When Dr. M ask his subordinate Richard in the beginning of the game how were his wife and child, his subordinate happily answers they are doing well. Dr. M Then precedes to tell him he won't be seeing them again,as he has poisoned his drink, simply because he didn't change the security code from "123" after installing a new system. We then get to see the poor guy die a slow death. The kicker? After that Dr. M gets a call that water is leaking into his lab. He tells them that he'll be right there, and to bring a janitor up to the elevator. Because Richard's gotten "sloppy". Sly who's on top of the elevator hears the whole thing, and doesn't even blink an eye. Yep, that's within the first 10 minutes of a kid game.
Black Spot Pete calls Sly a "skinny, malodorous, hairy palmed bottom feeder"!
When Carmelita busts Muggshot, his last dialogue is "Mother...forgive me... I didn't know they was yours." Yeeeah.
After you beat Muggshot, Sly calls him a "canine steroid case."
You go looking for Murray in Italy, starting with the local police HQ. Sly sneaks in and makes it to the jail cells, running into Dimitri...who then says that Sly must have some serious "fuzzy dice" trying to break into a prison. Think about that for a moment.
Also worth Mentioning is the Giant Carmelita fight in the Australia level. You probably thought, oh we just got to shoot the evil mask off of her, right? Nope, you have to climb up her clothes to whack it off. This of course leads to Sly getting very close to some seriously huge tracts of land.
In the final operation, you have to distract guards as Carmelita by belly-dancing for them, Sly' makes several pervy comments on this. The kicker? You have to shake the contoller/the Vita to shake her ass. Before that Murray really wanted to wear the outfit instead.
Hell, the first level with the Geisha's, just to let you know, in ancient Japan Geisha were prostitutes!!!!
Actually they weren't. They were entertainers who trained in singing, songs, and dances and performed for guests along with basically flirting with guests to make them feel special while also serving them food and drinks (Plus Geisha literally means "art doer"). Prostitutes were characterized by bright clothing and a bow in the front for easy access.
Plus, when Murray's in disguise as a geisha, El Jefe grabs his ass with a lecherous look on his face.
Also according to the story El Jefe knew about the Cooper Gang's plan of ruining his operation and when he saw Murray in the Geisha outfit he did not flip out or anything. That means he knew of Madame Geisha's imposter was Murray the entire time but didn't mind. (Think of that what you will.)
Madame Geisha's real name? Miso Horny. She's a rhino, but we all know that's just for plausible deniability.
Also, in a game where defeated enemies usually disappear in a puff of smoke, it's a little shocking to see Toothpick accidentally shoot and kill one of his guards. They probably only got away with it because we don't see the actual bullet wound or any blood.
While escaping from a Wild West Prison, Toothpick threatens to cut off Sly's thumbs....and his pinky. This would have been perfectly innocent if it had been written in the plural form...
Related to the finale of the Arabian level, where Le Paradox takes Carmelita hostage. At one point, when threatening to throw Carmelita off the blimp if Sly tries anything funny, he runs his hands greedily along her body, then pushes her over when she chews him out. The last we see of her is being helpless and tied up at Le Paradox's mercy...and then, later, when Sly comes to rescue her, she's back in her regular clothing. What did Le Paradox DO to her...?!