L7
True story: a friend of mine wore this to school on a casual clothes day (i.e., a day when we didn’t have to wear uniforms) and got sent home in disgrace.
Marilyn Manson
Shockingly, this didn’t go down especially well with Christian conservative types — in fact, back in 1998 one luckless teen was arrested for wearing it.
Bad Religion
Also unpopular with conservative types, although in fairness, it does look like the nuns are enjoying themselves.
Suede
Trolling before trolling was a thing, courtesy of 1990s England’s crown prince of debauchery, Mr. Brett Anderson. As of today, you can buy the damn thing on Etsy (although I would have already bought the shirt if it hadn’t been a women’s small).
Pearl Jam
Back before Pearl Jam were middle-aged lumpenrock mainstays, they were scatological 20-somethings!
Hole
A simple band name/song title combination, but presumably enough to cause conniptions in the parents of any girl trying to wear it out of the house. (Images from the My Band T-Shirt Tumblr, which is also an excellent read.)
Jane’s Addiction
Any of the band’s album covers would do, but still, there’s something singularly disconcerting about this particular image.
Melvins
You can’t quite read it because the image is blurry (it was the best one I could find), but the semi-naked female devil is saying, “Hey, what can I say? It’s a living.” Jesus looks less than impressed with her attitude.
Nirvana
Kurt’s views on fame and the music industry are crystal clear here. The irony, of course, is that there are about a gazillion places where you can buy this T-shirt today.
Arab Strap
And finally, this masterpiece, courtesy of gloriously squalid Scottish bedsit miserablists Arab Strap. We’d expect nothing less from the band who were responsible for this design (which, sadly, never did feature on a shirt).