Having a Cow, Man

From knockoff Bart Simpsons to CafePress ripoffs, what the long association between T-shirts and bootlegging tells us about copyright.

By Ernie Smith

Today in Tedium: Around this time three decades ago, you could not go anywhere and not see a shirt featuring some variation of Bart Simpson on the front of it. These variations were everywhere, to the point that they inspired mainstream hip-hop culture in a significant way. Many of these bootleg shirts were parodies that emerged on the market in large part as something of a reaction to the fact that Simpsons gear was everywhere in 1990, having benefited from an early example of the Streisand effect because of school administrators who couldn’t get behind Bart’s cavalier attitude and tried getting him banned from schools. (Oh, how small that controversy feels now.) Bart bootlegs were everywhere then … and they’re far from the only example of the awkward meeting of trademark and casual wear. Today’s Tedium talks bootleg T-shirts, in all their forms. — Ernie @ Tedium

Today’s GIF comes from a 1990 news report on the Bart Simpson T-shirt controversy. These particular shirts are legit.

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“The Beatle promotion is a highly specialized one. The primary sales appeal is not the garment itself but the name and the garish autographed pictures of the Beatles which are blazoned on them. The department stores and other retail outlets purchasing these goods are plainly exploiting the Beatle craze. The market is limited to teenagers infected with the craze. No one else is likely to be interested in this merchandise. It is unlikely that those purchasing Beatle goods would consider other garments as a substitute for them or vice versa.”

— A passage from a 1964 federal court ruling in Puritan Sportswear Corp. v. Puritan Fashions Corp., a lawsuit that basically dealt with the fact that Puritan Fashions had become the exclusive authorized licensee producing T-shirts and other clothing featuring The Beatles. (Examples of their products can be seen here.) Puritan Sportswear, a similarly named clothing maker that otherwise had no overlap with its competitor, had sued to get them to stop, essentially because they were afraid that an association with rock music was going to cost them sales. Judge Frederick van Pelt Bryan, while clearly not a fan of The Beatles, also thought Puritan Sportswear’s argument was ridiculous. (Bryan was also involved in the court decision that ended the ban on Lady Chatterley’s Lover in the United States.)

Radiohead Merch Table

The merch table at a 2008 Radiohead concert. Turns out that In Rainbows’ name-your-own-price strategy did not extend to the T-shirts. (Marcela Cisneros/Flickr)

Why T-shirts are such easy targets for bootlegging

In the late 1970s and early 1980s, some of the biggest rock stars in the world had a massive problem.

Basically, they would go on tour, show up in the largest venue in a given metropolitan area with a cargo van full of T-shirts and other merchandise … and find that some jackass in town had already beat them to the punch.

For bands like Aerosmith and The Rolling Stones, this was as big a headache as Napster was for Metallica two decades later. It got so bad that the management company for many of the era’s big bands, Leber-Krebs, along with a major manufacturer of the shirts, Winterland Productions, actually went to the trouble of trying to sue the T-shirt hawkers out of existence.

A 1980 article on the problem, originally published in Rolling Stone, had this choice quote from Bruce Palley, Leber-Krebs’ director of financial affairs: “T-shirt bootleggers are like a pack of maggots. It’s not unusual to have several hundred show up for a big concert. Bootlegging is a phenomenal problem.”

Philadelphia was seen as a particular hotspot for bootleg tees. As Billboard noted in a 1978 article, the management company actually went to the trouble of hiring private investigators before a Fleetwood Mac concert at JFK Stadium, an endeavor that led to the arrest of 60 bootleg vendors at that show alone.

A promotional video for Winterland Productions from the 1980s.

Of course, Winterland Productions put in a lot of the work to get to make the shirts for all these bands—they had a right to be salty.

The problem was, Winterland ultimately had many of the same tools as their bootleg competitors. While T-shirts aren’t necessarily cheap—a significant portion of the margins go into raw materials such as fabric and screen printing—they can be easily undercut by people who are willing to cut corners, and they become far cheaper at scale.

That’s because the process of making a shirt isn’t terribly complex if you know what you’re doing. It’s more a hustle sport.

Screen Printing

An example of what screen printing looks like. (uhwestoahu/Flickr)

Screen-printing, as a concept, has roots that go back more than a thousand years, to the Song Dynasty in China, when human hair was used to carefully spread ink onto a wooden frame, and pushed across with a leaf. Later, Japan gained access to this technique, replacing the human hair with silk.

