I don't know if you were around or aware enough of pop culture in the early 90s to remember Sinead O'Connor. She was a very popular singer. She was a beautiful young lady from Ireland with a voice of such range and ability that she could shatter frozen hearts. She had her big break in North America with a song (that she didn't write nor had any emotional attachment to) called 'Nothing Compares 2 U'. It was a good song and she sung it very well, but she made a decision some unknown time before filming the video that has cemented her in the public consciousness – she shaved her head.
Much of the video was a close-up shot of her singing into the camera, and so her near-baldness couldn't be ignored. This had two effects – on the one hand, the song had the potential to sling-shot her into superstardom, but the look was immediately latched on to and she became an object of derision, scorn, and mockery.
Then she brought her politics into things. She refused to perform on Saturday Night Live because Andrew Dice Clay was hosting. She refused to attend the Grammy awards in spite of the fact that she was nominated in four categories because she said they were a corrupt organization. She made some statements that were interpreted as supporting Saddam Hussein. Finally, the piece-de-resistance, on a performance on Saturday Night Live (sans Mr. Clay) she tore up a picture of Pope John Paul II, declaring him to be the enemy. The backlash was hard enough that her North American career was finished.
These political actions are remembered clearly by music fans and pop culture historians. There's some controversy about her intentions and mental stability. Did she deliberately attempt to destroy her career? Maybe. I happen to agree with her on several points. I wouldn't set foot on the same stage as Andrew Dice Clay, that misogynist prick. I think the Catholic church has been responsible for a great deal of harm around the globe in between cultural colonization, institutional racism, rape-enabling, not to mention the crusades and the inquisitions, and Pope John Paul II in particular, living in the age of AIDS as he does, promoted the idea that it would be better to spread the disease like a plague than it would be to use condoms and so put a stop to the possibility of a child being conceived.
But what do we remember most about Sinead O'Connor? That she shaved her head. We still make jokes about it to this day. Whenever we see a bald lady or even a bald man, we make a Sinead O'Connor joke. We could easily make a Brittney Spears joke, but I think we accept that she shaved her head as part of kind of a breakdown whereas we clearly thought and continue to think that O'Connor shaved her head with a sound mind.
Why does this stick in our collective craw? I don't really know, but I do think the staying power of the image is reflective of our discomfort with women acting outside their expected behaviours. Have you seen a picture of her lately? My partner bought one of her newer CDs back in 2003 and she let her hair grow back in. Time passes, you know. She's moved on but we still make jokes. But it was so jarring to our early 90s sensibilities that we just can't let it go. I guess it's a good example of how 'well-behaved women rarely make history' if only it were for something more notable. I guess her level of femininity wasn't good enough for us then and continues to fail to live up to our standards.