That APA shirt is a masterpiece of bad design and I'm at least a quarter sure it was a rib on Bradshaw from someone.
Road Dogg's is such a lame biproduct of the time that I gotta smile a little. It at least was a catchphrase thing, I guess? Really do you wanna buy the Doggy Style shirt or the Suck It shirt to support the same people?
I can defend the arrow one on the grounds that 1.) arrow shirts were already somewhat of a thing and 2.) it was brought up on TV as a really dumb joke before it became a shirt.