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The pilot episode where Tom and Liz were greeted by several FBI agents outside their residence when they drove in from FBI Headquarters that the latter said that she didn't need to hitch a ride with her husband.
When Reddington was injected with a tracking device, he says "Ouch" in a bored tone like it's a normal routine for him.
Firmly cementing his status as a Magnificent Bastard: after forcing Harold to open the box, Red waits calmly until it has retracted all the way, adjusts his shirt and takes a step off the base of the cell before looking up and reacting in surprise, as if he had just noticed that he was surrounded by gunmen, hostages, and Anslo Garrick.
After dousing a money launderer in vodka, he sticks a lit cigar in his mouth... and then decides he's taking too long to catch fire.
Red: "Oh, the suspense is killing me!" (shoots the guy in the chest)
His interactions with Janice, Henry's (the banker's) wife, especially his exasperation at her constant screaming, eventually tossing her into the closet. Red even said sorry for ruining the dinner.
Red: "Janice, my sincerest apologies. I'll take a rain check on the stroganoff. It smells delicious."
This from "The Cyprus Agency":
Evil Cornered Lawyer: "The truth is, the agency is-" (immediately gets hit by a random bus)
Have you ever wanted to see Raymond Reddington act like a Camp Gay? "Madeline Pratt" grants your wish, where he does this to distract a guard and rescue a tied-up Liz, by among other things, claiming she's Bashir al-Assad's mistress.
Keen: What the hell was that?
Reddington: I don't know, it just felt right.
There's something inherently funny about Lance Reddick dressed as a cowboy.
Red sarcastically complimenting him on his hat, telling him it takes "a certain kind of man" to wear it.
The final exchange between the two, when Reddick's character says he's going to charge Reddington double for dealing with Jolene.
Red breaks into the Russian Ambassador's quarters and is found holding the man's adorable little dog in one arm and a knife in the opposite hand. When the Ambassador angrily warns Red that he will die if the little dog is hurt, Red pretends to be offended at the suggestion that he would hurt a dog, goes to give the little dog a kiss... and then tosses the knife straight into the Ambassador's leg.
Reddington's "negotiation" with Yaabari in "Lord Baltimore", which include air strikes on his camp in Cameroon. All without being nervous.
In "Monarch Douglas Bank", Red and Dembe go to visit a baker who also happens to be an arms dealer... and who dotes on Dembe like he's her favorite grandson.
Reddington's comments about Vargas in "Dr. James Covington". According to him, he resembles someone from a Humphrey Bogart movie.
Ressler telling Liz that he's Crazy-Prepared to have a spare key in case of emergencies. The said key being a crowbar.
Mr. Kaplan working on an impromptu autospy at the grave of a victim as if it was a daily routine for her. Liz kept her nose covered due to the stench.
Reddington trying to avoid getting Haskel mad over a Noodle Incident in "Dr. Linus Creel" that involves the latter waking up in a hotel room without any memory of how he got there.