The haircut looks familiar - Er Ist Wieder Da?

Correct. AKA Look Who's Back for US audiences.

Half scripted comedy, Half Borat style man-on-the-street improv. Check out the Trailer Here

Haven't even seen it yet.
But have read the eponymous novel the film was (fairly faithful from what I've heard) adapted from.

Next one:

Reminds me of Ralph Bakshi...

Edit: But I can't remember any films of his with this scene in it. Also, the lines are too clean and the shapes are well-made :P sooo, probably not a Bakshi film.

Gonna guess - The Haunted World of El Superbeasto?

Damn, already had a couple more lewd stills lined up.

You're it.

Here's a new one, sorry about the quality, best I can make with the file of the film I have:

Maybe post another hint?

I will post a new image tomorrow morning (UK), but for now a hint::

"Phillabusters".

I'm not sure, but is it the movie where Brad Pitt says he can speak a little Italian, so as not to blow his cover, and then proceeds to say "Arrivederci." in a very American accent? I don't wanna play next, so I won't name the Tarantino film in case it's that one :P

Before Brad Pitts time

Heres two new images.

Don't know this film, but there seems to be something going on about contemporary things inserted into a historical setting. Maybe a spoof of that type of error? Or a mix between two time references.

is Ed Harris in this film?

Yes.