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

Police Headquarters (Paris)

  • The first lines of dialogue between Sly and Bentley, establishing their dynamic for the game:
    Bentley: (shouting) Sly! Come in! Sly! Do you read me?
    Sly: Yeah, I read you. Loud and... very loud.

  • There's a bunch of empty rum bottles scattered around Inspector Carmelita Fox's office. Even before we first meet her, we can tell just how hard she's been taking her failures to catch Sly.

  • Sly and Carmelita confront one another before Sly interrupts himself to say that Carmelita's shock pistol brings out the color of her eyes.

Tide of Terror (Isle O'Wrath)

  • This conversation between Sly and Bentley when you first approach a machine wheel:
    Bentley: Sly, see that machine wheel? If my knowledge of mechanical engineering serves me right, applying significant rotational torque to achieve maximum velocity should yield a positive result.
    Sly: You mean something good might happen if I get the wheel to spin fast enough?
    Bentley: Isn't that what I just said?
    • On that note, there's this exchange, which probably does a better job of summarizing their dynamic than the Police Headquarters example above:
      Bentley: Do not forget, Sly, you have to get close...
      Sly: ...Then press the circle button to grab [the ladder], yeah, yeah, yeah. Relax, Bentley. I live for this stuff.
      Bentley: Yeah, and that's what worries me.
  • Forget engineering or piracy, Sir Raleigh's specialty is Chewing the Scenery like a spoiled and demanding king:
    • When Sly first reaches his hideout:
      Raleigh: (over intercom) I say, chaps, my heartiest congratulations to you all! The storm machine has sunk its fiftieth ship last night, and the loot has already been unloaded! Our operation is moving along splendidly, with the possible exception being... the gross NEGLIGENCE displayed below decks, and... I demand the boilers stay at full pressure at all times! If you lazy, low-brow, technically incompetent pack of guttersnipes DID YOUR JOBS RIGHT, WE'D HAVE SUNK A HUNDRED SHIPS BY NOW! (calmly) ...But of course, fifty boats is a fine, fine achievement. Carry on, my boys, carry on.
    • After Sly's stolen most of the treasure keys, his second intercom announcement in "The Gunboat Graveyard":
      Raleigh: (over intercom, clearly attempting to hold back his frustration) Ahoy, dock hands! Capital job unloading that cargo last night. You're the crown jewel of my operation. Do me the service of proving your worth yet again by protecting the treasure key that I have stored down there. It appears there's a prowler on the premises. And if any of you... let him get his hands on that key... I'll personally flog the lot of you... FOR AN ENTIRE FORTNIGHT!
    • And last but not least, his confrontation with the raccoon himself:
      Raleigh: (upon being confronted by Sly) Obviously, we should have snuffed you out as well. So, without further ado, let me make amends by, what... BLOATING TO GARGANTUAN SIZE, AND SQUASHING YOU LIKE THE INSIGNIFICANT BUG THAT YOU ARE!!!

  • Following Raleigh's defeat and arrest, the Isle of Wrath is renamed the "Isle of Nice".

Sunset Snake Eyes (Mesa City)

Vicious Voodoo (Haiti)

  • Regardless of its That One Level status, "Down Home Cookin'" takes place in a barn, where it turns out one of the ghosts that had been scaring you earlier just wants to make some gumbo, but is scared of the bomb-toting roosters.
  • You know how you do a typical boss battle with the Arc Villain of the episode four out of the five times? Guess which one is the odd boss out? Mz. Ruby! Her boss battle is a rhythm-based minigame (or at least, it's supposed to be) where you have to time your button presses in tune to the music. It's sudden, it's weird, and it's oddly hilarious.
    Sly: Dig-that-voo-doo!

Fire in The Sky (Kunlun Mountains, China)

  • While the idea of Panda King burying villages who don’t pay for his "avalanche protection service" in avalanches is horrifying, it does lead to a humorous Genre Savvy moment during his announcement afterwards.
    Panda King: Attention, valued employees. Sadly, Hikam Village did not pay for avalanche protection service, and so I am forced to bury them alive under many tons of snow. Please be on lookout for any surviving villagers who come looking for revenge. Thank you, that is all.
  • Should Sly manage to unlock all the vaults up to this point, he'll unlock the "Meeting the Ancestors" trophy. Now, what does Sly do in Sly 4? Oh, he actually meets up with a number of them.
  • During a segment where Bentley is trying to crack the cypher on a map leading to Clockwerk's base, he remarks that the cypher itself isn't the problem; It's that not only is the dialect difficult to parse, presumably because Clockwerk applied the cypher to his native Russian, but because his penmanship is atrocious. Of course, since Clockwerk is a gigantic owl with no hands to speak of, the idea that he wrote it to start with is its own form of comedy.

The Cold Heart Of Hate (Krak-Karov Volcano)

  • During the final phase of the battle against Clockwerk, the giant scary owl who was a pure Knight of Cerebus just prior lets out odd non-sequiturs as his body is auto-repairing itself.
    "I am... selling... flowers..."
    "Feet together!"
    "Shift F5, shift F7, F5 will live."

Ending

  • Carmelita gives Sly a ten-second head start as a token of gratitude for rescuing her, but he spends the whole countdown staring at her with a smug expression. As she reaches zero, he gives her a kiss on the lips. Carmelita then just has a dazzled expression of "Wow, what was THAT?"... up until she realizes that Sly's handcuffed her to the railing.
    • The "anime" version of the ending adds an extra detail: Sly uses his cane to grab her arm, prompting Carmelita to make a split-second expression of shock before the Kiss of Distraction.
  • As imposing as the Sequel Hook Cliffhanger is, Murray's "Oh no" reaction to it combined with a stock scream is rather amusing.

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