"I should buy a boat" and "blackjack and hookers" image macros usually require external context to be understood. So you can't even tell if they're funny or not.
I at least chuckled at the "I'm not racist, I'm just a hipster". That said, I'm not a hipster so it doesn't personally insult me and I don't see how the image is at all relevant to the text.
The other generated images are just dumb.