I've been a fan of strategy games since I was a teenager, but the only game I find myself coming back to has been Tom Clancy's EndWar. Despite the relatively simple combat mechanics and lack of depth, that game made an impression on me because it was the very first strategy game I ever played where it felt like the units under my command were people and not unquestioning slaves.
Prior to EndWar, I played a lot of real-time and turn-based strategy games. While they no doubt had little bits and pieces of dialogue in gameplay, End War was the first one that did a good job at characterizing your units. Part of its success was in the fact that no two units of the same type sounded alike; the tank leader of team ANETO and team JUNGFRAU were distinctly different characters and had their own quotes.
These same units were also willing to question your judgement if you send them into hopeless engagements. Sending APCs to fight main battle tanks is suicidal, and they will let you know. They breathe with relief if you tell them to retreat after getting in a tough spot.
The ambient chatter was pretty good too; soldiers comment on seeing their allies getting wiped out. They give each other pep talks, and complain about the player's obsession with capturing uplinks. Units that survived multiple battles and got promoted also speak with more confidence.
The only other strategy game that comes to mind when it came to humanizing your units was Company of Heroes; the troops there would panic in the middle of firefights and would happily (or angrily) retreat when ordered to. The modern XCOM comes close, but there's something missing there. It might be due to the soldiers not conversing with each other in mid-battle, or making comments about things they find in the environment.
Share with me: Do you know of any other strategy games that do well when it comes to giving the units personality? Especially in mid-gameplay.