Finally, after years of browsing i managed to find some crying scenes with Gary Cole, from this show.
I only saw him crying in Fatal Visions and i was dying to see him crying in Midnight Caller since i saw the first series when i was little and i could vaguely remember some parts. There's not much crying from him but the few scenes are very deep felt , very empathetic crying. I had the impression that this one was hard to catch as a crier. He didn't played very emotional guys but i was pleasantly surprised.

This one is with him breaking down in the hospital hall after his former girlfriend announces him she has Aids..( it starts at around 19:00 ). The way he's voice breaks is amazing even if we don't see much tears.

http://www.dailymotion.com/video/xqmf5f_midnight-caller-sezonul-1-episodul-3-after-it-happened_shortfilms


( it Starts at 17:50 )He recollects the time when he killed his partner by mistake and he had to tell his wife what he's done

http://www.dailymotion.com/video/xqmdgf_midnight-caller-sezonul-1-episodul-13-ethan-s-call_shortfilms

( from 19:24 on and the ending)
 http://www.dailymotion.com/video/xqmc9b_midnight-caller-sezonul-2-episodul-7-someone-to-love_shortfilms