But in the modern day, the technique has evolved into something fully synthetic and simple to do. The parts are relatively cheap, and now completely synthetic—one fundamental part of screen printing today is plastisol, a synthetic ink that can be easily molded and hardened onto fabric.

All of this means that people without a lot of resources can use it to make some quick money.

A 2015 Grantland piece highlights the potential of what a well-timed screen-printing operation can do. Around the exact same time that a Northeastern University dropout named Shawn Fanning was putting the finishing touches on Napster, a student at the same school named Ray LeMoine was recruiting friends from Boston’s hardcore scene to make and sell shirts around Fenway Park. What did the shirts say? “Yankees Suck,” of course.

Did the sellers ask whether they could use the Yankees name, or get the OK from Fenway Park to start selling? Of course not, at least not at first. (Not that they needed an OK from the Yankees; it wasn’t like they were using their logo or anything.) In fact, as writer Luke O’Neil explained in Esquire in 2017, “the crew essentially operated like a drug operation, including some of the attendant violence.”

Yankees Suck Shirt

Yankees suck shirts were everywhere in the Boston area in the early 2000s. (Linson Naval/Flickr)

And given the number of shirts they were selling, the punks benefited greatly from economies of scale.

“The profits were better than drugs,” LeMoine told O’Neil. “You’re not making a $9 profit of a $10 bag of weed. I was never really a big drug dealer because the profits weren’t that good. But by the end everyone was investing their money in drugs because you can’t put cash into a bank.”

In a lot of ways, the very profitable model of bootlegging LeMoine had landed upon was basically the same as what people were doing at rock concerts in the 1970s and 1980s. In fact, it was still going on in the 2000s—around the time “Yankees Suck” had become a wearable meme around Boston, a pre-breakup Destiny’s Child was suing the same kinds of bootleggers major rock bands dealt with two decades prior.

“To record their concerts and share concerts among fans is one thing because they know you’re still going to buy their CDs,” said the group’s trademark lawyer, Kelly Tillery, in comments to Bloomberg. “The last thing you want is someone who is unauthorized and who is not paying you a royalty selling merchandise bearing your likeness.”

These days, nobody is going to shows, and when they could, often fans of a music act could actually buy shirts before going to the shows, thanks to the internet. But on the other hand, the internet age complicates the bootlegging equation significantly.


The year that CafePress, a website that allows users to upload their own shirt and poster designs, first launched. CafePress was notably a first mover in this space—I remember well that their quality control was not the greatest at first, in part because they used digital printing processes—but they grew over the years to build one of the internet’s most important models, one mimicked by Zazzle, RedBubble, and others. These shirt-makers, while popular, have in many ways worsened the counterfeiting problem in the digital age.

Mario Sonic

I own this shirt and I’m proud of it.

How the internet complicated the bootleg T-shirt problem

Buying a shirt on a website in 2020 is an interesting experience, because quite often there’s a strange mixture of fan art and parody going on that clearly riffs off of iconic pieces of pop culture but often adds something interesting and significant to them.

For example, one of my favorite recent finds on Woot’s T-shirt vertical was this fairly epic design of Mario, in a design clearly inspired by the Super Mario Bros 3. box art, dressed up in a suit that looks like Sonic the Hedgehog—riffing off the unusual suits that Mario wore in that game. Clearly, some creative license was taken with two separate properties known and loved by video game fans the world over—and it’s clearly an extension of the same point of inspiration that turned Bart Simpson parodies into torso trophies during the summer of 1990.

But what happens when the artwork isn’t really a parody or a clever creative work of its own, but a direct ripoff?

That’s a problem that has long plagued custom printing firms, though the goal, at least at for some of these firms, has been to build a manufacturing apparatus that can’t be easily outsourced.

Cafepress Factory

A CafePress factory in Louisville, Kentucky, circa 2013. (via BusinessWire)

Bob Marino, the longtime CEO of CafePress who retired in 2014, argued in Anthony Flynn and Emily Flynn Vencat’s 2012 book Custom Nation: Why Customization Is the Future of Business and How to Profit From It that custom products would be no less than “the way the U.S. manufacturing world reinvents itself.”

The reason? Simply put, there is no way to mass-produce custom swag remotely, meaning that the manufacturing process has to be bespoke, too.

“You can’t possibly save enough in labor to offset the shipping costs to get to the other side of the world, [so outsourcing production is] not cheaper, it is not faster, and since America is the best, it’s not better,” Marino stated.

