Iron Man vs. Batman Begins

It is my personal opinion that Iron Man is cooler than Batman. I don't declare myself a Marvel comic fan, nor do I argue that Marvel is better than DC(...well maybe I do). Actually I own no comics. With a gap between their original comic book appearances that is over twenty years long, I don't think the two were ever really meant as "rivals". The Punsiher might come in there somewhere. I'll let Lee and Kane take that one on. In fact I intend to use only the movies IronMan (2008) and Batman Begins (2005) to make my arguement rather than the comics or previous Batman films (and let's face it, it is a favor to Batman that I don't take the "nipple armor" into account here).

1. Sidekicks
Morgan Freeman and Michael Caine are clearly cooler than Gwyneth Paltrow and Terrence Howard as the assistants/accomplices. Dr. Yinsen is a great character also, and I'll give him his credit later, but he's not really a sidekick. I'd call him a catalyst almost. Sgt. Gordon is a sort of a sidekick, but he's often out of the loop and doesn't really contribute much except as a lieison between vigilante and police. While Gwyneth's Pepper Potts is a pretty coolheaded woman, I lean more towards Alfred as the assistant and I'll count her more as a love interest than a sidekick. Alfred, played by Caine in this movie, raised Bruce and is the quiet guide behind the brooding bat. Morgan Freeman (a personal favorite of mine) is just awesome as Lucious Fox and the character itself is well done. Howard's Rhodes doesn't really have a big role in this movie (although let's hope he gets some of his comic book airtime in the next movie) so I can't really count him properly. In this case, I will give Batman the cooler sidekicks between these two movies.
Point goes to Batman.

2. Love interests
This one is a hard choice. Gwyneth Paltrow and Katie Holmes are both hot in different ways. So I can't judge this one on hotness alone (again I am not taking Maggie replacing Katie in to consideration here. Lucky for Batman).
Both Pepper Potts and Rachel Dawes are independent women who tell the hero how she feels leaving no assumptions (again, not taking Maggie's Rachel in to account). They know our heros well and even get into the action and help them succeed.
But I'm giving Pepper the win here. She loves Tony Stark for who he is and accepts that he IS Iron Man. She cares about him and everything he is, including his need to be a kickass vigilante, his general playboyness and his wit. Rachel loves Bruce Wayne but tries to change him and make him choose between being Batman and being with her. Given Bruce's coneceit is just an act, I think Rachel should accept him as both Bruce and Batman. It's part of him.
Point goes to Iron Man.

3. Gadgets
Batman and Iron Man both have kickass baubles for crime fighting. They both have awesome suits (and houses and cars but those don't count unless they use them in crime fighting). I admit this is another tricky choice. Iron Man's total suit or Batman's Batmobile and Batsuit? Flying at Mach 3 or sweet ninja moves?
Both have amazing abilities not given to them by a laboratory experiment gone awry but instead by engineering and sheer guts. Iron Man can shoot fire, fly, deflect bullets and lift cars. While Batman can glide with his cape and come and go like a ghost, nothing beats shooting fire from your hands in my book. However Batman doesn't need anything but body armor and his mad skill to defeat the low-level badguys.
So I think it comes down to this: Tony Stark invented all of his gadgets and Bruce Wayne buys his from Lucious Fox.
The fact that Tony invents his suit and is an all around genius gives him the win here. By a LOT.
Point goes to Iron Man.

4. Nemesis/Mentor
Ra's al Ghul/Henri Ducard or Obadiah Stane? The man who trained Bruce in his ass-kicking ways or the man who acts as a father figure and business partner? Both hero/villain pairs end up with almost the same capabilities in the end, Henri having trained Bruce and Obadiah having stolen Tony's invention. It comes down to a battle royale that our heros both win by allowing their foes to fall in upon themselves without being the ones to physically kill them.
Jeff Bridges plays Obadiah. He is just freaking evil. He wants money and power and he doesn't care who gets hurt (not even US Military or Tony himself). He's mean and ugly and has no qualms about having blood on his hands. He betrays Tony and steals his technology intent on ruling the world with his own giant evil-armor and we learn he orchestrated Tony's kidnapping.
Liam Neeson plays Ra's al Ghul. He firmly believes than Gotham is corrupt (and who can argue?) and must be destroyed for the greater good. Scarecrow is kind of a secondary guy here. It's really Ra who is behind it all he's just using Scarecrow and Falcone for his own ends. He's smart and uses evil people to do what he thinks is the best thing for Gotham.
Despite how generally evil and greedy Obadiah is, I always say that the best villians are the ones who think they are doing what is right (like Khan or Vader). In this case, that is Henri.
Point goes to Batman.

