On to the next round.

My first gut reaction was Capitalism, but I know that's the wrong game. OpenTTD seems to fit the bill.

It does indeed fit the bill.

Over to you.

Someone please take my turn. Don't have the time right now to draw anything.

So call me hardcore in paint drawing... Sorry for not many things on it but don't have many time to draw.

Edit:Ok i can't draw...

Looks like no one else has taken the turn, so here's a picture that may be impossible.
I did try to make the characters' faces sort of resemble themselves, but... yeah.. :p

/edit: here's a hint picture. proportions be damned, I'm not sure if the game actually has palm trees but it just feels like there should be, and the sniper is supposed to be a woman but I can't draw women :p
/edit2: here's another sniping picture, this time without Scope since that seems to be what the cool kids do nowadays. all this sniping might make you feel like it's a Hitman game :p

Hm, my first thought was Jagged Alliance, most likely 2 or "Back in Action" (although I haven't played that one) because:
- the architecture, the fence and palm trees are typical for any JA game
- almost all characters wear tank-tops there
- Ivan always has such a stereotypical Russian hat on his portrait like your dude
- the one guy on the first pic reminds me of "Scully"
- the one guy on the second pic reminded me of one of the avatars you can choose for your alter ego
- the sniper reminded me of Scope (despite the fact that he's not female)

Edit: Oh yeah, also the sniper has a cup of tea and Scope is British.

Sheila "Scope" Sterling is a guy? I'm pretty sure she's a woman, the game refers to her as a "she", I think, and there's the whole Sheila thing :p
Anyway, Jagged Alliance 2 is correct.

/edit: didn't mean to sound like a smarty-pants, she's probably my favorite mercenary in the game and for a moment I got all confused that maybe I remembered such a basic thing incorrectly

I've redeemed the game, cheers muchly, I used to have Master of Magic on a retail disk but someone walked off with it so I feel a little more complete again now!

I meant that in your version it's a guy while it should be a woman obviously (you even commented on that yourself :B). She's one of my favourite mercs too.

Anyway, next one (very easy).

Ahahaha!! Assassin's Creed

EDIT I'll post the next one now. IF ASSASSIN'S CREED IS WRONG EVERBODY IGNORE THIS
(Perhaps no-one's heard of it so it's one of those "literal" ones as well. should be breakable.)

This the most confusing rebus I've ever seen o_0

This one is suspiciously easy.
Bugs Bunny: Lost in Time
(haven't ever played or seen it, btw. but I've heard the title pretty often)

And yes, Assassin's Creed was obviously correct.

So who was the last one supposed to be? I recognised Ivan and Scully, the tea next to second one suggest Sidney Nettleson, but I have no idea about the last one.

The sniper was a male version of Scope (who is also British), not Sidney (he said that the sniper is supposed to be a woman but he can't draw women :P). And I'm quite sure that the last one is one of the possible faces for your alter ego.

Also: Next picture.