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    Season 1 
  • 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.
    • When Harold Cooper shows up:
      Red: Evidently, someone with the authority to make decisions has arrived.
  • Anslo Garrick, in a brief cross into Laughably Evil:
    Tom: Who the hell is this?
  • 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.
    Red: Anslo, what are you doing here?
  • A few of the moments from Red's Roaring Rampage of Revenge manage to come across as this:
    • 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: "('Laughing) Oh, my God, 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."
    Red (after locking a freaked out Janice in the closet): Janice, if you don't stop your yammering I'm gonna have to shoot through this door, which will be a shame because I won't have any idea what I'm shooting at..
  • Red casually swinging on a swingset in "General Ludd."
  • 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.
    Reddington: Why?
    Cowboy: Because I don't like you. And that hat makes your head look stupid.
    Reddington: Finally, the pot meets the kettle.
  • The unusual sight of Dembe eating ice cream while surrounded by a huge stash of weed.
    • In a previous episode, Dembe randomly complimenting the color of Lizzie's kitchen.
  • This gem:
    "Dembe, get the hacksaw; we're gonna have to take this guy outta here in pieces."
  • When Red, Dembe and Liz are holding an agent of Berlin captive and are about to move him, the agent seizes an oppurtunity and kills himself by jumping out of a seventh floor window. Red, Dembe and Liz are shocked for a moment. Then Red says "okay, then" in the most casual tone imaginable and starts leaving anyway.
  • While Red is talking to an associate as the latter swims in his pool, Red has this gem:
    Reddington: I was a lifeguard my junior year in high school. Had to give CPR to Mrs. Beerman...she coughed up a lungful of corn beef and chlorine and I haven't been in a pool since.
  • 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.
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    Season 2 
  • 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. note 
    • 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 autopsy 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.
  • Every scene with Glen Carter.
  • In the "The Mombasa Cartel", Samara talks about how parts of exotic animals were used to cure a number of diseases. When she says erectile dysfunction, she glances meaningfully at Aram.
  • Luther Braxton and Red discussing philosophical quotes.
    Red: A wise man can learn more from a foolish question than a fool can learn from a wise answer.
    Braxton: Is that Nietzsche?
    Red: No, Bruce Lee.
  • Samar teases Aram near the end of "Deer Hunter" by telling him that he's still sexy even if he goes bald. Aram denies it at all.
  • Crosses into Black Comedy when Reddington shoots Earl in "T. Earl King VI" with a revolver his two sons were using for Russian roulette since it previously failed to fire.
    Red: (After shooting Earl) Oh, my God. What are the odds?
    • Earlier in the same episode, Elizabeth gets a call from Tom, who ends up giving her some pointers about going undercover, like pretending to sneeze if someone asks a question that might trip her up.
    Liz: I always thought you just had allergies.
  • When Liz was interrogated by a judge on the cases Reddington worked on in "The Major".
    Judge: How many of these cases has Reddington given you?
    [Montage of cases Liz and the Task Force has worked on]
    Liz: He keeps us busy.

    Season 3 

  • Aram hugging Ressler at the end of "Arioch Cain". Ressler warns him not to do it again over a misunderstanding when ADA Reven Wright thought that they were having a Ho Yay moment.
  • Reddington's blackmailing of a Venezuelan official in Virginia by giving him a hug and telling him that the photos could seal his fate if the press knows of his meeting with Reddington. He later says that it's for his photo album.
  • Liz greets everyone in the Post Office for saying their regards to her. She tells Aram she liked his trashy novel gifts.
    • Baz tells Liz he likes her short hair after telling her that Red moved her neighbor Zoe to a nicer apartment.
  • Reddington promised Glen two blonde willing women if he would find someone as fast as possible. Reddington presents Glen with two Pomeranian dogs he took from the previous Blacklister.
  • In "The Vehm" as Red confronts one of his contacts in his hiding spot he demands two things: The name of the villain of the week, and a song. As they start singing (with Red conducting with a BBQ fork) the look of utter disbelief of Dembe's face is hilarious
  • Tom chastises her for risking her life to bring Reddington his gun bag. Liz says she can't guarantee she'll do the same thing again.
