Before 2008, Iron Man comic books weren't all that popular, or at least Iron Man was not a stand out. Well, after RDJ got his hands on him that changed in a big way. There are a ton of great Iron Man storylines, some of which have been realized on the big screen, like Extremis and Iron Monger, but some of the best Iron Man story arcs can only be found in the books.
If you find yourself Iron Man-curious, but don't know where to jump in, you're not alone. It can be very overwhelming to try to figure out where to begin with 50+ years of history, and who wants to start at the very beginning? That's a lot of work.
Fortunately for you, what follows is a list of the 20 best Iron Man stories, a number of which are good starting points, as Tony, like all characters has had no shortage of reboots.
The Confession is one of the best storylines within Civil War. A repentant Tony laments the actions he took in his pursuit of Superhero Registration that resulted in the death of his friend Steve Rogers. There is even a little redemption for Tony in this, whose actions throughout Civil War were sometimes questionable. Written by comic book superstar Brian Michael Bendis, The Confession is a must read.
If you've seen Iron Man 3 you're familiar with Extremis (though, the purveyors of it are conflated in the movie). Extremis is a nanotechnology that enhances a subjects physicality and gives Tony Stark the added ability to mentally control his suit. Artist Adi Granov is largely responsible for creating the visual look adapted by the film franchise, and writer Warren Ellis gets credit for injecting new life into an old character in this not-quite-reboot, that inspired Tony's cinematic origin story. It's basically one of the freshest Iron Man stories out there, and it's relatively short, so check it out.
Demon in a Bottle is, not surprisingly, a tale of Tony's struggle with alcoholism. When this was written by David Michelinie and Bob Layton in the '70s, it was absolutely groundbreaking for taking on such a monumental issue in the panels of a comic book. Today, it remains quintessential to the character, and much of the storyline was adapted to Iron Man 2, including the introduction of Justin Hammer. It is a seminal work in Tony Stark's canon.
World's Most Wanted is perhaps the best of Matt Fraction and Salvador Larroca's work. It pits two uncommon enemies against one another, Tony Stark and Norman Osborn, who replaces Tony as the director of S.H.I.E.L.D. and makes Tony a wanted (iron) man. Tony is forced to flee abroad, always pursued as he tries to destroy all of his work so Osborn can't get his hands on it. In the final battle he must don the original Mk I armor to defeat his foe. It's a cool throwback with some beautiful art.