Tarnish notte the majesty of my TOWER of HATS.

A man has too many hats

one who wears a lot of hats, jack of all trades, classy

A dog wearing a hat

sad dog in a cap

Sad ass as a kid

pink face with tear tattoos

crying pink guy

A man when he realizes that his life has been entirely wasted in bars, chasing tail. Also, he's grinning because he got some sex out of it.

demoman tells his dark secret

The devil speaks unspeakable evil

satan swearing?..O.o

now you can pay to avoid hell

high priest wants his money.