7. Embracing Being The Bad Guy - AXIS
It's one thing to realise that you have the potential to become a tyrannical rogue, yet it's something entirely different to thrive in the role of being the villain.
For Tony Stark, this is something that happened to him during - and after - the AXIS event of 2014. There, an inversion spell by Scarlet Witch and Doctor Doom caused our usual Marvel heroes to becomes villains, and our usual Marvel villains to become heroes. While AXIS concluded with the majority of these personalities being reverted back to 'normal', Iron Man underhandedly worked out a way to remain villainous.
This end result isn't merely Tony playing up his more arrogant, egotistical side, but instead Stark goes full 'bad guy' in the aftermath of AXIS.
Complete with shiny new white armour, the 'Superior' Iron Man essentially turns San Francisco into a city of drug addicts. Giving everyone the chance to experience his Extremis for free via a mobile app, not only do the San Fran citizens experience excruciating withdrawal symptoms when this wears off... but Tony charges them $99.99 per day to get their next Extremis fix.
Iron Man also purposely keeps it secret than the main 616 Earth will soon be under a full-scale attack from alternative worlds. In fact, the only way that the Armoured Avenger ends his villainous ways is thanks to the Marvel brand being rebooted with 2015's All-New, All-Different Marvel relaunch.