When presented the challenge of grabbing a flag on a very high flagpole (the reward is a jeep ride back to base with Carter), something no soldier has managed in over 17 years. The other soldiers scramble all over each other trying to scale the pole, but (pre-supersoldier) Rogers outsmarts his stronger squadmates by simply detaching the pole's anchor bolts and letting it fall over, rather than trying to scale it. The soldiers' and drill instructor's faces when he pulls it off are priceless.
Gotta love the part when some kids in the audience notice the Hitler impersonator sneaking onto the stage, and say things like, "There he is, Cap! Look Behind You!"
When Cap has rescued the prisoners and tells them to clear out while he searches for Bucky, we get this exchange:
Soldier: Wait. You know what you're doing? Steve Rogers: Yeah. I've knocked out Adolf Hitler over 200 times.
Before the procedure starts, we have everyone in the lab stopping dead in their trackswhen they see Steve for the first time. Peggy's reaction is just a resigned sigh and a "let's just get this over with" expression.
However, after the procedure she's Not So Stoic. She's as gobsmacked as everyone else, and actually sneaks a feel of the dazed and newly transformed Rogers, before pulling back.
When one of the news films shows that Steve has a picture of Peggy inside his compass, Phillips give her an amused half-smile.
Phillips' "He's making me cry" line regarding Steve really cracks me up. It has everything to do with Tommy Lee Jones' delivery and expression, which is completely deadpan as usual.
In a Deleted Scene, Philips scolds Steve for blowing off his award ceremony which resulted in Senator Brandt being humiliated— then cracks a smile and says that he deserves a medal just for that.
Just about every word that comes out of Colonel Phillips' mouth, but his interrogation of Arnim Zola takes the cake... Or is that steak?
(Zola nervously studies his cell... is that blood beneath that operating table...?) Phillips: Sit down. (Phillips puts down a tray of food at a table.) Zola: What is this? Phillips: Steak. Zola: What is in it? Phillips: Cow. (Dr. Zola stares at it dubiously.) Phillips: Doctor, do you realize how hard it is to get a-hold of a prime cut like that out here? Zola: I don't eat meat. Phillips: Why not? Zola: ...It disagrees with me. Phillips: What about cyanide? Does that give you the "rummmbly tummy," too?
And then Phillips promptly starts eating the steak himself.
Zola: You’re trying to intimidate me, Colonel. Phillips: I brought you dinner?
On a related note, Phillips' later description of Zola as "my new best friend" when he's debriefing the others.
Philips giving a speech to the new recruits, and as he says "We are going to win this war because we have the best men", he suddenly pauses and stumbles over the last word when he lays eyes on Rogers, a foot shorter than the other troops and still skinny and scrawny. He then ab-libs "And because they are gonna get better... much better..."
Steve reuniting with BFF Bucky Barnes, who notes his friend's transformation.
Also kinda counts as a moment of awesome for the kid.
Stan Lee's cameo during the award ceremony upon seeing a backstage aide tell the senator Rogers isn't there and mistaking the aide for Rogers.
Lee: I thought he'd be taller.
When Senator Brandt starts demanding answers for how a HYDRA agent got into the testing area, Colonel Phillips counters by saying "Great, why don't we start with how a German spy got a ride to my secret installation in your car."
Red Skull's first meet with Cap: "Captain America! How exciting! I'm a great fan of your film!" in an obvious mockery tone.
When the Skull and Zola are fleeing from their exploding lab, Zola points out that the Skull's escape Triebfluegel only seats one. The Skull responds by calmly turning to Zola and handing him the keys to his car.
It's the fact that you think that the Skull is going to just leave Zola behind, but then...
Followed by the sight of Zola looking pretty gleeful as he drives away in the HydraMobile.
When Schmidt is being chewed out by the SS officers, he makes a hysterical 'One Two Three' motion with his fingers, pointing at the Nazis, just so he can adjust his death ray properly. All without pausing in his speech.
And when one of them starts to yell at him and declares he will be punished by Hitler for his treachery, Schmidt raises his eyebrows and makes a head motion to the effect of "oh really?" Then when he begins firing, one of them dodges a couple shots and he scowls, like he's thinking "Oh come on!". Finally, when he connects with the next shot, he gives a little nod, as if thinking "There that's better."
On a similar note, as Schmidt is preparing his death ray, there's a technician sitting behind the SS officers who immediately and casually walk out of the way.