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As a Moments subpage, all spoilers are unmarked as per policy. You Have Been Warned.

An Opera Of Fear (Venice)

  • If you get caught by Octavio in the mission "Octavio Snap," instead of having his guards attack you (which most villains would do if they catch you, failing the mission), he instead is disappointed and unamused that he caught you:
    Octavio: I've got a shadow, huh? You stink! Back in my day, thieves knew how not to get caught!
  • In the first mission to infiltrate Venice Police HQ, when the lights are going haywire and Sly must hide under the tables, the ape mercenaries at the meeting can be heard saying some pretty funny things:
    (lights on)
    "Let there be light!"
    (lights off)
    "Oh, come on."
    (lights on)
    "I can see, da! I can see!"
    (lights off)
    "Make up your mind already."
    (lights on)
    "You look a lot better in the dark, Pietro. Seriously, you are an ugly, ugly man."
    • And then later Sly's distracting the mercenaries and Inspector Fox so Dimitri can escape:
    Sly: Hello assorted meatheads! And lady. Anybody feel like some exercise?
    Carmelita: Cooper?! Grab him, men!
    Sly: Aaaaand I'm out.
    • Even funnier when you have the chase with Carmelita, and you realize that the mercenaries don't follow her outside.
  • For one mission, Sly has to take over guard duty in disguise so Bentley can sneak into some coffee shops. During one of the post swaps, the guard on duty thanks Sly for taking over as his mom is cooking spaghetti. He mentions that it's so good that he wishes to be buried in his mother's pasta sauce, to which Bentley reacts somewhat dumbfoundedly:
    Bentley: Yeah... that's, uh, that's strange.
    • As Bentley's doing his work inside the shop, Sly prattles on about how he must be missing out on something if he's never had food that good, up until the point Bentley completes his work and exits the shop. Bentley gets annoyed and urges Sly to focus on the job, to which he agrees. Sly then adds that they should go get something to eat afterwards.
    • From the same mission, at the first stop:
      Bentley: I can't believe that worked! You've got the worst Italian accent I've ever heard! No offense.
    • Also in the same mission
      Sly: You know, maybe there's a good Italian restaurant around here.
      Bentley: Enough with the sauce! Keep your focus, we're on a job here. Thugs everywhere, death around every corner!
      Sly: You're right. We got one more coffee house to hit, then we're done.
      Bentley: Yes, now you're talking sense.
      Sly: And then we eat.
  • From "Run 'N Bomb", there's Sly's hilariously bad threat to Octavio after the rogue opera singer takes Bentley hostage:
    Sly: Put my friend down, or I'm gonna knock out all of your teeth, one at a time. And make you eat 'em.
  • The entirety of the opera duel between Bentley and Octavio. Bentley just horribly repeats "la" at different pitches, and if you lose, Octavio says that he can't go on because you're too awful. Furthermore, the song ends with an absurdly-high, Incredibly Long Note held by Bentley.

Rumble Down Under (Australia)

  • Before a mission where the Cooper Gang has to act tough to intimidate the local miners, Bentley asks his teammates how they can just "get angry." The response?:
    Murray: Find the match, deep inside yourself... light it, and let the fire burn up your guts and BOIL YOUR BLOOD!"
    Sly: Uh... yeah. I pretty much do the same thing.
  • "We here are known around these parts for our drinkin' skills... and this just happens to be... a lemonade bar."
  • "Bentley, I could use some help! How about putting a few of your sleep-darts in 'Carme-large-a' here?!"
    • Later, this exchange:
    Sly: You got a better idea?
    Murray: Yeah! But we'd need a giant fighting robot.
  • The gang having fun with Carmelita's camera while she's unconscious. The photos are hilarious.
  • In order to defeat a magically-altered and gigantic Carmelita, Sly must climb up her clothes, twice! As Bentley stated, can't get much closer.
  • Sly's reaction to the fact that the Miners had booby trapped the Guru's walking stick.
    Sly: Another booby trap for a stick!?! These guys are paranoid.

