Segways. Like many technologies on this list, the Segway has had a surprisingly long career as a goofy gadget. When it debuted in 2001, it seemed like a wildly expensive solution to a problem that didn’t exist: how can we walk without actually moving our legs? It immediately became a punchline, but then, as the years went by, the joke just kept getting better: Segways started persistently appearing in inherently funny situations. Mall cops ride them. Tourists ride them like ducks in a row. When Jimi Heselden, owner of Segway, Inc., died in 2010 after riding a Segway off a cliff, the personal transportation device’s first decade of ridiculous existence was capped in macabre fashion.

Meat tenderizers. A.K.A. the vicious-looking toothed hammers our grandmothers pull from their kitchen drawers at schnitzel time.

E-cigarettes. Except for the fact that young children have died by drinking e-cigarette fluid (a danger that the New York Times editorial board has embarked upon an oddly extended crusade to eliminate), everything about e-cigs is funny. First, the fact that they work like stage cigarettes, so that everyone who smokes them looks like they should be wearing pancake makeup and reciting dialogue from Shaw. Then there’s the fact that people who smoke them seem to universally hate being seen with them—let’s be honest, real smoking has never stopped looking cool, so people who turn to e-cigs seem to feel like they’ve made a Faustian bargain where they’ve saved their lives but lost their souls. Finally, there’s the name: e-cigs. The “e” preface is associated with all the least fun aspects of the information age: e-mail, e-commerce, e-tickets. An iCig would be even worse, though, because you know who would be smoking it? Bono.

Blimps. The blimp is the mascot of air transportation. With whatever genuine utility they might have had now eclipsed by helicopters and drones, blimps are pretty much just good for blimping around looking blimpy. Even funnier—though in a darker way—are blimps’ more serious-minded cousins, the zeppelins.

21st-century razors. Inspiration for the most prophetic Onion headline of all time, “Fuck Everything, We’re Doing Five Blades.” Having reached the limit of meaningful technological innovation in blades that scrape across your body to remove hair—and having gendered its razors to the point of absurdity—Gillette has moved to incorporating virtually meaningless features like “FlexBall technology,” a “microcomb,” a “lubrastrip,” and “re-engineered blades.” Though 927 online reviewers give 4.49 out of 5.00 to the Fusion® ProGlide®, I’ll personally stick with my Fusion® Power. How can a razor be the best a man can get™ without battery-powered Micropulses?

Velcro. Like a lot of inherently funny technologies, velcro seems like something Jules Verne might have envisioned, but that we haven’t actually figured out how to really make, so we kind of half-ass it. It’s like, okay, we don’t know how to make actual self-sealing clothing fasteners, so how about if we just take a patch of little loops of string and then take a patch of little hooks and smash them together? Probably a lot of the hooks will catch on the little loops, and that will be good enough. Yeah, the loops will eventually tear, and the hooks will accumulate other crap, and we’ll just have these useless patches on jackets and shoes that we can only close because, knowing the velcro would fail, the designer additionally added zippers and/or laces to—but for like the first few days, it’ll be great.

Whammy bars. In 1935, Doc Kauffman patented the Kauffman Vibrola, the first vibrato system for guitar, thus ensuring that ambitious soloists for decades to come would sound incredibly fierce while looking like they’re jiggling a toilet handle.

Microsoft products. Apple had the first graphical user interface, and Microsoft has never quite managed to pull Windows off as smoothly as Apple does. Windows releases are delayed, they’re buggy, they’re virus-prone. They want a song about starting a computer, so they pay the Rolling Stones an infinite amount of money to use “Start Me Up.” Microsoft products are built to be punchlines, and that doesn’t just go for Windows: it also goes for products like MSN Messenger, which answered AOL’s yellow running mascot with two round blue figures—having only little heads and fat bodies without feature or limbs—cozied up to each other. On Windows phones, the variable-size icons just make it look like you’re showing off. (“Look, I have e-mail!”) And then there was Zune.

iPads. This is where Apple inspires its own guffaws: first for the name, which still seems poorly considered, and then for the fact that these tablets show up in all the dorkiest places. Whereas it was the coolest people you knew who had the first iPhones, and it’s the talk-show host with the Roots for his house band who conspicuously plants a MacBook on his desk, it’s your mom who takes her iPad to the Paul McCartney concert to take photos with it. You also see iPads in museums that think the best way to interact with 21st century visitors is to put the exhibit labels on screens instead of placards and at coffee shops that sustainably source the wood for their handcrafted tablet cradles, then check you out on Square with suggested tip levels of 20%, 30%, and 40%. When Justin Timberlake showed up noodling around on an iPad in his “Suit & Tie” video, sexy immediately went back to wherever he’d originally brought it from.

VCRs. Some might struggle with their DVRs the way they once did with their VHS machines, but the DVR will never be the magnificent standing joke that was the VCR, a once-expensive appliance that would sit front and center in the living room for decades, flashing 12:00 again and again as a testament to their owners’ incompetence.

– Jay Gabler

Image credits: Segways courtesy Segway; meat tenderizer via Wikimedia Commons; e-cigs courtesy Blu; blimps via Wikimedia Commons; razor courtesy Gillette; Velcro by Dave (Creative Commons); whammy bar by irish10567 (Creative Commons); Windows 95 screencap; iPad courtesy Apple; VCR ad by Sony