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

  • In general, the improved in-game animations can get you a laugh due to them being more clear and expressive, even during simple Binoc-u-com conversations. There are more than a few examples, but one of them might just be Sly's baffled, open-jaw reaction to El Jefe's statue.

I Smell A Rat (Paris Prologue)

  • The main characters are all given titles when they're revealed in the prologue (Sly the Thief, Bentley the Brains, Murray the Muscle). When Carmelita, who's caught Sly in the middle of stealing something, shows up, it reads "Carmelita the Girlfriend"... before a red X crudely crosses out the "Girlfriend" bit and changes it to "Carmelita the Ex-Girlfriend."
    • And after Sly makes his daring escape out the skylight, he pops his head back in to say, "I'll call you!" while making the appropriate hand-gesture. He has to duck to avoid being shot by Carmelita.
  • "Welcome to Air Murray. Thanks for flying!"note 
  • During the animated scene where the Cooper Gang gives Dimitri the Thievius Raccoonus, Dimitri decides to give Bentley an incredibly garish and sparkly hat. True to form, Sly snarks that the communicators would limit the gang's exposure to Dimitri's fashion critiques.

Turning Japanese (Feudal Japan)

  • The following remarks from Sly's first meeting with Rioichi Cooper, who's locked in a cage.
    Sly: Just stay put.
    Rioichi: Very funny.
  • Bentley's attempts to give Rioichi pre-mission tutorial advice like he usually does with Sly lead to no impact whatsoever, as anything Rioichi responds with can be best summarized as "I'm an experienced ninja and I already live here, I know how to do my job", with the look on his face saying "Get to the part where you shut up, please."
  • Murray dressed as a Geisha. That is all.
    • Not to mention the guards going completely gaga over his performance as "Madame Geisha," complete with Tex Avery-style Wild Takes. All the while, Rioichi is popping up around the shot during the performance cutscenes, with an expression of "are you freakin' serious right now?", mixed with heavy amounts of Squick.
    • There's one point where Rioichi is standing right in front of them, waving his hand in their faces, and they still don't see him because they're too transfixed on Murray's act as "Madame Geisha."
    • If you do the rhythm game perfectly, even Rioichi is transfixed by Murray's dancing.
    • Fail this dance (rhythm game) and you get a hilariously catty remark out of it.
      Job Failed Alert: That dancing stunk worse than rotten sushi!
    • He'll also remain in that outfit for as long as the Gang's in Japan, and wears it for the assault on El Jefe's fortress. And it is glorious.
  • "'El Jefe'? Isn't that Spanish for 'Big Baby'?"
    • On that note, get too close to El Jefe before he's vulnerable and he'll give you a full-on slow-motion Shoryuken in response.

Go West, Young Raccoon (Cotton Mouth Bluff)

  • A subtler moment: Bentley tries to use cowboy language to sound cool. Sly, with his trademark smirk unchanging, just tilts his head and quietly shrugs when Bentley tries explaining it.
  • Sly's defacing of Sheriff Toothpick's posters has to be the funniest act of vandalism you've ever seen. And he knows it, giving the posters serious, artsy names like they're actual artwork. Listen close enough and you can even hear him corpsing a couple times.
    Sly: Not for sale! It's "Puny Green-Horn"!
    • When pickpocketing Toothpick's Cuban rice-and-bean-flavored lollipop, Sly's expression is a straight face as opposed to his usual smirk. He's then curious as to whether to give it to Murray.
    • The fact that not only did Bentley expect nothing more than a load of petty vandalism to be enough to get Sly chucked headfirst into Toothpick's maximum security prison, but it actually was.
    • The "Job Complete" screen has Sly quietly accept his new Jailbird costume until the ball and chain lands on him. The dejected expression he makes is gold.
  • While Sly is breaking Tennessee out of prison, Sly starts talking to Bentley. Tennessee is understandably confused.
    Tennessee: Son, who is it you keep talkin' to?
    Sly: Uh, I have a thing in my ear... that lets me talk to my friend. And now he's telling me you need to carry some of that TNT so we can blow the gate.
    Tennessee: Sure. Ah got voices in my head tellin' me to blow things up, too. Heh, they been right so far! Let's get to it!
    • And another, more grim-yet-funny exchange during the prison break:
      Sly: Why am I the only one with a ball and chain here?
      Tennessee: Listen, friend. They're plannin' on hangin' me tomorrow. Wanna trade?
    • Sly and Tennessee escaping the prison by paraglider? Cool. Sly creating the necessary momentum for both of them by kicking Tennessee off the edge of the cliff the prison is on? Funny.
      Sly: You ready?
      Tennessee: Well, er, not really.
      (Sly kicks Tennessee off the cliff, grabs him and opens the paraglider, with Tennessee going from screaming to... yee-haw-ing)
  • Later into the episode, Bentley gets rather attached to his disguise and in particular the fake mustache, leading to him lamenting the fact he can't grow a real one and this line:
    Sly: You're not going to start wearing that mustache all the time, are you?
    Bentley: Jealousy is such an ugly emotion, Sly.
  • While bugging Toothpick's office, you see him accidentally shoot one of his goons, and his reaction is basically to just go "Uh, oops."
  • After rescuing Sly and the others, as Carmelita and Tennessee, during the escape, the group jumps onto some unconscious mooks. Said mooks make a squeaking noise as they are jumped on.
  • Before Sly goes racing to obtain a key, Bentley tells Sly he needs to use his ball-and-chain to complete the race:
    Sly: Good idea, because you know...
    Bentley: Don't say it!
    Sly: (cuts to gameplay) That's how I roll!
  • During a shooting competition to get a key, Carmelita may say this:
    Carmelita: It kind of helps if I picture Sly's face on the target.