  • Ressler is in disbelief that he saw Aram smoke a cigarette. Aram insists he did it just to break some thoughts from Liz's funeral.
    • That's not a cigarette he's smoking...after all, as Navabi points out, it's legal in DC.
  • During a heist on Kirk's Super PACS, Solomon busts out what is possibly the best one liner in bank heist history.
    Solomon: Everyone stay calm. We're your friendly neighborhood bankrobbers; except we're not from the neighborhood, and we sure as hell ain't friendly.

    Season 4 
  • Double with the funny in "Miles McGrath" when Reddington shoots his courier when the former tells him to screw himself. This made him very very afraid of the man.
    Reddington: [After shooting Miles' courier] "You were saying?"
  • In "The Lindquist Concern", when Ressler and Navabi informed a lawyer that someone stole his identity, the latter mentioned that he's black. The lawyer frowns and says that his ethnicity is not a crime.
  • After a bunch of FBI agents capture a suspect in a school in "Adrian Shaw":
    Boy: You’re not supposed to have guns in school.
  • Reddington kills a ruthless slave worker and diamond smuggler in his own apartment in "The Forecaster". Right on time, the "cleaners" the man uses show up, non-plussed to find their boss in a pool of blood.
    Woman: You did done him?
    Reddington: I did done...do it.
    • Red introduces Dembe with the male cleaner remarking "aren't you a tall glass of chocolate milk." Dembe's face is priceless.
      • The female cleaner explains the two are "moonlighting" from their real job...cleaning up police crime scenes.
  • "The Harem" has Margot mentioning something really funny when she confronts a criminal in his nightclub.
    Margot: This one says she reads people. Like those, uh, FBI mindhunters who predict behavior. That's nonsense, right? But I will be damned if she didn't just predict yours.

    Season 5 
  • In "Smokey Putnam", Red shoots the ceiling of the house where Putnam is hiding to scare him into coming downstairs. Only for him to fall through the ceiling. Liz looks over and seems about to burst out laughing. Red's reaction is priceless.
    Red: Now there's an entrance.
  • In "Ilyas Surkov", Tom complains to the baby when he contemplates on solving the mystery on the bones missing from Kaplan's luggage.
  • Red turns out to have no idea what Star Wars is about.
  • Red goes to a genius hacker...who's a 15 year old Japanese kid living in his mom's basement. And then his mom finds him with Red and throws a fit. Red had tried to bribe her with four spiders as a gift...unaware that in Japanese culture, four is a homonym for death.
    • The gang are alerted to goons entering.
    Red: We'll leave through the hole in the fence.
    Mother: There's no hole in fence. (she sees her son grimace and gasps) I sit.
    Liz: They'll kill you if they do.
    Mother: Good, end the misery.
    • The woman spends the rest of the episode just glaring at Red silently, which completely freaks him out.
  • Raymond has to "admire the testicular fortitude of a man using the alias Wee Willie Winkie."
  • Red goes to help a friend out with a drug dealer.
    Red: There's something quite on the nose about a drug operation inside a candy factory. I can't get Sammy Davis Jr. out of my head."
  • Brimley the unusual Torture Technician makes his return.
    Brimley: I need some pastrami.
    • And when he says there's no useful information to get out his latest subject:
    Red: Are you sure?
    Brimley: Does an opossum have 13 nipples?
    Red: ...I honestly have no idea. I'd have thought it was an even number.
  • In "Zarak Mosadek", Reddington tries to inform the parishioners in a church that a gas leak is taking place. Seconds later, he and Dembe get into a firefight with armed men. He then later tells them that the leak is taken care of.
  • Red tries to teach a guy how to be a great Body Double in "Ian Garvey: Conclusion". It goes as well as you'd expect with wild overacting.
    • That's not to mention the sheer joy of watching James Spader and John Noble embark on Ham-to-Ham Combat.
