Old Portland, Maine Craigslist Ad Named the Internet’s ‘Funniest’

Sometimes it’s remarkable to think how long Craigslist has been around giving us access to the best and worst classifieds straight from the internet. At one point Craigslist was truly the Wild West where seemingly anything and everything went unchecked. In recent years, Craigslist has tightened things up a bit, leaving fewer ridiculous and offensive ads for people to see. But that doesn’t mean people haven’t kept receipts from past years.

Shared by Techblog, they dug through thousands of old Craigslist ads and compiled a list of 5 they deemed the “funniest” of all time. An announcement from Portland, Maine didn’t necessarily make the list, but it topped it. And if we really peel back the layers of that remarkable Meghan ad from 2007, it only gets funnier.

via Techblog

via Techblog

First of all, whoever Meghan is, she’s absolutely an expert with words. She could probably sell you a 2012 Ford Focus with a transmission problem at the 2022 BMW price. She also had a deep understanding of supply and demand. Good luck finding yourself a pack of Stride Fruit Gums Forever these days and Meghan clearly understood that the future was bleak for the niche brand and there was money to be made. Even if it was only 9 cents. There’s also a touch of business savvy to his game, essentially demanding exact change without absolutely demanding exact change.

Is this really the “funniest” Craigslist ad ever? Probably not. Wish there were more announcements like this these days? Yeah.

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