During the final portion of the battle against Clockwerk, he lets out odd nonsequitors as his body is autorepairing itself.
"I am... been selling... flowers..."
The Mercy Lead Kiss from the ending. Carmelita gives Sly a ten-second head start, and he spends the first nine staring her down. On the tenth, he gives the surprise smooch. After Sly plants a hot one on Carmelita, she just has a look of "Wow, what was THAT?" ...up until she realizes that Sly's handcuffed her to the railing.
From the Second Game:
Jean Bison's epilogue. He becomes a member of the EPA... and gets frozen again.
"You can run from me, but I know where you're going: Jail"
From the Third Game:
When Bentley challenges Octavio to opera singing, controlling Bentley is the funniest thing ever! When he actually sings, it's just him horribly repeating "la", and if you lose, Octavio says that he can't go on because you're too awful. But the best part of all, is that pressing the square button will make Bentley air guitar!
"Bentley, I could use some help! How about putting a few of your sleep-darts in "Carmelarger" here?!"
Later, this exchange:
Sly: "You got a better idea?"
Murray: "Yes, but we'd need a giant fighting robot."
The insults Bentley slings when he's using his grapple cam.
The gang having fun with Carmelita's camera. The photos are hilarious.
Penelope's reaction to Murray asking anyone if they want to see his blisters.
The Pirate insult competition. They refer to it as cursing. Well, they're G-Rated pirates.
Sly: Yer' 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!
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)
(The van lands at the entrance to the Cooper Vault)
Bentley: ...We're never doing that again.
The ending cutscene for "Dead Man Tell No Tales" 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 frowning, and the Guru on the corner of the postcard that's signed, "Wish you were here -Sly)
The last scene before the intro to Flights of Fancy? Penelope revealing her avatar: it's the body of a beautiful woman with her head taped on top. 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 mentions on how their avatars were a bit...exaggerated.
In a mission in Venice, Sly has to take over guard duty in disguise so Bentley can sneak in to 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, saying it's strange. As Bentley's doing his work inside the shop, though, 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 tells him to knock it off and focus on the job, to which Sly agrees. He then adds that they should go get something to eat afterwards.
From the same mission, at the first stop:
Bentley: I can't believed that worked! You got the worst Italian accent I've ever heard! No offense.
Before Dimitri is about to go diving during the Cooper Vault heist:
Penelope: "Rule number one: Get over yourself. Rule number two: I mean it, get over yourself!"
"I'm not your cheesy macaroni Sly Cooper! You got DIMITRIII-III!!!" *lights break*
Sly: "That is the last time that we leave Dimitri in charge of the hideout."
Bentley: "It was also the first time."
For the previews, anything that Sir Galleth says. It helps that he's a Large Ham.
Bentley: Do you see anything, Galleth?
Galleth: Aye, Bentley. I do forsee the wretched beast lay low by my blade!
The Gamescon 2012 trailer has one with Carmelita blasting a sword that Sly had in hand. What sells it is not only his expression, but also Bentley and Murray's... it screams "We are in ''so'' much trouble."
They really are, given the time machine runs off of artifacts from the era they need to travel to, and that tanto dagger was their only ticket back to Feudal Japan, if they needed to help Rioichi again. Not to mention possibly their only way home from the Old West.
GameTrailers's preview has a funny line: "With Sucker Punch in more Infamous projects"
The following remarks from Sly's first meeting with Rioichi Cooper.
Sly: Just stay put.
Rioichi: Very funny.
When it comes to giving the main characters titles (Sly the Thief, Bentley the Brains, Murray the Muscle), when it goes to Carmelita, it reads "Carmelita the Girlfriend" before crossing 'Girlfriend' off and it reads "Carmelita the Ex-Girlfriend"
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 the "job fail" sign will remark that the dance stinks worse then bad sushi.
From the Ice Age chapter:
Sly: Hey Bentley, why don't we have a phone like that to talk to Dimitri?
Bentley: Do you really want Dimitri calling you?
The Grizz's phone reception constantly failing, with him growing increasingly frustrated.
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 explains about The Grizz snatching eggs.
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?"
Sir Galleth being very gung-ho. In the 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.
While undercover wearing a 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!
In fact, this is actually a Call Back from the third game, as Bentley comments to Sly in Venice he has the worst Italian accent he ever heard... and STILL manages to fool everyone.
Don't forget Bentley's reaction to the fact Sly's using it:
Bentley: I said crazy, Sly, not suicidal!
While Sly is breaking Tennessee out of prison, Sly starts talking to Bentley. Tennessee is understandably confused.
Sly: Oh, er, I have this thing in my ear that lets my friend give me advice.
Tennessee: Oh, that's cool. Ah got voices tellin' me to blow stuff up too.
And another, more grim-yet-funny exchange during the prison break:
Sly: How come I'm the only prisoner who got a ball and chain?
In 40 Thieves, Bentley explains that in order for them to get into the room where Le Paradox and Miss Decibel are inside, Carmelita is doing a distraction...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.
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.
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 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! *knock 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 dance game and the "job fail" sign will said that's more like a "belly flop".
In "Go West Young Raccoon", 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 all the time are you?
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.
The intro scene to "Cave of the Clan Raccoon" has Sly see a pterodactyl fly by. What does Bentley do? Break out the pterodactyl cannon.
Sly calls it the dinosaur repellent.
Prior to the boss fight with The Grizz, we hear him explaining about how all he ever wanted to do...is ice skate. Murray's reaction says it all.
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).
Similar to the above, but using the "Job Complete" cutscene instead of "Item Get" cutscene, as Bob holds a temporal sprocket for the first — he is attacked by a giant pterodactyl who steals the temporal sprocket.
When Carmelita makes a comment after the mission before the Grizz boss fight 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.
Also from the Ice Age chapter, just the fact that one of the missions was called "Ice Ice Bentley".
If you get caught by the Black Knight at the beginning of "Shell Shocked Heart", you will get a rather funny line from Bentley.
Bentley: Sly, I said tail, not fail!
If you get caught by The Grizz when you're tagging him with homing darts:
Job Failed Alert: Nobody fools with The Grizz!
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 training montage, complete with cheesy eighty music and scene transitions.
"'El Jefe?' Isn't that Spanish for 'Big Baby?'"
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!
Sly's defacing of Sheriff Toothpick's posters has to be the funniest act of vandalism you've ever seen.
Sly knows it. He keeps giving the posters serious, artsy names like they're actual artwork.
The cartoon Timing is Everything has Sly finding Carmelita tied up and rips off the duct tape covering her mouth. First thing she does? Scream like hell. What does Sly do next? Start untying her, then stops before taping her mouth once more.