I have one from a band called Massie that says “you work hard, I’ll be sexy”.
Makes me laugh every time.
I also have a t-shirt with a purple teddy bear under a paragraph of text telling a nihilist horror story in broken english about that teddy bear as if he were a real person.
Both winners.
I don’t have a lot of T-Shirts anymore, but my favourite is probably one from a youth club in eastern Germany with Boss “MyName” (but the wrong spelling) on the back, and the logo of my late father’s long bankrupt company as a sponsor on the front.
It’s funny, but more in a nostalgic way.
Very cool, thanks