A dude with crap on his head says "OW!".

A very ugly baby.

A sign saying "Red" above a piece of crap.

Sniper is Australia, oh, he's also a dentist.

Sniper realizing he's drunk.

Spy sitting on a duck with an unamused expression.

An adorable (and well drawn) pocket medic.

Demoman is pleased to have found an ungodly amount of gold.

It's coffee... And it's hot... IDK, draw one of the mercs drinking it or something.

A spider tries to give Medic hot chocolate. Medic beckons for Archimedes to help him be rid of the adorable arachnid.

Ballad of the Hats.

Someone refuses to drawn something, so they instead drew a butt. One shudders to imagine what horrors they could possibly be referring to.