In preparation for Infinity War (sort of), I just re-watched Iron Man (2008) for the first time in 3 years. Some thoughts:

• I guess they were doing this on purpose, but early Tony’s attitude toward women is really pretty gross… and Pepper kind of reinforces it with her loyalty to Tony and her attitude toward the women he sleeps with (“sometimes I even take out the trash”). That seems to support the stereotypical division between women you hook up with and women you marry – trashy, disposable women and respectable, valuable women. That aspect of the movie has not aged well.
• I also kind of winced at the generic Arab-looking terrorists. Yinsen did say they were from a variety of nations, speaking a variety of languages including European ones, but they still all looked vaguely brown and threatening. As usual, that part of the world is mostly divided into villains and victims; Tony needs to fly in with his high-tech suit to save the poor villagers (though it was a good touch that he didn’t personally take vengeance on the man who captured and tortured him). Yinsen is something of an exception, since he’s shown having skill, ingenuity, and initiative… but then he sacrifices himself to save Tony. Of course.
• Having gotten used to Don Cheadle playing Rhodey, it’s very weird to see Terrence Howard in the role. What a strange recast. Facial structure, skin tone, vocal register, and general manner are all completely different. Don Cheadle strikes me as more serious, so more believable as a high-ranking military officer, but Terrence Howard seems more like the kind of guy who hung out with Tony Stark in college and continues to put up with his shit.
• I love Coulson so much. It’s so funny to see him in his first movie appearance, now that he’s become a running gag and then a sacrificial lamb and then one of the heroes of Agents of S.H.I.E.L.D. He does mild-mannered and put-upon so adorably.
• How far Tony Stark has come! And Robert Downey, Jr. has shepherded him gradually and organically through his maturation from self-centered, immature playboy to cocky, self-assured part-time hero to struggling PTSD sufferer to adult man trying to carry the world on his shoulders (and co-raise a teenage kid) while still maintaining a dry sense of humor and a cool facade. Tony has had the most consistent, compelling character arc in the MCU and surely one of the major reasons for that is that RDJ cares so much about him and goes to bat for the integrity of the character.