As the Batman of the Marvel universe, it comes as no huge surprise that Iron Man is the man when it comes to outsmarting people. A potent mix of unreal tech skills, genuine tactical wit, and an ability to overprepare to every situation mean that Tony Stark is not only ready for any scenario, but he's also planned an intricate way to win it.
And while it's always interesting to see how he reacts when these plans fail, it's sometimes far more interesting to see what happens when they succeed, as his almost ludicrous plans - like mind wiping the whole planet, or rebooting a brain off of a floppy disk - channel all of the wonderful craziness of comics in the best possible way. Better yet, it generally doesn't feel out of character for Iron Man to carry any of this off, because - well, because he's Iron Man, so it's actually less weird the more elaborate his plans are.
With a not inconsiderable number of comics dedicated to showing Iron Man being dunked on by enough supervillains to start their own small colony, it's well worth exploring the times that Iron Man outsmarted everyone - to explain why he always looks so smug, if nothing else.