Clan Of The Cave Raccoon (Gungathal Valley)

  • The intro scene has Sly see a pterodactyl fly by. What does Bentley do? Break out an anti-pterodactyl cannon.
    • Sly calls it the dinosaur repellent.
  • The very first time you see The Grizz in Gungathal Valley. Imagine walking through a prehistoric world and then all of a sudden you're encountered with one of the strangest and most out of place characters in the entire series.
  • This exchange:
    Sly: Hey Bentley, why don't we have a phone like that to talk to Dimitri?
    Bentley: Do you really want Dimitri calling you?
    Sly: Good point, forget I asked.
    • The Grizz's phone reception constantly failing, with him growing increasingly frustrated.
    Grizz: You're choppy... You're choppy... You're choppy!
  • How the gang finds out Bob's name.
    Sly: Uh, my name's Sly. Sly Cooper. What's yours?
    Bob: I am called ...gibberish... .
    Sly: Riiiiight... How about I just call you Bob?
    Bob: Sure, whatever. Now can we get out of here before more guards show up?
  • The animated clip that showed Bob Cooper's past. This includes:
    • Him finding the communicator and chewing it. In fact, he runs off while Sly just shrugs his shoulders.
    • He carries Sly back to the hideout by his collar.
    • He downs an entire cherry pie in front of Murray.
    • The crayon-like drawings that explain The Grizz snatching eggs.
  • If you get caught by The Grizz when you're tagging him with homing darts:
    Job Failed Alert: Nobody fools with The Grizz!
  • Bob finds the time machine's missing temporal sprocket with the "Job Complete" cutscene playing... just before getting attacked by a giant pterodactyl who promptly steals said temporal sprocket.
    Bentley: Well, that's not entirely surprising.
  • In one mission, Murray has to retrieve the stolen parts of a time machine gadget. How? By chasing down penguins, catching them, and squeezing them until they cough it up. Complete with squeaking sound effects!
  • The mission "Getting Stronger." All of it. Mainly for Murray's one-liners.
    • To elaborate, they need to get Bob in shape. Murray's way of doing this is to put Bob through an eighties-style training montage, complete with appropriately cheesy 80's and scene transitions... which is technically the very first of its kind, given that the crew is in the Ice Age when doing it!
    • Failing any of the minigames during the practice run in this mission will result in the game really kicking you when you're down with quotes that wouldn't be out of place in the Henry Stickmin Series.
      Job Failed Alert (Slippery Slope): You cracked under pressure.
      Job Failed Alert (Penguin Popper): You don't want it bad enough!
      Job Failed Alert (Super Sling): Your hardest target is success.
      Job Failed Alert (Duck and Cover): You're moving in slow motion!
      Job Failed Alert (Whack-a-Chump): Maybe you should try it with your eyes open next time!
      Job Failed Alert (Sumo Slap): What a pushover!
  • Just the fact that one of the missions was called "Ice Ice Bentley."
  • When Carmelita argues with Sly after a mission about how Sly could have done better, you can see Bob in the background looking back and forth at the two in either curiosity or knowing.
  • An amusing reference upon Murray arriving at The Grizz’s lair:
  • Murray's confused reaction to the Grizz saying that all he ever wanted to do is ice skate.

