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Iron Man:

• Tony at the beginning.

"I don't want to see this on your My Space Page. Please, no gang signs... No, throw it up, I'm kidding." "Yeah peace, I love peace! I'd be out of a job with peace..."

• • Also at the beginning:

Soldier: Is it true that you went twelve-for-twelve with the Maxim Girls last year? Tony Stark: That is an excellent question. Yes and no. March and I had a scheduling conflict but fortunately the Christmas cover was twins.

• Also also at the beginning:

Tony: I'm sorry, this is the fun-vee. The hum-drum-vee is over there.

• • And then after Tony is kidnapped and assumed dead, he is reunited with Rhodey, who finds him haggard, injured and near complete exhaustion:

Rhodey: How was the fun-vee? [Tony laughs]

• Pepper talking with the reporter who Tony slept with and subsequently dumped.

Christine: "Even after all this time, Tony still has you picking up the dry-cleaning." Pepper: "I do anything and everything Mr. Stark requires... including occasionally taking out the trash. Will that be all?"

• • Also this scene:

Pepper: I actually don't think that you could tie your shoes without me. Tony: I'd make it a week. Pepper: Oh really? What's your social security number? Tony: ... Five.

• "Okay, let's start things off nice and easy, see if 10 percent thrust capacity achieves lift. In three...two...one..." *WHAM!*
  • Then there's the bit just after that where he's designing the stabilizers.

"I did say I was done making weapons. This is a flight stabilizer. It's completely harmless." *Tony activates it and gets blasted back by the force* "I wasn't expecting that."

• Tony in the Mark II suit turning off the repulsors, then going through the roof, piano and one of his cars. Cue one of the workshop robots spraying him with fire extinguisher.
  • The previous scene:

Tony: If you douse me again and I'm not on fire, I'm donating you to a city college.

• The great unsung comedy moment of Iron Man, due entirely to Downey's brilliant deadpan delivery:

Party Girl: Hey, Tony, remember me? Tony: Sure don't.

• • The best part is that he doesn't even stop walking or turn to look at her as he says it.
• When Tony shows up at the party and he thinks he sees Hugh Hefner and pats him on the back, only for "Hef" to turn around and be Stan Lee.
• Tony's reaction to Pepper seeing him in the Iron Man armor;

"Let's face it, this is not the worst thing you've caught me doing."

• • Better yet, the dialogue between Tony and JARVIS while they're trying (off-screen) to remove the former's suit.

JARVIS: Well, it is a tight fit, sir... Tony: Ow! JARVIS: Sir, the more you struggle, the more this is going to hurt. Tony: Be gentle, this is my first time.

• Two words: "Icing problem?"
• A brief moment during the final fight scene. Tony's just started getting out of his suit, thinking that he's won and he can take it off, when Iron Monger appears behind him. He turns and lifts his hand to deliver a repulsor blast... Only to find that he's already taken the armored glove off of it and his hand is bare. He actually turns his palm to stare incredulously at it for a second before getting slammed in the face.
• "TONY STARK WAS ABLE TO BUILD THIS IN A CAVE! WITH A BOX OF SCRAPS!" "Well I'm sorry... but I'm not Tony Stark."
• The little exchange between Coulson and Pepper while they infiltrate Sector 16.

Pepper: Oh what is that, some kind of device to pick the lock? Coulson: You might want to step back... *blows the lock*

Iron Man 2:

• Tony hacking into the senate committee's computers from his PDA over wi-fi and having it display "WELCOME MR. STARK" in ASCII art. Followed immediately with footage from other people's failed attempts to create Iron Man suits..

Tony: Boy, I'm good...

• • In fact, the entire scene was hilarious from Tony's "Yes, dear?" to Senator Stern's launching of a Precision F-Strike at Tony on a live international broadcast.
• The senate hearing is equal parts funny and awesome, but the best part had to be Justin Hammer frantically trying to block the TV as it's showing Hammer Industries' Epic Fail at trying to reproduce the Iron Man suit. Especially when the top half of the suit twists 180 degrees around. Crosses the Line Twice at its best.
  • Made even better by the fact that there were originally just blurry satellite photos to try and prove that other countries had Iron Man level tech, so Tony remotely hacked into the system with his cell phone and patched in video surveillance from these failures, including Hammer's.
  • Made... umm... even more better (?) considering that said scene is {a possible} remake of a scene from RoboCop 2. One would think they would have learned by now.
• JARVIS is wonderful at providing these moments. For example, in Iron Man 2, when looking at a YouTube video of Tony's senate meeting. "May I say how refreshing it is to finally see you on a video with your clothing on, sir."
• Stark and Pepper running into Hammer in Monaco, who has the reporter from the first movie with him.

Justin Hammer: She's actually doing a big spread on me for Vanity Magazine. I thought I'd throw her a bone, you know. Pepper Potts: She did quite a a spread on Tony last year. Tony Stark: And she wrote a story as well! Pepper Potts: It was very impressive, very well done...

• A nice little Mood Whiplash after...Whiplash has been causing chaos at an F1 race. Happy Hogan rams Whiplash with a car, then does it repeatedly every time he tries to move. Made even funnier by the fact that Pepper is screaming at Tony and Tony is just saying "Hand me the briefcase" repeatedly while showing virtually no reaction.

(after Happy Hogan runs into Whiplash) Tony Stark: Who were you trying to hit, me or him? Happy Hogan: I was trying to scare him- Tony Stark: Cause I can't tell!

• The first scene between Justin Hammer and Ivan Vanko (in the airplane hangar) has this gem. This is a conversation where Vanko so far has said and done nothing besides sit there and look at Hammer blankly.