Flight of Fancy (Holland)

  • How the opening cinematic for this episode ends. Penelope revealing her avatar: it's the body of a beautiful woman with her real head taped on top (if you look closely, you can even see the remains of a "hello" wave that she failed to crop out). And Bentley has the same thing with his face taped over some muscular hunk's body!
    • Which is then referenced when they see each other for the first time and Sly comments on how their avatars were a bit... exaggerated. The cutscene makes a point of showing them staring blankly at each other.
  • Bentley warns Sly that the hotel is a no-fighting zone for the pilots, to which Sly remarks how everyone plays nice until tomorrow, "then we blow each other to bits at 300 feet".
  • When Sly asks Dimitri for info on the dogfight competition's secret roster, Dimitri refuses to talk because he is afraid of the Black Baron finding out about it. How does Sly convince Dimitri to help him? By telling Dimitri that he can outsmart the Baron... since Dimitri has the best fashion sense of anyone he knows.
  • Bentley needs to pick a fight against Muggshot so Carmelita can send him to jail. The insult that triggers it?
    • Before he snaps, Muggshot can tell Bentley not to say anything if he didn't have anything nice to say at all. In response, Bentley remains silent for several uncomfortable seconds. Muggshot is dumbfounded and legitimately hurt:
      Bentley: You know, I've been thinking about your appearance.
      Muggshot: Look, if you don't got nothing to say nice, then don't say nothing at all. Get it!?
      Bentley: ...
      Muggshot: What, ain't got no sassy comments, smart guy?
      Bentley: ...
      Muggshot: Oh, I get it, you got nothing nice to say so you're keeping quiet. That's real cute.
      Bentley: ...
      Muggshot: (looking concerned) You really don't got nothing nice to say?... That's cold.
    • This YouTube comment gives a good insight into Bentley's thought process:
      "It's as if Bentley is running out of "smart" insults to tick off Muggshot, and with Muggshot getting tired of it, thus forcing himself to resort doing a "your mom" insult, and I love it."
    • Sly tricking Carmelita into chasing him as part of the above plan:
    Sly: Hey, Inspector Fox! Still looking for a date to the prom?
    Carmelita: Quit running, and I'll pin the corsage on you!
  • One of the missions involves getting Murray to make one of the Belgian pilots laugh. While the one option that works (physical humor) is still great, if you try all the others you'll get some real So Unfunny, It's Funny gems. Murray's attempts at jokes are downright surreal.
  • There's a giant wolf roaming the landscape. Fights between it and the guards tend to result in the wolf winning... it's also pretty likely that you'll be minding your own business and suddenly the wolf's trying to eat you.

A Cold Alliance (Kunlun Mountains, China)

  • Penelope's reaction to Murray asking anyone if they want to see his blisters.
    Penelope: No way! Is he serious?
  • When the gang first comes to recruit the Panda King for their heist, they at first find him too lost in meditation to interact with by normal means. As such, Sly and Bentley discuss possible solutions:
    Sly: Let's just shout in his ear.
    Bentley: No, to break him out of this trance, we'll need to delve into his mind.
    Sly: A hacksaw, then?
    Bentley: No!
  • During the mission to destroy a crypt of hopping vampires, Sly tries to hype up Panda King for what's to come. It's incredibly forced, which both parties recognize:
    Sly: There're gonna be fangs everywhere!
    (Panda King just stares at Sly, blankly.)
    Sly: Right... I'll head back to the safehouse.
    (Another pause.)
    Panda King: Yes, do that.
  • When Panda King talks to his other half on working with Sly and the gang. When his bad half keeps refusing, Panda King convinces him with this:
    Panda King: If strength were all that mattered, Tsao would be an ideal son-in-law.
    Inner Panda King: (without hesitation) Very well, Cooper shall live.
    • There's also this afterward:
      Panda King: Fear not, Cooper. I shall not kill you today.
      Sly: Um... ditto.
  • One mission has Penelope instruct Murray to break open a strongbox, which turns out to be a trap that sprays him with Knockout Gas. Murray's reaction before falling unconscious?
    Murray: OHH, KOFF, HOOGH-! That's... bad... gas!
Dead Man Tell No Tales (Blood Bath Bay)
  • Sly's attempt at a pirate accent.
    • On that note, the pirate insult competition. They refer to it as cursing. Well, they're G-Rated pirates.
      Sly: You're a brainless, clam-tongued, waste of skin!
      Pete: That be true enough, but you're a stupid, scurvy-ridden, cabin boy!
      Sly: You are a pin-headed, cross-eyed, piece of filth!
      Pete: Har, har! But methinks you're a blathering, grog-abusing, whale-fart!
      Sly: You're a donkey-eared, barnacle-backed, cow pie!
      Pete: Ha! Yah swear like a child! You're a bleating, yellow-bellied, bag of vomit!
      Sly: You're an idiotic, pus-faced, sack o'maggots!
      Pete: That be true enough, but you're a cricket-sized, twisted, anchor-head!
      Sly: Oh yeah? You're a pig-breathed, knuckle-dragging, swabber!
  • Bentley attempts to speak Dimitri:
    Bentley: Cool, Daddy-O. How 'bout you take your "pimped self" down 'neath the H20, and get nasty with the scuba... yo, with bling.
    Dimitri: Hey man, you can try, but you'll never capture my essential style. It's like smoke, ungrababble and all over the place! But no matter, no thing, come at me with some turtle talk. You've got your own flavor.
    • And Bentley does it again when Dimitri finishes the mission! Except here, Dimitri doesn't bother talking him out of it.
    Bentley: Magnificent, bro! Your method and madness have cold set us up with a fat pirate gat. You're a solid gold all-star on the Team Cooper label!
  • LeFwee might be a chauvinist Jerkass who flagrantly toes the line between Faux Affably Evil and Smug Snake, but he has some very funny lines.
    • While being forced to walk the plank, Sly tries to get LeFwee angry in front of his men. For the most part, LeFwee is hilariously unconvinced.
    LeFwee: (on the fact that his plank has splinters in it) Oh now, I take a great deal of pride working a bunch of splinters into the feet of all about to walk my plank! Har har! 'Tis the extra touches that makes all the difference.
    Sly: "Slanderous scabbard?" I could do better in a coma, while speaking another language, to deaf apes!
    LeFwee: Hmph. Your word-smithing is preposterous, presumptuous, patently premeditated!
    • Oh, and the guy even sneaks in a sexual innuendo for good measure.
      LeFwee: I'd never have a problem with the ladies, especially when I've a broadside aimed at their sailboat... Savvy?
  • During a mission with Penelope, Bentley expresses some frustration over not being capable of the athletic feats Sly can do. When Penelope tries to reassure him by saying that Sly can't "rewire a satellite or write ASCII code," Bentley dryly retorts that Sly can't even spell ASCII.
  • The ending cutscene for this episode has Carmelita not appear. Sly's response?
    Sly: Oh well, I'll just send her a postcard. (cue a postcard with the group in a conga-line, Sly with a Pirate hat and eyepatch on, Panda King with an unamused frown, and the Guru on the corner of the postcard that's signed, "Wish you were here" - Sly)

