On a second viewing with Belle, Iron Man is a much more ambivalent film than it seemed the first time around. It's a movie about a superhero who does very little in the way of superheroics except defend his corporate interests. It's about an industrial magnate who wants to give up building weapons, but still for some reason has missile systems loaded into his post-conversion set of armor. And at heart, its main character is a guy who is capable of doing good not because of training or ideology, but because he was born rich and was once forced to confront his own unwitting privilege through a loss of control.
Many of these issues are inherent to the source material: any decent movie based on the Iron Man character, coming from a comic book as he does, is going to have to work around the shift in the medium. Successful adaptations--and Iron Man is very successful--have done so by minimizing the silliness of the genre, often keeping the main character out of costume as much as possible (the Spiderman movies use much the same strategy, as does the new Hulk, apparently). That said, the weakest part of the film is certainly at the end, when Obediah Stane goes on an armored rampage for no other possible reason than to fuel the movie's closing confrontation. After all, Stane is otherwise shown to be a shrewd manipulator and businessman, who's already working to move Tony Stark out of his position through channels both legal and illegal. There's no particular reason he should be bothering with a waldo-powered fistfight, except that it makes for exciting comic-book cinema.
Still, never mind all that. Because for a large chunk of its running time, Iron Man purports to be both self-contained and realistic-ish, meaning it doesn't matter that I know nothing about the comics and the characters that they set up. I don't need to know that Tony Stark, in the Marvel universe, is a long-time alcoholic, nor the complicated twists and turns of his business empire. I can happily ignore those in favor of the movie itself.
And what that movie presents, speaking glibly, is Batman without the ninja correspondence courses.
Tony Stark becomes Iron Man because he's held prisoner by a set of Afghani militants, and forced to recognize that his weapons are not being used to defend freedom and the American way, but also to arm guerrillas and terrorists. That's why he thinks he becomes Iron Man, but it doesn't address how he is able to do so, except indirectly. Because of course, Stark's ability to fight crime is based entirely on his wealth, his education, and his connections. He's an entitlement superhero. He has infrastructure.
This actually makes Iron Man a little old-fashioned, which is why a post-Cold War film adaptation is so interesting. As Matt Jones points out, Iron Man has a great deal in common with the classic Bond villains, who flaunted their wealth and power through elaborately-decorated lairs (or as Christopher Frayling is quoted in Jones' post, "machines for being a megalomaniac in.") The comparison with Batman, therefore, is actually flawed: when Bruce Wayne was traumatized, he responded by refining himself and acquiring new abilities separate from (although still funded by) his family's advantages. Tony Stark, in contrast, retreats back into the coccoon of Stark Enterprises. Batman is dangerous even when disarmed. Tony Stark, barring incompetent villains who provide him with raw materials, is not.
I don't think this makes Stark more or less sympathetic, although that's hard to gauge given Robert Downey Jr.'s charismatic performance. But it is illustrative of exactly how much the character is founded in privilege, and how much he still needs to grow. Indeed, you could make some very interesting social commentary with this as a starting point. In his 2007 book White Like Me, anti-racism activist Tim Wise comments on the rash of school shootings by white students at places like Columbine. He notes that those shootings by white students, which are characterized by their pointless, nihilistic goals, may in fact be spurred by the fact that white Americans are cushioned by their privilege. They are told by society that they are meant to be powerful and in control, and when they are placed in situations where that is not the case, they often lack the coping mechanisms to deal with them effectively. Privilege allows those mechanisms to atrophy, and the result is mania: school shootings, white collar crime, and other destructive behaviors far more common in white Americans than in the minority population.
As an explanations of Stark's transformations go, I think that's pretty good. His journey is roughly equivalent: a massive psychological shock delivered by the realization that he is not, in fact, an invincible force for good. And I think it's intriguing to consider the film in that frame. Because it's clear that while he's become more cognizant of the consequences of his actions, Tony Stark by no means understands how his new behavior is, in its own way, just as destructive as his previous arms dealership. He's trying to solve those old problems by using the same technocratic tools to reinforce his perception of self-superiority. The only change is the form factor--and the exaggeration of the privilege that caused his trauma in the first place, by placing Stark (instead of a trained military bureaucracy) directly in command of those dangerous technologies.
Of course, if Stark ever realized that, he'd have to conclude that the best thing he could do as Iron Man is take off the armor for good. And there's not a lot of Marvel marketing money in that scenario, no matter how psychologically or socially satisfying it might be.