I know plenty of Iron Man fans who have never read a comic before in their lives, as a comic fan, I try not to be smug about it. I give recommendations and usually get laughed at, but for those of you who haven't, read one! Give it a try. This recommendations list is found comic books subreddit's suggested reading. I can't agree with it more, so why bother creating a new one?
Invincible Iron Man Volume 1: The Five Nightmares
This compiles the first six issues of the most recent Iron Man (not counting Marvel NOW) and it a wonderful read. Obadiah Stone, the bad guy from the first movie, has a son named Ezekiel, and he wants revenge! Ezekiel is described as Tony Stark's equal and opposite, younger, faster, smarter. Besides all these things, he has the Iron Man tech!
Iron Man: Extremis
This book is actually had a re-release to go with the movie, as the movie takes some of its storyline from here. This book compiles the first six issues of the 2005 Iron Man series. A new technology is released and threatens all of man kind. While I haven't seen the movie, I highly recommend reading this before you go watch it.
Iron Man: Armor Wars
This is a little less modern, but still good. It collects Iron Man 225-232, and follows some deadly villains who get hold of the Iron Man technology and begin making their own. This is a very intense Iron Man story that is always remembered as one of the greats.
Iron Man: Demon in a Bottle
This is the classic Iron Man story. It collects Iron Man 120-128, this one is about Justin Hammer, from Iron Man 2, arranging an entire army of super-villains to take Iron Man down. Really should have been read years ago, but if you haven't, read it now!
Do I need to discuss the Iron Man live-action films? I'm not going to, I'm assuming the only reason people will be looking for more Iron Man is because they saw those films. Let's cover some lesser known ones.
The Invincible Iron Man
This was a direct to DVD movie in the same style as Planet Hulk. While probably the worst Marvel Animated movie, I think it does have some redeeming qualities. This film involves Tony Stark in China working on some kind of underground resource thing, a dragon attacks that is preventing the return of the Mandarin. Being as the Mandarin is the villain in the new movies, I would recommend giving this a watch before hand, but don't expect a whole lot. Watch it while it is still on Netflix!
Iron Man: Rise of the Technovore
This is the second Iron Man animated movie by Marvel Animation. While I haven't seen it yet, it is apparently like the Iron Man Anime in style and story telling. Norman Reedus of Boondock Saints and Walking Dead fame is voicing Tony Stark. Weird. Apparently it is about Ezekiel Stone developing a new bio-technology for Iron Man to take care of.
Iron Man has been showing up on the TV for decades, I'm just going to cover what I have personally enjoyed honestly...
To fit in with the popularity of X-Men and Spider-Man, Fox began airing numerous Marvel cartoons in the 1990s. One of these was Iron Man. The shows follows Iron Man and his friends, which are pretty much the West Coast Avengers. These include War Machine, Century, Scarlet Witch, Spider-Woman, and Hawkeye. The first season is pretty atrocious but the second reason really started to get great before it was cancelled. The show had a few crossovers with other shows like Spider-Man and the Hulk. Worth watching if you are a huge 1990s Marvel fan. Currently available on Netflix!
Avengers: Earth's Mightiest Heroes
Don't let the fact that this is a modern cartoon fool you, I've enjoyed this more than the Marvel Cinematic Universe so far. While not solely an Iron Man show, Iron Man is obviously a prominent character. The show is great for so many reasons, it might need it's own post. Just watch the first few episodes and tell me I'm wrong. Both seasons are currently on Netflix.
Iron Man Anime
I've never been an anime fan, I've tried so many times and never really found something I thoroughly enjoy. I did, however, like most of the Marvel Anime available. Iron Man is in Japan to build an arc reactor when the evil organization Zodiac intervenes he has to stop them. I sat down and watch this entire series from start to finish. It's not perfect, but certainly better than any other standalone Iron Man series. It was streaming for free on Crackle recently, but appears to be off of that now. I'm sure it will be back.
There really haven't been too many Iron Man video games, especially ones that don't suck. While he has made very notable appearances, he is rarely the main character. He is a playable character in X-Men Legends II, both Ultimate Alliance games, and has been playable in all Marvel VS Capcom games to date.
Marvel Nemesis: Rise of the Imperfects
This game kind of sucks, but Iron Man is a prominent character. The game is about some aliens that come crashing down to Earth, and begin infecting everyone. The game is a fighting game with level in between that involve fighting footsoldiers. It's not great, but there are not many Iron Man games, so I'm listing it.
Iron Man 2
Sega has released two Iron Man games that coincided with the release of the films. The first one was horrible, and the second one isn't much better, but still better. I really felt like Iron Man during this game. The game takes place after the events of Iron Man 2 and stars Iron Man and War Machine as playable characters. The game takes place in the air for the most part, and has a huge selection of weapons to choose from. It is far from perfect, but at this point it is the best Iron Man game we can get.