Funny t-shirts are a strange thing. You could ask 10 different people what makes a funny t-shirt funny, and you'll get 17 different answers. That's just the way humor works.
For me, a funny t-shirt has to have that "WAIT, what did his shirt say?!" element. That little (or big) something that when the random wearer walks into a public place as you're walking out, the shirt catches your attention, makes you smile, makes you laugh out loud, or even makes you want to stop him and say "excuse me, I need to read your shirt, do you mind?" (I've actually had complete strangers say that to me, and it's kind of funny, in a strange way). So when I create a design for a funny tee, I always keep the "WAIT!" element in mind.
Here are some of my personal favorites from PopTeez:
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