Whether it was Terrence Howard or Don Cheadle, Rhodey/War Machine has been onscreen as long as Tony Stark/Iron Man, beginning in the first Iron Man movie. As Terrence Howard said to the Iron Man silver suite, "Next time, baby."
Rhodey has been Tony's best friend since the beginning, but that doesn't mean he's always been at his best. War Machine has stepped out on his own a few times and that's caused a little bit of chaos and hard feelings. Below are a few of the times War Machine deserved better, and few times he was at his worst.
Felt Bad - When Tony Wouldn't Share the Humvee
When Tony goes to Afghanistan to make a weapons presentation in the first Iron Man film Rhodey, begrudgingly tells him he did a good job. Tony tells Rhodey that, "This is the fun-vee, the humdrum-vee is back there."
Of course, fans know how this turns out. Riding in different humvees Tony is injured, and captured, without Rhodey by his side. When reunited, eventually, Rhodey tells Tony, "Next time you ride with me, okay?" But Tony shouldn't have blown Rhodey off in the first place.
Hated - When He Was Angry Tony Wasn't Working With the Military
Again, in the first Iron Man movie, Rhodey is pleased that Tony seems to be healing, post-Afghanistan, but is less than receptive to Tony's implying his new project is personal, rather than for the government.
It's too bad Rhodey brushes Tony off because he could have jumped into the War Machine suit much faster if he hadn't. Still, at the moment, it's Tony the audience feels bad for, not War Machine. Tony was coming out of a rough place and Rhodey needed to be better at listening.
Felt Bad - When He Tried to Help the "Lone Gunslinger"
In Iron Man 2 Rhodey does a better job of being a friend when he sees that Tony doesn't look healthy. He tells Tony, "I'm looking at you. You wanna do this whole lone gunslinger act and it's unnecessary.
You don't have to do this alone." Tony, being Tony, blows him off. He explains that he knows exactly what he's doing. It's hard not to feel bad for Rhodey who, at the moment, is doing his best and it's Tony, this time, who's blowing people off and not listening.
Hated - When He Fought Tony on Tony's Birthday
Tony was not being his best self during his birthday party in Iron Man 2, even if he admitted that he didn't want to have the party in the first place. He's drunk, he's acting out, and Rhodey is trying to keep people safe when he initially puts on the silver Iron Man suit and tells party-goers to, "Get out."
However, things get out of hand as Tony and Rhodey beat on each other, and it's hard not to hate on Rhodey for not keeping his head a little bit more, since he's the one who, at the very least, is sober.
Felt Bad - When Tony Didn't Show Up at Caesar's Palace
At the beginning of the first Iron Man film both Rhodey and Tony are in Las Vegas and Tony is supposed to be accepting a big award. After the video tribute Rhodey calls Tony up to the stage, but Tony doesn't appear.
It's hard not to feel bad for Rhodey, being left in the lurch by the person who is supposed to be his best friend. Rhodey is doing everything the can for Tony and yet Tony can't be bothered to show up for Rhodey at all.
Hated - When He Spoke In Congress
If everyone, Tony included, had been patient and listened thoroughly, Rhodey would have been clear about how the positive aspects of Iron Man largely outweighed any of the negatives the government was worried about, of course, he never got that chance.
However, the fact that Rhodey didn't clearly and deliberately come to Tony's defense immediately is hard to swallow. It's hard to see Rhodey being loyal to his job over his best friend.
Felt Bad - When Vision Shot Him Out of the Sky
Not only was it horrible to watch War Machine get traumatically injured in a fight where it was good guys vs. good guys, it was made worse by the fact that Vision, who hit War Machine, was also on Tony's side (rather than Captain America's).
It was bad enough to see Avenger fighting Avenger, but when you're injured by someone who is fighting on the same side it's an even harder injury to swallow. Seeing War Machine unconscious in Iron Man's arms is heartbreaking.
Hated - When He Brought the Iron Man Suit to the Military
If the violent and dramatic fight at Tony's birthday party wasn't enough, after destroying Tony's house, Rhodey leaves, wearing the extra Iron Man suit. He doesn't just take the suit from Tony, he takes it straight to an air force base and drops it into military hands, which Tony, so far, had been avoiding.
It's hard to approve of any of Rhodey's decisions when it comes to taking stolen Stark tech to the government, and it's hard to see how Tony can later forgive him for it.
Felt Bad - When He Watched the Snap
Hard as it was to watch any of the Avengers observe the fallout of Thanos's snap, it may have been hardest to watch War Machine. Not only does he see his comrades disappearing in front of him, but he also knows his best friend is off-planet, and there's no way for him to know Tony's fate.
It's impossible not to feel bad for War Machine as the world becomes dust around him.
Hated - When He Worked with Hammer
If it wasn't bad enough that Rhodey took Stark tech to the military, it added major insult to injury when he allowed Justin Hammer to upgrade the suit.
It wasn't just that working with the military went against Tony's wishes, working with Hammer was a personal slap in the face to Tony's personal feelings about Hammer and everything he did.