn satisfying to execute.
These days, with teaching responsibilities and teenagers who think I’m hopelessly uncool, I don’t get those marathon gaming sessions anymore. But every few months, usually late at night when I should be grading papers instead, I’ll fire up Skyrim and head straight for Windhelm. “Sweet Mother, sweet Mother, send your child unto me…” And just like that, I’m home again.
Joe’s a history teacher who treats the console wars like actual history. A lifelong Sega devotee from Phoenix, he writes with passion, humor, and lingering heartbreak over the Dreamcast. Expect strong opinions, bad puns, and plenty of “blast processing.”