  • In "Lawrence Dane Devlin", the taskforce finally meets Brimley, who brings a ferret along to interrogate a suspect who isn't talking. He and Red then spend several minutes explaining how the ferret in question is Hollywood trained, and how she's guaranteed to get the information they need... then Aram walks in, having gotten the information on his own.
  • Red is dropping in on a suit maker contact who just happens to be doing a suit for John Waters. It turns out Red is a huge Fan Boy and gushes to Waters on his films while they trade compliments on their outfits.

    Season 6 
  • The season opens with a bank robbery, which quickly goes sideways as it turns out that Red and Dembe are also there, scouting out the bank for their own planned robbery. Red then spends several minutes criticizing the robbers' technique, before making them hand over half their haul (on top of the deposit box he came to steal) in exchange for helping them escape.
    • During the resulting car chase, Red seems genuinely disappointed that the robbers open fire on the chasing police, before casually causing the bed of the garbage truck they're riding on to lift up and dump them on the street.
    • Then, Red returns to the bank the next day, returning the deposit box and the valuable stolen painting contained in it with orders to return the painting to its proper owners. When the manager incredulously asks why he bothered doing all this, Red cheerfully responds that it was a test of himself to see if he's still got it despite pushing 60.
  • Red and Dembe doing Tai Chi with a group of senior citizens.
  • While normally a tense scene, the UN bomb defusal scene during 'The Corsican' has a few worthy moments:
    • Max's solution to opening the bomb case? Freezing the lock and literally smashing it with a hammer, praying that it doesn't go off. Liz's expected shock and Red's initial glee followed by a Screw This, I'm Outta Here! moment are what changes the tone:
    Liz: (upon seeing the hammer): What are you going to do with that?
    Max: I'm going to smash the lock, whack it to pieces and pray that opens the case.
    • After Red just leaves Liz with Max to explore the UN, he ends up at the General Assembly and makes a speech on the main podium that quickly veers right into Large Ham mode, being mostly about extolling the virtues of one of the world's unsung heroes — Cary Grant.
    • When the bomb is successfully defused, Ressler of all people is the first to swipe Max's flask and take a drink.
  • Raymond Reddington, the most wanted man in the United States for over 25 years, a criminal genius of the highest order, a man who has cheated death countless times and a master of escapes...is arrested by a trio of regular patrol officers. On a New York street corner. While buying a pretzel.
  • Aram tells Liz and Ressler that "he's been arrested." They assume he's talking about the would-be bomber and how they're happy with Aram confused. "I know he's a killer but still..."
  • Red is completely blatant about offering his arresting officer a massive bribe via secret bank account to let him go. He's actually amused the man refuses and so leaves his autograph "to sell on Ebay."
  • Liz has an Elevator Action Sequence with a suspect in a hotel, which is momentarily interrupted by a cut to an elderly couple waiting for the same elevator. Afterwards, the couple mention that they're not going to the hotel ever again after seeing Liz aim her gun at the suspect.
  • Red warns the therapist about to administer him a Rorschach test that all ink blots look like genitals to him. He then takes one look at the first ink blot and laughs.
  • It's black comedy but still funny that Red went to the trouble of having himself put in a mental hospital just so he could meet with an old contact on vital information....only to discover the guy is on so many meds that he's in an open-eyed coma. Red's "oh, for the love of..." face is priceless.
  • In "General Shiro", Red enlists Dembe to talk to Glen and find a suitable jury for his trial. At the juror interviews, Red dismisses several candidates for a range of reasons (such as one for loving pugs). The caper of this scene comes when one of the candidates is revealed to be none other than Glen himself, with the look on Red's face when he realizes sealing the deal.
    • During a recess in the interviews, Red and Glen have a phone chat, with Red angrily chewing Glen out over putting their plan at risk, ends with Glen cheerfully hanging up on Red, who hands the phone to Dembe in disbelief.
    Red: I may just ask the judge to let me go lie down in traffic.
    • During Glen's interview, the prosecutor quickly gets tired of his aggravating attitude and tries to dismiss him, only for Red to claim that his personality makes him perfect for the jury... all while giving him a “The Reason You Suck” Speech while he's at it.
