The youth culture of the early 2000s didn’t produce any artists worth remembering, but we did make two really good brands, Vice and American Apparel. Those companies are us: antiauthoritarian capitalists obsessed with being cool and monetizing that coolness. While Vice is doing fine (with $400 million in the bank from Disney on a valuation of $4 billion), American Apparel is going out of business, more or less, bought last week by Canadian company Gildan Activewear, who will be closing all of its stores and famous Los Angeles factory. At a Manhattan location, staff said they could be closed by April. It’s the final chapter of a long decline.

How did American Apparel go from being worth a billion dollars just a few years ago, with 10,000 employees and about as many stores as J. Crew, to the trash heap of history? How did Vice succeed where its sister brand failed, especially because, honestly, American Apparel was always the cooler one?

American Apparel was so essential to the culture that its ads and corporate arc were covered closely everywhere from Gawker to the New York TimesObserver once wrote a trend piece about people hanging around on a bench outside its Lower East Side location. That story is full of lines like, “The Bench [note the capitalization!] has been going on for almost two months, attracting everyone from hip-hop D.J.’s (like A-Trak, Kanye West’s turntablist) to trash-talking graffiti artists to modelesque party girls to school teachers,” which sounds corny except that it was all true. Am Appy (an extremely useful shorthand coined by Hipster Runoff) was part of the hip-hop world, the fine art world, and more. It was dirtbag Versace.

Rewind to 2007 or so, and you’ll find both American Apparel and Vice at the heart of youth culture. And you didn’t have to do too much looking, really, because they were probably in the same place: an American Apparel ad was almost always on the back cover of Vice, a magazine which you could always find in a pile somewhere in an American Apparel store. That back cover was the primary canvas where American Apparel painted its brand with their famously seedy, problematic, and impossibly sexual ads, to the benefit of both brands.

Those ads! In the company’s heyday, there was always one on a billboard at the corner of Chrystie and Houston, stretching a full half-block, a different beautiful woman staring out at you every few months when you got off the 2nd Ave stop on the F. The company was famously obsessed with casting real women, and putting up unphotoshopped photos of them. In 2008 or 2009, walking down Houston turning your gaze down from the billboard to the people walking by you on the street, it was impossible to deny that American Apparel very much knew its target audience.

Those ads, which usually featured a woman in her twenties, barely clothed, staring directly into the camera as if she were about to start making out with it, have been called pornographic. As we found out later, that was truer than we could have guessed. Many of them were taken by the celebrity photographer Terry Richardson with his dick already out of his pants and waving in the face of the model, often allegedly without that model’s consent.

Pick any given issue of Vice, and Richardson probably shot both one of those ads and a different hyper-sexual picture for the magazine’s actual cover. While hipsters of the time sneered at the Jessica Simpson, Maxim magazine culture dominating most of America, in truth, Vice was our Maxim, full of naked women and dumb stunts and interns forced to drink their own urine (and maybe their boss’s, too).

It was the same at American Apparel’s online store, as much a porn site as a online commerce portal for buying clothing—they once ran a best butt contest where fans were encouraged to send in pictures of their butts in the kind of harsh flash porno-Polaroid style that was popular at the time. They seemed to get thousands of entries and ran almost every single one of them on the site in endless photo galleries (hard to imagine from J. Crew).

When the company ran into trouble, they stopped using women on their iconic LES billboard and changed to a picture of Woody Allen dressed like a Hassid, a still from Annie Hall, which stayed for years. I always wondered how they’d gotten permission to use that, and turned out they hadn’t. Woody Allen sued Am Appy, who eventually settled for $5 million.

During this time Vice was fine, but nothing to get particularly excited about. Their parties were legendary in the early days for being full of cocaine, and in the later days for being a place you went to wait in line for hours before the cops showed up to shut everything down right as you were about to get in.

But there was always something a little try-hardy about all this. There’s a reason frat guys and stock brokers have a reputation for being so hard-partying: only boring people make a big show about how crazy they are.

American Apparel, man, they were for real, as personified in their founder, Dov Charney.

If Charney built the company by being totally open to the darkly sexual zeitgeist of the time—2011’s Sucker Punch is an $83 million movie about girls in bras getting sexually and physically abused while murdering cartoon monsters—he was also destroyed by it. He couldn’t keep his dick in his pants through a 20-minute interview, let alone at work all day. He allegedly sexually harassed almost every female employee of the company, which led to him getting himself fired from the business he founded and personified.

The rejection of the world of Am Appy has been as central to our culture as its popularity was. A 2010 article on The Gloss by Jaime Peck about her experience being sexually abused by Richardson while working as a model was arguably the first major piece of the kind of online feminist writing that’s come to dominate discourse in certain parts of the internet. For years afterwards, pieces about the place of women in pop culture and pop art tended to focus on Richardson and Charney, because they were such gleefully open scumbags behaving so badly, so frequently. Eventually, Richardson became something of an art-world pariah (though he still gets plenty of work), and Charney was exiled from Am Appy.

Vice, meanwhile, like all businessmen with a drug habit, just cleaned themselves up a little and became fabulously successful. With its cable channel and HBO shows, Vice is more successful than most, holding a current valuation of around $4 billion.

Am Appy, on the other hand, is going out of business. It’s a shame, because, honestly they made some good clothes. I really like their sweatshirts.