some dude giving another dude some news, not really sure if its good or bad (he could be suicidal)

It's a blue Converse shoe. Kinda ugly because blue isn't a good colour for that type of show, so yeah. Draw it.

It's a confused, but happy stick person.

A trippy ass whale or fish. Can't tell what it is, really. *Damn, look at those eyes.*

It's a cannon shooting out a used tampon. Not much else to say.

Two people sitting in jail, presumably men because they are bald, but it could be bald women, too. They are sad.

Draw the thing you fear most.

It looks like a guy from the mafia... Doing god knows what. Good lord, what am I looking at? What was this supposed to be?

Captain Crunch is upset and ready to fight about something.

This person has a mess of black pubes, they are growing rather wildly.

Sonic, better than the real Sonic. (Because he's an over-confident, outgoing douche)