Robert Downey Jr
Ewan McGregor
Jeremy Renner
Colin Farrell
Colin Firth
Aaron Paul
People I want to see cry include:
-James Roday, particularly as Shawn Spencer from Psych. He sort of cried in the series finale, but didn't quite make it to full tears, and I always want to see the sassy smartass ones fully break down.
-Peter Capaldi, particularly as the Twelfth Doctor. I looked very closely and I don't think he ever shed a single visible tear his entire three-series run. Not even when River Song looks at him and specifically says he is crying. I had an interesting time with Twelve and I really wanted to see him cry. Nine, Ten, and Eleven all cried, and it was heartbreaking.
-Clark Gregg, particularly as Phil Coulson on Agents of Shield and various MCU movies. I'm almost to the end of the final season and I don't think he's going to fully cry and I really wanted to see that. He's one of my absolute top favorite MCU characters. He almost cried a couple times, and he once sorta cried from a combination of pain and distress, but again, never quite full tears or audible definite crying.
-Honorable mention to Max Riemelt as Wolfgang in Sense8. I spent like the whole show wanting to see him cry, and in the very last episode he had a truly fantastic crying scene. Sometimes you get exactly what you want, and more than you thought you could ask.