Red-haired guy imagines himself as a beautiful woman with a portal gun going through an infinite portal loop.

Typical redditor.

A homestuck duck.

Unfunny and unwitty guy tells a "joke". Said guy is probably sheltered in and grew up with many privileges in life. Listener is not amused.

Ms. Pacman is smoking a cigarette.

Man fighting a dragon. He only has a sword, how futile.

A trilobyte, nautiloid, long fish, and round fish run from a giant sea predator with a pumpkin-esque face.

An enticing pie lying in the midst of three obvious traps: a 1000lb anvil suspended in the air, a flamethrower, and wall spikes. Well drawn

Fat guy cosplaying Spock.

Gish, the friendly black blob. Asks "L or R?"

Giant letters. It's a bit tough to make out. I think it's B E 4 T

A colorful fuzzy wuzzy.