The early 2010s were a weird, lawless time on the internet. Before everything became a polished, corporate algorithmic feed, we had blogs. And one of the biggest, most chaotic blogs to ever grace a browser window was Emails From An Asshole.
It’s hard to explain the specific brand of joy this site brought. Basically, a guy named John Lindsay would find ridiculous, low-stakes ads on Craigslist—people selling a used "soul," or looking for a "vampire hunter"—and he’d respond to them. He wasn't just being mean for the sake of it. He was a performance artist of the absurd. He played a character that was aggressively difficult, taking every word literally and dragging people into deep, nonsensical arguments over nothing.
People still search for it today because it feels like a time capsule of a more authentic, albeit cruder, internet.
The Genius Behind the Madness
John Lindsay wasn't just some random troll. He was the architect of Don't Even Reply, the official title of the site that hosted these Emails From An Asshole. He had this uncanny ability to spot the exact person who would be most easily rattled by a confusing response.
Think about the "Hidden Camera in a Clock" exchange. Someone was trying to sell a clock with a spy camera in it. Lindsay replied pretending to be a paranoid husband who wanted to hide it in a bathroom. When the seller got uncomfortable, Lindsay doubled down, acting like the seller was the weird one for questioning him. It was a masterclass in gaslighting for comedic effect. He made the "straight man" in the conversation look ridiculous just by holding up a mirror to the weirdness of Craigslist itself.
The site blew up. It was so popular it eventually turned into a book, Don't Even Reply: The Emails from an Asshole, published by Gotham in 2011. You've probably seen similar stuff from David Thorne—the "Seven Legged Spider" guy—but Lindsay’s work felt grittier. It felt like he was actually talking to the strange neighbors you didn't want to meet.
✨ Don't miss: Death Wish II: Why This Sleazy Sequel Still Triggers People Today
Why We Crave This Kind of Content Now
Internet humor has changed. Everything is a TikTok sound or a highly edited "prank" video that’s usually fake anyway. Emails From An Asshole worked because it was static. You had to read it. You had to imagine the frustration on the other side of the screen.
There’s a certain psychological itch that these emails scratch. It’s the "call of the void" but for social interactions. We’ve all wanted to reply to a delusional Facebook Marketplace listing with something snarky, but we don't. Lindsay did. He was the surrogate for everyone who has ever looked at a "No Lowballers" ad for a rusted 1998 Honda Civic and wanted to offer a trade for a half-eaten sandwich and a handful of magic beans.
Honestly, the site also succeeded because of its simplicity. No flashy graphics. Just white text on a black background, screenshots of the original ad, and then the transcript of the ensuing disaster. It felt like you were looking at something you weren't supposed to see.
The Anatomy of a Classic Interaction
- The Hook: Lindsay finds an ad that is either too demanding, legally questionable, or just plain stupid.
- The Initial Bait: He sends a reply that seems semi-normal but has one glaring red flag or weird request.
- The Escalation: Once the seller replies, he pivots. He becomes the "asshole."
- The Fallout: The seller eventually realizes they are talking to a brick wall or a lunatic and stops replying, usually after a flurry of all-caps insults.
Take the "Construction Worker" email. A guy was looking for help with a home renovation. Lindsay replied pretending to be a professional but kept insisting that he would only work if he could bring his "pet" (which was actually a wild animal) and if he could take frequent naps in the owner's bed. The sheer audacity of the requests is what makes it work. It’s not just "being a jerk." It’s a creative deconstruction of social norms.
The Ethical Gray Area (and the Backlash)
Not everyone thinks Emails From An Asshole is funny. There’s a valid argument that it’s just bullying. In a world that’s increasingly focused on empathy and digital wellness, the idea of "trolling" people who are just trying to sell a lawnmower feels a bit dated. Some of the people he messaged were clearly struggling or just not tech-savvy.
🔗 Read more: Dark Reign Fantastic Four: Why This Weirdly Political Comic Still Holds Up
However, Lindsay often targeted the "big shots"—people who were being arrogant, sexist, or trying to scam others. In those cases, the emails felt like a weird form of vigilante justice. If you’re trying to sell a "haunted" item for $500, maybe you deserve to have your time wasted by a guy asking if the ghost likes Cheetos.
It’s also worth noting that the internet in 2010 was much smaller. The stakes felt lower. Today, if you do this, you might get "doxxed" or lose your job. Back then, it was just a funny blog post that lived in its own little corner of the web.
The Legacy of Don't Even Reply
Why does this still matter in 2026? Because it influenced an entire generation of digital comedy. You can see the DNA of Emails From An Asshole in everything from "scambaiting" YouTube channels to the way brands interact with each other on X (formerly Twitter).
It taught us that the most powerful tool in an argument isn't logic; it's absurdity. If you refuse to play by the rules of the conversation, the other person has no power over you. It’s a terrifying and hilarious realization.
While the site hasn't been updated in years—and the original "asshole" has largely moved on from the project—the archives remain a gold mine for anyone who misses the "Wild West" era of the internet. It’s a reminder that before there were influencers, there were just people with way too much time on their hands and a Gmail account.
💡 You might also like: Cuatro estaciones en la Habana: Why this Noir Masterpiece is Still the Best Way to See Cuba
How to Revisit the Chaos Safely
If you’re looking to dive back into the archives, here’s how to do it without getting lost in the weeds of modern copycat sites.
- Check the Internet Archive: The original Don't Even Reply site can be finicky. The Wayback Machine is your friend if you want to see the original layout from 2009-2012.
- Look for the Book: The physical book actually contains some "lost" emails that weren't on the site. It’s a rare instance where the print version of a blog is actually worth owning.
- Read the "Vampire Hunter" Thread: If you only read one, make it that one. It’s the quintessential example of the format.
- Observe the Pattern: Notice how he never breaks character. That’s the key. The moment you wink at the camera, the joke dies.
Actionable Takeaways for Modern Communicators
While you probably shouldn't go around being an "asshole" in real emails (unless you want to get fired), there are some weirdly practical lessons here:
- Take things less seriously. Most "urgent" emails aren't.
- Precision matters. Lindsay’s jokes worked because he picked up on specific words and twisted them.
- Sometimes, not replying is the best move. The people who "lost" in these emails were the ones who kept engaging long after it was clear the conversation was insane.
- The power of "No." Lindsay’s character was great at saying no to reasonable requests and yes to insane ones. It’s a reminder that you own your digital space.
Go find the "Disc Jockey" exchange. Read it. Then, the next time someone sends you an annoying email, just remember: you have the power to be the most difficult person in the world, even if you choose not to be. That knowledge is a gift.
Next Steps for the Nostalgic:
Start by visiting the archived version of the "Construction Job" thread to see the height of Lindsay's absurdity. If you're a writer, analyze his use of "the straight man" dynamic to improve your own comedic timing in prose. Finally, if you're looking for modern equivalents, check out the "scambaiting" community on Reddit, which carries the torch of wasting the time of those who deserve it most.