Absolutely correct...your turn.

Anyone recognize this li'l fella?

Such a big boy...can only be nicknamed Tiny.

Yes indeed! Somehow he's less unsettling than the original Tiny in -as you alluded to- Ninja Cop Saizou.

Your go.

Who knows this bad boy?

I'm guessing Von Horne, or Kolonel Weissekopf, or something...

He seems mildly annoyed by being spread with bullets. He has that "hmf, maybe I should say something about it or go sit elsewhere" look.

Grumpy fellow, I'd say.

JoeSapphire is onto something...

This character's name definitely has a German ring to it.

My best hint would probably be:
think of the name of a deceased guitarist of one of the "Big Four" of Thrash...and replace the female part with three other letters.

:)

Ohhh, that's great game

Recognized it as a boss from Kingpin:Life of Crime, but had to go and look up his name. Is it captain Heilman?

That is correct...it's your turn. :)

Cool, great game, at least initially. Loved the atmosphere, but the game started to feel very repetitive for me about halfway in unfortunately.

Here's the next one:

Cold chills race down my spine and a blast of adrenalin surges through my body as I realise he exactly matches the description of Jessie Bains.

Excellent :) I somehow managed to get past this part as a kid, even without understanding the first thing about poker :P
But yes, it's non other than the Death Angel, aka Jessie Bains.

Your turn.