- Matt Bomer as Anthony “Tony” Stark/Iron Man
- David Henrie as 16 Year Old Anthony Stark
- Jon Hamm as Howard Stark
- Jaime Ray Newman as Virginia “Pepper” Potts
- Columbus Short as James Rhodes/War Machine
- Yun Dawei as Ho Yinsen
- Karl Urban as Boris Bullski/Titanium Man
- Elias Koetas as Edwin Jarvis
- Paul Bettany as J.A.R.V.I.S
- Owaine Yeoman as Happy Hogan
- Kevin Spacey as Obidiah Stane
At a masquerade, Howard and his wife Maria are dancing when Howard is tapped he turns around and a man reveals himself to be Boris Bullski. Boris asks Howard if he is willing to team up as he has a business proposal, Howard tells Boris to leave as he is trying to have a nice time with his fiancée.
A now aged Howard is walking in his lab when he asks Maria where Anthony is, Tony is then seen test driving a Armoured Truck for the US Military. Tony walks up to the General of the Base who introduces him to 19 year old James Rhodes a new Soldier. Tony is called by his father who tells him to come home quickly, Tony arrives at his house where he is told that his parents went on a Business trip and will miss his 17th birthday. Tony is then told that his parents hired a Bodyguard, the bodyguard introduces himself as Harold Hogan but he tells Tony he can call him Happy to which Tony replies “You don't look very Happy”. On Tony's birthday he is asked to step out of the party by Happy, Happy tells Tony that his parents plane crashed in the mountains and that they were cleared deceased. A heartbroken Tony steps into a office the next day where he meets Obidiah Stane who asks him if he is ready to take over his fathers company.
9 years go by and Tony is demonstrating a weapon which he calls the Icarus Missile which based of the Greek Legend of Daedalus and his son Icarus does what Icarus did, the missile when high enough blows up into smaller rockets which using their heatseeking abilities take out their enemies. Tony signs a contract with the Commander of the Base so that they can use his missiles, On the way back the cars in front and behind blow up after being shot with RPGs. The soldier driving Tony begins to drive faster to the base but they are rammed by a Armoured Truck. The soldiers manage to get Tony out the jeep and begin heavily shooting the truck which sends out a group of men with assault rifles to finish off the remaining soldiers but fail.
Tony takes cover behind a large rock when one of his missiles land a few yards away from him, Tony begins to run but is still blown back and a shard of the missile lands in his chest. Tony is taken by some of the terrorist into a van but falls unconscious during the drive, Tony awakens on a table and finds his chest open and a man operating inside of him.