Well, Reed is unquestionably the closest to him. I mean, I know that fandom has this bizarre, mystifying belief that they don’t like each other, but that’s not at all what their friendship is like in canon. Far from it, in fact. They are very good, very close friends who care very deeply about each other and always have each other’s backs. I’d even say that the Starks and the Richardses in general are old friends and allies – Reed and Tony’s dads were close friends and partners for years while they worked for the Brotherhood of the Shield. (I don’t know if Reed and Tony met as kids, but it’s very possible if not likely that they did, given that their dads worked together.) And it’s a relationship their kids continued – Tony goes to Reed ALL THE TIME for help and advice when he needs it (which has been going on for decades), and Tony’s been there for Reed both as Iron Man and as Tony (pre-secret identity reveal). Personally, although I’m not a Tony expert, I think that Tony sees Reed as…goals. Not in terms of his intelligence or success or anything, just because Reed has managed to make a close, loving family for himself – a spouse, 15 kids, a brother-in-law, and a best friend who all adore and would never leave him – and I think Tony desperately wants that too, although he’s never quite been able to manage it for himself. They also both are very idealistic and forward-thinking and want the same things for humanity – to push them to be the best they can be. They’re kindred spirits in that sense. I truly get no sense of rivalry from them – they just genuinely love and admire and want to help each other, both in their personal lives and also their quest to make the world around them better.
They didn’t have very many on-panel interactions prior to the 1980s, but more contemporary writers have since retconned a friendship between Reed and Tony that dates back all the way to the early days of the Avengers and the FF, which makes sense if you think about it – they’re both scientists, and Reed at least has always had very close ties to the rest of the scientific community. Reed and Iron Man, however, interacted significantly less often and weren’t as close.
Reed and Iron Man first meet in Avengers v1 #3, where Tony asks Reed for help finding the Hulk, but Reed’s unfortunately in the middle of an experiment and can’t help:
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