Who else but Quagmire?
quagmire
brown haired man/girl (possibly an orangutan?) waves at you
A black man waving good bye.
Sad shadow
Some character I don't recognize but vaguely looks like if Sonic the Hedgehog retired at age 55 and became a judge.
An aged Sonic the Hedgehog regrets spending his rings on a Law degree.
Doodle or Die is the game of "telephone" with drawing!