How about movies with voice-overs? "Trainspotting," "High Fidelity" & "Annie Hall" come to mind.

I've thought about it and decided on - please no drum rolls -

The Riffs of Dennis Farina

He's one of my favorite "cool lines characters" and has totally had some of the best lines ever.

Or - what is it with the drum rolls -

The Coolest Robert Loggia Lines
yet another one of those go to guys for not-so-stock characters. I'm searching for the trailers but I'm sure everyone has seen them.

I have to go with Dennis Farina. Just his lines from Snatch are golden.

Crap I forgot the movies:

Snatch
Get Shorty
Little Big League
What Happens in Vegas
You Kill Me
Striking Distance
Reindeer Games