Of Mice and Mechs (Medieval England)

  • Sir Galleth being very gung-ho. In his animated cutscene, he tries to escape through a door, but Sly stops him. So he tries going through a window... and gets pulled away by Bentley, Sly, and Murray in a large chain.
    • Before that, the portion of the cutscene that explains how Sir Galleth was captured in the first place. Just after fighting his way to the Black Knight, Galleth lunges at the Black Knight... only to get popped. Bonus points for the punch being seen from Galleth's perspective and for Galleth's cane and helmet being the only things shown hitting the ground.
  • If you get caught by the Black Knight at the beginning of "Shell Shocked Heart," you can get a rather funny line from Bentley.
    Bentley: Sly, I said "tail," not "fail"!
  • While tailing the Black Knight, it's possible to hear this gem.
    Black Knight: I wonder if I can program one of the guards to give me a haircut. On second thought, that's probably a really bad idea.
    • Of course, given the identity of the Black Knight, it probably would have been more of a close shave.
  • Compared to his classic leg twitching or just looking around, Sly's idle animation for his Archer Costume is using it as an air guitar.

40 Thieves (Ancient Arabia)

  • Salim Al-Kupar has an ''enormous'' appetite. In fact, he downs a giant chocolate cake that Murray was about to eat in one gulp (and also gained a Balloon Belly to boot!)
    • When Sly first meets Salim, Salim is unwilling to join the team... until Sly mentions that they have food back at the hideout. Salim is immediately right next to Sly, and his reaction is basically "didyousayfood?"
  • Similar to the phony "Job Complete" cutscene from "Clan of the Cave Raccoon," when Sly obtains Salim al Kupar's thief outfit, there's a guard in the background during the Item Get! cutscene. You might think this is a goof, but then he actually attacks Sly (and is promptly smacked down with Sly's newfound time-slowing powers).
    • Furthermore, because the shop where the costume is cannot be entered, Bentley comes up with the plan that, for one time, they will have to buy the costume legitimately.
  • While undercover wearing the Arabian thief outfit, Sly Cooper impersonates himself as the delivery boy and enters Le Paradox and Miss Decibel's tent. What's more, Sly Cooper talks to them with his trademark... Italian accent. Not only that - Sly manages to fool them, which leaves this remark from Bentley:
    Bentley: Sly, it's a good thing we're in Arabia, because in Italy, that accent would be considered a felony!
    • Don't forget Bentley's reaction to the fact Sly's using it:
      Bentley: I said "crazy," Sly, not "suicidal"!
  • Bentley explains that in order for them to get into the room where Le Paradox and Miss Decibel are inside, Carmelita will need to distract the guards... in a belly dancer outfit. Then this occurs...
    Bentley: However, since we don't want to announce our "presence," we need a diversion for the guards. So I have taken the liberty for fashioning an outfit for Carmelita, who will use it to lure the guards away from their post by performing a belly dance.
    Carmelita: What?
    Sly: Possibly your best plan ever, Bentley.
    Bentley: I'm sorry I didn't ask, Carmelita. But you're the only one who can pull this off!
    Murray: Um, Bentley... I could do it!
    Carmelita: I am not getting into that outfit!
    Bentley: I realize it's a bit... revealing, but think of it as going undercover.
    Carmelita: Bentley...
    Murray: I'm positive THE MURRAY can squeeze into that thing!
    Sly: Hey Carmelita, you should totally model that outfit for us... to make sure it fits!
    Carmelita: Shut up, Ringtail! I'm only doing it for the team.
    Murray: Listen! Silk is very elastic!
    • Murray really wants to cross-dress and go dancing ever since his "success" as Madame Geisha. And to make it funnier, during the above presentation, Bentley has placed a picture of the outfit Carmelita is to wear in his slideshow, placed on a mannequin. Murray proceeds to draw his head and hands over the mannequin's own.
    • As they reach the location, this conversation occurs...
      Bentley: Ok, Carmelita. We need you to distract those guards and get them away from that door!
      Sly: Yeah! Bust a move, Carmelita!
      Carmelita: How about I BUST YOUR FACE, Cooper?
      Bentley: We're counting on you, Carmelita! Meet us inside once you lose the guards.
      Carmelita: Bentley, you owe me BIG TIME for this one! *knocks his head*
    • Much like Murray's dancing stage, most of the time you hear Carmelita mumbling about Bentley's idea and her wearing a belly dancer outfit during her "distraction."
      Carmelita: This is the WORST undercover assignment ever...
    • Fail the belly dancing minigame and the game gives another funny quip.
      Job Failed Alert: That was more like a belly FLOP!

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