    • It looks like Glen is about to get on the jury until his big mouth reveals he was once convicted for using loaded dice to win a fortune in Las Vegas and he's dismissed.
    Glen: Come on, you can't have a bunch of pocket protectors on this jury! This is Raymond Reddington!
    D.A.: I thought you said you didn't know who he was!
    Glen: I don't! Not Biblically! I don't roll that way!
    • Before all of that, Red is making demands for his jury that include full-scale essay questions on obscure authors and composers. And when he says that any potential juror who likes Schumann is a "philistine", the judge reveals that she likes said composer, including having had one of his pieces played at her mother's recent funeral.
    Red: (Beat as he realizes he just insulted the judge) ...My condolences.
  • Liz and Red's fellow convicts can't believe Red is so easily up front on breaking out of prison in just a day and treating it like it's a simple errand.
  • During 'Bastien Moreau', Liz makes it clear to Cooper that robbing the Luxembourg bank is down to her and Dembe alone and not to tell the other Task Force members. As soon as she steps on the jet, she's somehow surprised to see everybody else there anyway and realizes that, yeah, Cooper told the other members.
    • In the following scene, Red is approached by an attorney to sort his legal affairs and what to do with his body after the execution. As it turns out, Red has already made arrangements to be cremated and placed into opium pipes, quipping that if there is an afterlife, he'd want to be there high.
  • Ana tells Red there are conditions to his stay of execution.
    Ana: You will not beat, kill or torture anyone for 48 hours.
    Red: As long as I'm not alone in a room with you, I should be fine.
    • Red describing his first STD after getting his stay of execution from Ana:
    Red: It was pubic lice. Crabs. Caught them on Hammamet Beach in Tunisia. She was a Vassar girl traveling with a bunch of pals from the French house. Two years after graduation, and they were still making up for lost time. My God. What a weekend. But like you, they get right in there and feast away without mercy until you want to douse the whole area with kerosene and set the little varmints on fire. Sorry. You and the crabs, not the Vassar girls.
  • Red and Dembe break into a source's house during a game of Head's Up with the neighbors. While Red interrogates the guy, Dembe...actually plays along with the game.
    • The sight of the duo leaving with smiles as the guy's wife and the neighbors just stand there, wondering what the hell a wanted fugitive who should have been executed was doing there.
  • After Ana McMahon takes the role of overseer of the Task Force, Cooper expresses his joy. As he points out with his trademark smile, he wants her to take the job because of the unusually high mortality rate that comes with it.
  • During Red's party to celebrate his escape from prison, Glenn apologizes for screwing up the jury selection scam, before mentioning that his mother is also at the party and has always had a thing for Red. Red's facial expression sells it.
    • Brimley is also at the party, but isn't enjoying it because of the noise.
    Red: Perhaps you'd be more comfortable out on the veranda.
    Brimley: Miranda's over there.
    Red: No, no the balcony.
    Brimley: Forget it, I'll be out on the veranda, I can't hear a damn word you're saying.
  • The Blacklister of the week is Red's old mentor, Robert Vesco, who taught him everything he knows about being a criminal... and then robbed him blind. When Ressler hears about this, he says with a grin that he likes the guy already.
    • Red and Vesco team up to steal some pirate gold hidden beneath an opera house, with the opera itself as a distraction. Everything is going fine, until Red's explosive guy gets distracted by some intense memories triggered by the music, breaking down sobbing. Red is incredulous at this.
    • Red figure the only thing to do is call Glen and have him "create some noise." Glen's solution? March on stage to announce a grease fire and pull the alarm.
    • Red's utterly dumbfounded reaction to realizing that Vesco stole all the gold, swindling him again. Liz, by contrast, breaks out laughing.
  • Red's way of getting a contract killer to talk? Having him brought to a warehouse and a very hungry boa constrictor wrapped around him.
  • Red listens to podcasts...on audio cassette.
  • To help the team, Liz asks Red to contact that hacker "whose mother hates you."
    • The kid is at his prom and distracted by the DJ's music while trying to help Liz hack a system.
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