#2 The Rock: Poontang Pie
As I said in my previous list of the Best Shirts in Pro-Wrestling history, the "Austin 3:16" shirt was extremely influential. It inspired other wrestlers to print shirts with catchphrases on the front and logos on the back (or vice versa).
Enter The Rock, a man with many catchphrases. Among them were "layeth the smacketh down", "if you smell what The Rock is cooking", "The Rock says...," etc. He also had another one, but surely he wouldn't make a t-shirt out of that, right?
He did. He absolutely did.
There was a time when The Rock gained an affinity for eating "pie". But Rocky wasn't referring to grandmother's signature homemade apple pies - he was referring to women's genitals. He loved this type of pie so much that he made it into a t-shirt. The shirt featured a blue Brahma Bull eating a pie with no utensils and the words "Poontang Pie" in all caps underneath it.
Uhmmm... (Yeah, take a moment there my friend!)
First of all, that's a really dumb looking bull. Look at his face - he's got nothing going on upstairs. If a non-fan were to see this, what would go through their mind? Why would anyone allow their children to wear this? Why would anyone let themselves wear this? This is like the Val Venis shirt from earlier, only worse because The Rock was the much bigger star.
This shirt represents just about everything terrible about the Attitude Era - puerile humour, forced sexual humor, and rampant misogyny. I can only think of one worse...