Honor Among Thieves (Kaine Island)

  • Before Dimitri is about to go diving during the Cooper Vault heist, he tries flirting with her:
    Penelope: Okay, first: get over yourself. Second: I mean it, get over yourself!
  • This exchange:
    Murray: Nice! We'll have the Panda King give the van a boost! Stand clear Sly, we're about to get awesome!
    (Panda King lights the fireworks)
    Panda King: (Gleefully) The fuse is lit!
    Murray: Buckle up, Bentley... we're about to fly!
    (The van shoots up into the air)
    Murray: YAHOO!
    (The van lands at the entrance to the Cooper Vault)
    Bentley: We're never doing that again.
  • During the "Beginning of the End" (In Medias Res) intro mission, Sly exclaims that Dr. M should "buy a knock off at the gift shop" after the latter tries to steal Sly's cane. In this final episode, when you return to the vault, there are piles of knock-off canes in front of the vault. Apparently, there WAS a gift shop.

Other

  • The insults Bentley slings when he's using his grapple cam. Most of them are the kind of insults you'd only expect a child to react to!
    "Over here!"
    "Hey, fatty!"
    "Come over to this position!"
    "Follow the sound of my voice~"
    "Yo, ugly!"
    "Yo mamma!"
    "Eat dirt!"
    "I'm yelling at you!"
    "Hey, pay attention to me!"
    "You're a bad person, I mean it!"
    "Up your nose with a rubber hose!"
    *Clucks like a chicken*
    "You! With the low self-esteem!"
    "I'm right here!"
    (singsong) "You will never find me!~"
    "Aloha, idiot!"
    "Hey, you! Unattractive person!"
  • The unlockable video "The Evolution of Sly", which shows early footage of Sly 1 and 2. While it's interesting to see what the games looked early on, the devs also consider a lot of things Old Shame.
  • Whenever Carmelita Fox shows up, it’s possible for her and the local goons to end up in a fight. Grab some popcorn and watch the fun — from a safe vantage point of course. Don't worry — Carmelita wins these fights.
  • During the "Where Are They Now?" Epilogue, we get a few gems:
    • Anime fans might recognize Murray’s racing pose.
    • Panda King retires and moves two doors down from his daughter. At her insistence, he personally screens her future suitors, and so far Jing is still unmarried. Turns out having a stony, short-tempered Pyromaniac for a dad can really put a crimp on your dating life.
    • The Guru takes on some celebrity disciples (who just happen to be the same Beatles expies who upstaged Octavio), drawing in a lot of unwanted publicity. To escape the paparazzi, Guru decides to move his teachings to Central Park, New York, thinking it’d be the last place they’d ever look.

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