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We Met the World's Leading Authority on Bootleg Bart Simpson T-Shirts

A UK man is creating an online archive with all the best unauthorized Bart shirts. His collection includes Bart smoking weed, Bart hanging out with LL Cool J, and Bart fighting in the Gulf War.

The Simpsons is a cultural institution, a television series that can cause grown adults to lose all sense of sanity when they find out a character on the show might die—a cartoon character, no less. But back in the early 1990s, it was still fresh, still earning its place in the cultural lexicon. That first wave of popularity was marked by an intense public fascination with a rude, insolent, snarky, skateboarding boy named Bart.


Bart Simpson merchandise flew off shelves faster than stores could stock it, and intense demand created the black market entrepreneurs who sold what have come to be known as "Bootleg Bart" shirts. Bootleg Bart shirts put Bart and other Simpsons characters into numerous bizarre and varied situations. Shirt designs could have Bart playing for the Chicago Bulls, single-handedly defeating the Iraqi army, or smoking copious amounts of marijuana, or being suffocated by an obese woman's rear end. If you grew up watching The Simpsons in its early seasons, chances are you owned at least one of these illicit pieces of clothing. You also probably gave most of them away or they fell apart from the ravages of time and overuse.

Fortunately for classic Simpsons fans, a mysterious UK man who only goes by the name "Leo" is collecting Bootleg Bart shirts and maintaining a home for these outlandish images across numerous social media platforms. His goal is to preserve as many Bootleg Bart shirts as he possibly can, while also educating people on the numerous ethnic and racial issues that come from making Bart Simpson black. I spoke to him in the middle of yet another round of Simpsons mania.

VICE: What got you started collecting Bart shirts, and when did you decide to create your online presence?
Leo: I was seven in 1990, and like most kids around the world, I loved The Simpsons. In addition to Bart shirts, I had bootleg Roger Rabbit [clothes] that my mom used to bring back from the market. I always found them funny, with the colors all mixed up. I remember going to Western International Market and seeing the Bart Marley shirts.


In 2003 I got myself a couple of Bootleg Bart shirts for a laugh. Whenever friends or family went on holiday and asked if I wanted anything, I would always say "a Bootleg Bart shirt." I was introduced to social sites and thought it would be cool to start up my own little page sharing my shirts and other bootleg Simpsons images that I had found. I wanted to make a place online where people could go and reminisce, have a laugh, and remember a time when The Simpsons was brand new. I have to give a shout out to a Flickr group that inspired me called "Growing Up Star Wars." You should check it out.

How many Bootleg Bart shirts do you own?
A lot of the shirts on the Instagram feed are from the followers of Bootleg Bart. It's a community site where people make contributions. My collection keeps changing because I sell some, but last time I checked it was around 60. It will grow, and the dream is to do a touring exhibit, with an "educational museum" feel to it.

You've got a book coming out. What can we expect from that?
I've been working on a book for years and have teamed up with someone this year to make it happen. I wish I had more to say on it. For updates visit

Have you spoken to anyone at 20th Century Fox or the Simpsons production office about what you're doing?
Me personally, no. I have no idea how I would get in touch. I would love to, though. How good would it be to get their blessing? I know Matt Groening collects bootlegs. I remember him showing some of his collection in a documentary years back.


Did Fox ever try to halt the sale of Bootleg Bart shirts? It seems like there were so many different versions out there that it would have been impossible to stop it all.
Yes, Fox did successfully seize sellers back then. It was mainly the counterfeits—the shirts that were trying to pass as official merchandise. They also destroyed a bunch of shirts that had Bart posing as a Nazi.

A lot of the Bootleg Bart shirts made Bart black, and he was used as a symbol for resistance to apartheid, for rasta culture, and hip-hop music. Was this just a coincidence of history, or is there something about Bart Simpson as a character that encouraged that?
When I was seven, I didn't know what race meant. I didn't think once why the Simpsons where yellow. But yeah, Bart was funky as hell. For starters, he had a high-top fade and two hit records, one by Michael Jackson, one by Jazzy Jeff ("Do the Bartman" and "Deep Deep Trouble"). So yeah, back then he was fresh to death.

Sometimes, when I show older people photos of Bootleg Bart shirts, they get offended, particularly any Black Bart shirts. There's one in particular where Bart is a rasta and has big red lips similar to racist caricatures of the past.
Oh, for sure. There are some really offensive Bart shirts. I think the worst one I've seen is a Gulf War–related one with Bart shoving a gun down some guys neck saying, "How much is the price of oil now, raghead?" I think that's why it's important for the book and exhibit to happen—so it can paint the political landscape at the time and put things into context.


If someone saw a Black Bart shirt out of context, it could look real racist. But if you know the subject matter, then you understand it. But yeah, there are some real fucked-up ones. I get private messages all the time telling me how much of an asshole I am for posting some of the shirts.

Speaking of the Gulf War, Bart was depicted as a giant, muscled soldier with a gun a lot, which is a bit weird considering the character is a child. 
Yeah, Bart was used on all sorts of Gulf War propaganda. If The Simpsons wasn't ahit show at the time, I'm sure it would have been some other cartoon character. Maybe the Ninja Turtles?

The show has been around long enough that it's had the opportunity to be a pop culture fad more than once. When the show first premiered, Bart was arguably the most popular character, but it seems like that's Homer now. Why was Bart so initially appealing, but less so in the present?
Yeah, you're right. I love the fact that The Simpsons has grown up as I have. A lot of people bash the show now for not being like how it used to be, but the couch gags alone smash anything I've seen on TV. You don't need to watch the full episode if you don't want to, but man… watch those couch gags.

I don't know a lot about [Homer's popularity] really. I guess it might have something to do with the writing. Bart is kind of annoying these days.

Do you have a favorite Bootleg Bart shirt?
Man, I can't chose one. I've got one of Bart, Nelson Mandela, and a map of Africa backdrop with Bart saying, "The dude's my hero." Love that one. I'm a big fan of the Hawaiian shirts, with the Simpsons as luminous green geckos. And last but not least, a Bel Biv Devoe, LL Cool J, Betty Boop crossover with Bart staring at Betty Boop's ass.

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