5. Origin
Both movies tell us the origin of Bruce Wayne's and Tony Stark's vigilante alteregos.
Tony is in the Middle East visiting US Military and demonstrating his latest uber weapon, the Jericho Missile. He's being his usual witty and alcoholic self when he is kidnapped by insurgents using other Stark weapons. He's nearly killed by shrapnel from the ambush and one of his fellow prisoners, Dr. Yinsen, saves him. Tony then invents the device that will keep the metal out of heart and eventually power the Iron Man armor. The terrorists want him to build his uber weapon for them, and geniuses that they are, give Tony all the tools he needs to build a GIANT MISSILE LAUNCHER while in captivity. Instead he builds the prototype Iron Man armor and escapes, blasting them all to hell with Yinsen's help. (Did they really think anything other than that would happen? Idiots.)
When Tony gets home, he's a changed man. He's still witty and a bit self involved but he's seen the other side of war. He wants to help people and get his weapons out of the wrong hands. He then builds a better suit and device to power it. And so begins Iron Man.
Batman is a little different. His start in this movie is not as straightforward and actually a little confusing to me. The entire movie is his beginning so it is more involved. He too is a rich boy who inherits a multinational, multibillion dollar industry from his parents. We see their deaths in flashbacks. The movie begins with him somehow kidnapped in Asia, he is rescued by Henri and trained in the ways of The League of Shadows. He wants to avenge his parents' murder and thinks the best way to do this is become a criminal himself. He only turns to the "good guys" when he realizes the League won't just let him avenge a murder, but wants to destroy a whole city. Bruce gets the Batsuit from Wayne Enterprises (who I think makes body armor and armored cars and such) and helps the police bring down a complex web of crime headed by the League. He then agrees to help them in the future and they install the Bat signal. And so begins Batman.
Both movies have their touching moments and show you where the "flip moment" came about.
I gotta say I enjoyed Tony's start more than Bruce's. So many moments in Bruce's story make you cringe and think he's just going about this the wrong way and might be making things worse for himself. He doesn't even get to avenge his parents properly: the other bad guys assassinate Joe Chill before Bruce can get to him. His turning point is a little more gradual. Tony used his ingenuity and skill to escape. He did lose Yinsen in the fight, who really shows him the good in people that is worth saving. Yinsen's death is really Tony's moment. He then uses the rest of the movie to fix the actions he regrets rather than seemily creating more.
Point goes to Iron Man.

6. Character/Personality
Two millionare playboy alcoholics with totally different personalities. Bruce mostly pretends to be a womanizer to hide his alterego and drinks because he is so conflicted. Tony IS a womanizer for the most part and drinks in a party-boy fashion. Tony is way more fun loving and cool than Bruce is most of the time. Bruce just can't seem to keep it together and tries to spearate himself and Batman. He can't. They are one (no matter how he might try to change his voice, that little lisp gives it away. Sorry Bruce). Tony openly admits that he is Iron Man.
The suit is Tony's engineering and the computers he uses to create it are his own inventions. The fact that the armor is completely his brainchild makes it all the more connected to him. Bruce buys the Batsuit as more of a disguise and protection.
Both heros have close friends who know the truth but Tony is less conflicted than Bruce about leading a double life. Bruce's whole life seems dark whille Tony uses his humor to lighten the darker moments. Bruce is tortured inside (all the time) deeper in his turmoil and pain and he turns to the good side mostly on his own. But I have to give the win to Tony. While his pain isn't as deep (we see a little bit into it at the press conference) his reform is really amazing. Yinsen's death and self sacrifice truly change him and his world view even more than the kidnapping does. He goes to such lengths to do the right thing and doesn't seek out personal gain or revenge with his power. Plus he just depresses me less.
Point goes to Iron Man.

So I give Iron Man the win overall win with a score of four. Batman is cool, I admit it. He has more movies, a longer run and maybe even more fans. And he definitly takes the trophy for Least Words in an Awesome Theme Song ("Na-na, na-na, na-na, na-na, Batman!"). But Iron Man just kicks ass and takes names with that suit, that genius, that heart, and that humor (and Black Sabbath's song "Iron Man"? It isn't really about the comic book hero if you listen to it, but I admit I have that guitar riff as a ringtone). You don't have to agree with me. My own sister is on the Batman side of this rift. But in the end, I just really dig Iron Man.