It’s been a very long week, so let’s just all say it again, one last time, loud for the people in the back, and get it out of our system: The rebranding of Twitter to X is dumb.

Dumb in the way that there are 44 billion reasons why intentionally tanking a globally recognized brand might not be the best strategy for building a business. But here’s the thing: It’s also dumb in ways that aren’t immediately apparent.

A rebrand is one thing; but the use of X itself, specifically, only further confounds as to why Musk chose it as the mark of “the future state of interactivity.” If you dig into the long, strange brand and marketing history of X, the stupidity has a blast radius that should give anyone pause before ever considering the 24th letter of the alphabet for marketing or branding any product or company. Maybe not “ever,” but certainly for the foreseeable future. And probably longer, just to be safe.

BEFORE 1972

More than half a century ago, Brand X had a clearly defined identity in the culture. It was the “other guy,” the one so unspeakably inferior that you dare not utter its name. X was the well-worn mystery alternative of comparative advertising: The unnamed box that brand-name deodorants, detergents, soaps, razors, and more would compare themselves to in commercials, as in “Nine out of 10 people picked Gillette razors over Brand X.” It’s a device still somehow in practice, as this recent mayo ad from the Philippines can attest.

The Federal Trade Commission thought the idea of Brand X was played out by 1972, when it convinced the TV networks to lift their ban on ads that mention competition by name. So let that sink in: The government recognized 51 years ago that X was a meaningless signifier, and the American consumer was sophisticated enough to handle something like the Pepsi Challenge (which kicked off just a few years later, in 1975). X was dead, or so one might have thought.

THE PORN YEARS

Of course, X actually had one home in the early 1970s. The X rating, originally classified in 1968 by the Motion Picture Association of America (MPAA), was for any film deemed only suitable for adults. Initially, it applied to challenging films as diverse as the Oscar winner, Midnight Cowboy, and cult classic A Clockwork Orange. It also became affixed to the first mainstream pornography movies distributed in theaters at that time. With the early success of X-rated titles, porn distributors then got increasingly creative, trying to entice audiences with completely fictional and exaggerated adaptations of the rating, such as XX and XXX.

This led to confusion and ultimately, the decline in broader popularity of anything remotely associated with X by the mid-1970s. As a certain billionaire might reply online, interesting: X became so degraded that even the most boundary-pushing filmmakers did whatever they could to make sure their films qualified for the more palatable R-rating. The MPAA rebranded X as NC-17 in 1990.

THE EIGHTIES

The late 1970s saw the formation and popularity of two punk bands, the U.K.’s Generation X, and Los Angeles-based X, both of which tapped into whatever mystery and danger was left in the letter. Generation X didn’t last more than a few years and broke up by 1979 while X’s best, most critically acclaimed album, Los Angeles, debuted in 1981.

In the corporate world, troubled brands that had stagnated in the face of nimbler competition began circling the letter X to convey innovation. Take General Motors’ X-car project, for example, which officially launched in 1979. The bold, new car design concept straddled a SuperFriends-esque spectrum of GM models and brands––the Chevy Citation, Buick Skylark, Pontiac Phoenix, and Oldsmobile Omega—and aimed to fundamentally change the automotive landscape. The X-car family, though, was plagued with just about any and every production and performance issue possible, and instead ended up standing for catastrophic failure.

THE NINETIES

Douglas Coupland’s 1991 best-seller Generation X went a long way to help define the generation overshadowed by the baby boomers. Coupland told the Boston Globe at the time that part of the novel’s goal was to show how people born after 1960 think about things differently than boomers. “We’re sick of stupid labels, we’re sick of being marginalized in lousy jobs, and we’re tired of hearing about ourselves from others,” he said. There’s even a chapter called “I Am Not A Target Market.”

Spoiler alert: Brands and advertisers believed otherwise.

By 1995, the growing popularity of action sports such as skateboarding and BMX biking gave rise to ESPN’s Extreme Games, which was quickly shortened to the X-Games. Brands did not want to miss out on the adrenaline-pumped popularity of Tony Hawk, so culture was inundated with all things X. To live truly on the edge, you need to shave with Schick Xtreme shaving foam. And why use regular deodorant when you can slap some Right Guard Xtreme on those pits?

This X-inspired lifestyle hit the road in 1999 when Nissan launched its Xterra SUV, aimed at people who rode rapids on bodyboards and mountains on off-road skateboards. Then it was gaming in 2001 when Microsoft launched the Xbox.

By then, likely thanks to eXtreme overexposure, the shine on names with X had begun to dull, as even Microsoft’s marketing department had only been using that name as a placeholder (until focus groups told them otherwise). Five years later, given its desperation to appear cool in the shadow of Apple’s iPod, it’s a minor miracle Microsoft didn’t name its MP3 player the Xune.

Imagine the effect on an ambitious twentysomething in that moment, when every company wanted to reach you but was being told you’re simply unreachable. If only there were a secret symbol you could flash that this company gets you, so you know, give us all your money.

ELON’S FIRST X (1999-2000)

After he sold his first startup, the online city guide Zip2, to Compaq for $307 million in 1999, Musk founded an internet financial superstore that he dubbed X.com. It aimed to be an all-in-one online bank, mortgage and insurance broker, and mutual fund company. Part of the company’s marketing was to pay people for referring new customers with $20 and $10 cash cards. Sound familiar?

However, X.com eventually was forced to merge with PayPal, which then led to a brand tug-of-war to decide which name the new company would be known by. Investors wanted to stick to online payments, but Musk was determined to keep pushing for what today we might call his “everything app” version of X. It was a fixation that inevitably led to his infamous 2000 ousting from the company. PayPal, as it would be known, would go on to sell to eBay for $1.5 billion in 2002 (the same year Vin Diesel tried—and failed—to make spy movies xtreme with XXX).

Before the PayPal merger, Musk sat down with a writer from an online magazine to discuss his ambitions. The reporter asked him about the company name. “You know the ads for Tide, where there’s a name brand and brand X, and brand X always loses? Well, our ads can be like that except that brand X wins.”

Twenty-four years later, Musk doesn’t believe in advertising, and Brand X has yet to score a big win. But hey, X springs eternal.