Good for people who love T-shirts from their favorite small-scale creators. But kind of a problem for people who own creative works that are worth licensing.

Over the years, CafePress has found itself the subject of various legal threats and lawsuits, including one that significantly threatened its protections under the Digital Millennium Copyright Act. Parties as prominent as the GOP have threatened to sue them. And this problem has only grown more significant over time, as more sites have leaned on, and improved upon, the CafePress model.

Earlier this year, Wired highlighted the challenges facing many license owners who find themselves struggling to protect intellectual property on the digital frontier, with framing initial example used being The Texas Chainsaw Massacre, a film with enough of an interest that it’s frequently being targeted by ripoff artists.

“It was way bigger than we thought,” noted Pat Cassidy of the production and management company Exurbia in comments to the magazine. “These weren’t just 10 sites. There were a thousand of them.”

While companies like Redbubble and GearLaunch make a point of discouraging copyright-infringing uploads, there is still a significant problem, especially at scale, and while image-detection software can uncover some of it, it isn’t good enough for license holders in many senses.

Perhaps the closest they’ll get to a solution is by working out brand-licensing deals with the big sellers, like Redbubble, to give them some revenue access—which isn’t ideal and doesn’t cover every situation, but it’s also not an option Aerosmith had 40 years ago.

Then and now, bootleg T-shirts created massive headaches for those who owned profitable licenses. The difference is that now, at least, some of the players in this space are trying to be above board.

So, going back to Bart Simpson’s many mutations on T-shirts, a phenomenon that might be best compared to the clearly unlicensed (and Ford-defiling) Calvin & Hobbes decals that appeared on pickup trucks around the mid-’90s, the thing that’s most interesting in his case is that the bootleg parodies became an artistic medium in their own right.

Bart Tracy Bootleg Shirt

This particular Bart bootleg, found on Etsy, also adds in references to MC Hammer and Dick Tracy, two pop culture phenomena peaking around the same time as the shirts.

In many ways, many people saw themselves in Bart, and applied his demeanor and attitude to as many settings as possible—even if that meant making Bart a different race entirely.

As a 1990 article, originally from The New York Times, makes clear, one likely part of the reason for Bart’s evolution into a bootleg icon was a dearth of similar icons for Black Americans at the time, while also reflecting on how Bart’s general message—the cavalier attitude that upset the teachers of 1990—translates effectively.

“I believe there is a feeling in the Black community that Blacks are being blamed for a number of social ills that they are not necessarily responsible for,” the Washington, D.C.-based radio host Ernest White said in the article. “I guess this presence of the Black Bart T-shirt says there is an association with the underdog, a need to fight the establishment.”

It also helped that his design was fairly simple and easy to replicate—solid colors, solid lines, fairly recognizable shapes—which meant the bootleggers of the world could come up with something quickly to riff off a budding trend.

When I was researching this, I came across a video of Simpsons creator Matt Groening at an art gallery that was showing off examples of his creation mangled in numerous ways. Standing in front of a mashup of Bart Simpson made to look like the hot-rod character Rat Fink, he had this to say: “I would never think of any of this. I mean, I know what my drawing style looks like. I love people that are making it their own.”

And not only is he a fan of bootlegs on walls, he is apparently a collector of the bootleg items, according to a 2014 Vice article featuring “Leo,” the creator of the Bootleg Bart social media pages (which unfortunately only live on Twitter these days, after years on Instagram).

This is a bit of an evolution from his stance circa 1990, when these shirts were everywhere. “You have to have mixed feelings when you’re getting ripped off,” he said in a statement back then.

But over time, he appears to have come out on the other side.

When it comes down to it, so many of the complaints about counterfeiting are about money. Groening, while a creator who has obviously benefited greatly from the licensing rights afforded him by copyright ownership, clearly sees the other side of this equation as well. Maybe it’s a reflection of his roots in the world of alternative newspapers; maybe he finds the nature of creativity really additive.

But in a world where one can buy a T-shirt featuring an illustration of Mario wearing a sonic suit, I wonder if it’s a kind of acceptance that more of our creators need to take.

Find this one an interesting read? Share it with a pal! And thanks again to The Prepared for sponsoring us over the past few weeks.

Ernie Smith

Your time was just wasted by Ernie Smith

Ernie Smith is the editor of Tedium, and an active internet snarker. Between his many internet side projects, he finds time to hang out with his wife Cat, who's funnier than he is.

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