This is Robert Downy Jr Iron-Man vs Anthology Batman, as in the one from Batman, Batman Returns, Batman Forever, and Batman and Robin.
So here is the set up...
After the events of Iron-Man. Stark begins to her rumors about masked vigilante in Gotham running around killing people at the same time Wayne Enterprises. Begins to make some aggressive moves toward Stark Industries assets in Gotham. So in attempt to put away Batman and stop Wayne Enteprises. Stark moves his operation to Gotham, gets a mansion on a hill over looking the bay and nearby corperate headquarters. Assume he has more or less the same set up he did back home. His mission is two fold as Iron-Man take out Batman and as Stark stop Wayne. Of course Wayne knows he is gunning for him on both accounts.
For this scenario.
Tony(Iron-Man) will have the his 3 completed suits from the film as well as the Iron-Monger suit all in working order. He has his company/employees(including Potts)/security personel. As well as limited support from the military/SHIELD. Which includes Rhodes as a liason. Just to clarify Stark can loan out his armor if he wants.
Bruce(Batman) will have every suit and gadget he had in all 4 films(Batman, Batman Returns, Batman Forever, and Batman and Robin) as well as every vehicle. Both planes, all three batmobiles, the boats etc. As Bruce he has all his regular buisness assets. As Batman he has help from Robin and BatGirl. They are also fully stocked on vehicles, suits, and gadgets. Of course he also has Alfred. He also has limited Police/Local Government support.
So when these 2 playboy, billionare, superheros go head to head both on the street and in the office. Who comes out on top?
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The Batwing is packing missles and machine guns. We know that a high volume of fire from either can "dent" Iron-man's suit. So can significant physical impact. Such as getting punched about by Iron-Monger or getting hit by a car. So a combined air ground assault with the Batmobiles and Batwings is an option.
How agile/fast is the Batwing compared to the jets IM faced?
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Speed is hard to tell, but it's(they) proable not as manouverable. They may not even be as durable.
In some ways staying grounded and using the armerment on the Batmobiles might be a better option for Batman and as Iron-Man hunting Batman it shouldn't be hard for Batman to pull Iron-Man into a confrantation. In an enviroment that negates many of Iron-man advantages.
On the other hand Batman may actually be able to effect Iron-Man's suit in straight melee combat. He after all punched threw the floor plating/armor of the Batmobile. From an awkward sitting position in "Returns" and headbutted threw aircraft glass in "Forever". His hitting power combined with his reaction time(blocking bullets that is) may allow him to rattle Stark inside the armor or even "dent" the armor himself.
After all Iron-Monger was struggling against weakend IM in terms of strength. Iron-Man at this point was lifting with serious effort 3-4 tons(the SUV) and Iron-Monger was able to damage his armor, with appearently similiar strength. Bending steel requires 3,600psi or almost 2 ton of pressure. Mind you this is for low grade steel. So it stands as a low end estimate for Batman's striking power power, but it should put him in the ball park to hurt Iron-Man if he hit him(Stark) right.
What about Batmans cape? remember when Batman made it go solid and it saved him from the flames?
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Nolans Batman would be better than Anthology Bats and he doesn't have half as much toys. But he's way better at stealth. He could break into Stark's apartment, kidnap Rhodey and Potts ect.
But Anthology Batman...........his best thing is his Batwings from '89 and '95. Iron Man spars with F-44 Raptors.
Keaton's Batwing is a complete joke compared to the two F-22 Raptors Tony both took a pounding from and out manuered/out flew. In Batman Returns, the Joker took out the Batwing with a single bullet, from a long barreled revolver. Does the Batwing even have guns?
So in the air, the IM suit obliterates anything Batman has.
On the ground, it's hard to tell, but Tony's gear seemed far more advanced and his armaments definitely looked deadlier. His repulsor beams and mini-missile might very well take out the Batmobile, hard to judge the Keaton-Batmobile. How was it destroyed again? The other Batmobiles were jokes.
Only clear advantage I see Wayne having is in a h2h fight, no suits/gear, he beats Stark into a pulp (and then rapes him anally, if it's the homosexual Cloony-Bat version.)
Nolan Bat's is no better at stealth then Anthology Bats. Remember Anthology Batman could pull the appear and disappear thing to. Just look at the fight in the chemical plant. The difference is most of the time Anthology Batman chose not to. He really didn't need to as much. Given bullet timing reflexes, class 2 strength, and a bullet proof suit.
[bwing]Which Tony can likely take, at least the guns. Even then, he's far more manuerable, most likely faster and the Batwing would go down from one minor hit of his.
[bmobile] I only recall the Keaton one dropping those mine-like bombs to blow up the factory, those certainly won't hit Iron Man. The machineguns, won't be an issue either. Only thing is it's durability and if it could withstand Tony jumping/flying on it and ripping off the hatch. How was it destroyed again?
He wouldnt be able to repell that armour piercing shit that he hit that tank with. Wayne might even explode inside his suit if he gets tagged with that....which'd be something to see....
As long as Iron Man takes Robin out too, its all good.