Hammer: You and me, we're a lot alike in a lot of ways. Vanko: *Fascinating Eyebrow*

• One standout scene was SHIELD agent Coulson finding something that looks a lot like Captain America's shield amongst the clutter of Tony's laboratory. Tony asks Coulson to hand it to him, since it's exactly what he needs to deal with his current problem... and shoves it underneath his equipment to make it level.
  • This is even funnier after Coulson's Captain America fanboy status is revealed in The Avengers Movie.
  • Coulson gets another one earlier; he is assigned to keep Tony from leaving his house. Tony acts like himself, and Coulson just grins and threatens to tase our hero, and then watch Super Nanny while Tony drools into the carpet.
• Hammer's ridiculously hyped Ex-Wife missile's magnificent un-success.

Tony: Hammer tech? Rhodey: * disgusted look* Yeah.

• It's more like a Crowning Moment of Snigger, but This Troper was highly amused by Tony's spontaneous christening of the Hammer drones as "Hammeroids".
  • Not the first time we've heard that name...
• Tony "entertaining" the guests at his birthday party, completely shitfaced (bottle in hand), all while wearing his Iron Man suit definitely deserves mention.

"A lot of people ask me how I go to the bathroom in my suit." (pause– smile) "....just like that.

• • Even funnier is when Pepper calls him out on pissing his pants, he mentions there's a filtration system in the suit and adds "You could drink that water!"

"The party's over... well, it's been over for me an hour and a half ago. BUT THE AFTER-PARTY STARTS IN 15 MINUTES!!!"

• Later:

"Put on a phat beat for me to beat my buddy's ass to."

• • He put on Another One Bites the Dust.
• Tony and Pepper having an intimate moment after the day is saved, only to be disturbed by Rhodes, who had been watching them the entire time.
  • "You look like two seals fighting over a grape" has to be one of the highlights of the movie.
  • "Get a roof" may be a Shout-Out to The Count Of Monte Cristo's (1934) "Find your own tree."?
  • Just the total deadpan delivery between a couple of guys in metal battle suits arguing like five year olds.

Rhodes: You look like two seals fighting over a grape. Tony: Hey, you weren't supposed to see any of that. Get lost. Rhodes: I was here first. Get a roof. Tony: How much did you ... Rhodes: All of it. I've been here a while.

• Tony having Fury appoint Senator Sterns to present his award for defeating Whiplash. Sterns is clearly not happy about it. Said senator actually gets one himself in the process when he 'accidentally' pokes Stark with the medal pin.

"(to Rhodey) You deserve this. ... (to Tony) And you deserve this. *jabs him* Sorry. It's funny how annoying a little prick can be."

• Many of Fury's lines in the second film are downright hilarious. One example is when Tony is sitting in a giant donut prop and Fury finds him.

Fury: Sir! I'm gonna have to ask you to exit the donut! (Tony pulls on his shades slightly as a silent Flat What)

• • The donut in general. Tony lounging around in full armor except for the mask in a donut shop's giant donut, pigging out because he's slowly dying. In character but utterly ridiculous. Fridge Logic reveals a Offscreen Moment of Awesome: he must have walked into the donut shop in his armor to buy those. Like the Uncomfortable Elevator Moment in Spider-Man 2, but even more so.
• Another example when the two are discussing the fate of the Mk 2:

Tony: I didn't give it to him, he took it. Fury: Whoawhoawhoa- he took it? You're Iron Man and he just TOOK IT?! The lil' brother walked in there, kick'd ass and took. Your suit.

• And pretty much the entire exchange while Tony is reading his evaluation to Fury, the latter not saying a word as Stark tries to justify his many flaws.

Tony: "'Mr. Stark displays compulsive behavior.' In my own defense, that was a week ago. 'Prone to self-destructive tendencies.' I was dying, I mean please. And hey, aren't we all? 'Textbook...narcissism? (Looks up at Fury.) Fury: (Glares back) Tony: (Looks back down at folder) Agreed...

• • There's something strangely hilarious about a man wearing millions of dollars of hi-tech weaponry, the head of the world's top espionage agency, and a professional shadow/spy lounging around a doughnut booth like it's no big thing.
• No love for Howard Stark? "I'm Howard Stark... and on behalf of everybody at Stark Industries, I would like to show you... my ass."
  • Also a sorta twisted Crowning Moment of Heartwarming Like Father, Like Son moment. You can definitely see where Tony gets it from.
• Tony's line when he inserts the arc reactor with its new core into his chest, curing his palladium poisoning and granting him previously unimaginable amounts of power:

Tony: Whoo! Tastes like coconut! And METAL!

• We also have this line:

Vanko: I make salute.

• Also:

"One down!"

• Black Widow casually macing a Hammer guard as she walks past him. Moments later, Happy, who finally managed to drop the one Hammer guard at the front, turns to yell in triumph, only to see an entire hallway littered with unconscious guards that Romanov casually beat her way through.
• Tony has some good ones as well. Being chased by War Machine and a swarm of Hammeroids:

Tony: JARVIS, break in! I need to own him!

• One of Hammer's goons threatens to kill Vanko's bird and stuffs it in a bag. When the film cuts back to the scene, the man is dead and the bird is perched on him. Honestly, Vanko's burd is one of the best parts of the film.
• Happy biting the guard's ear. HE BIT HIS EAR!
  • It's dirty boxing, and it's been around forever.

Iron Man Anime:

• Nanami and Tony are made of funny.
  • The initial Crash Into Hello.
  • Tony immediately hitting on her, and her Armor-Piercing Slap response.
• Dr. Tanaka's reaction to the air show.

Tanaka: So much for humility.