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Even after the credits roll and he survives trying to betray you, he's funny. When you call him, he says, "Hey. I'm bleeding. You okay?" Nothing Personal indeed.
During his first job as your supporting sniper he recognizes one of the bad guys and tries to remember his name. When that doesn't work he just pops him. Then we get this. He then remembers that his name was Douglas and he had the best rabbi jokes.
Also: "Oh...you're using yourself as bait! Oh my God, I love it because it's such a horrible idea!"
Seeing a bad guys footnote as being "Killed a dolphin". Even better, you can hack his phone to distract him. By playing a repeating dolphin call!
One of the calls you can hack into has people discussing who's an Assassin and a Templar. Oddly enough, 2 out of 3 of the Three Stooges are Assassins and one's a Templar.
One of the CTZNOs videos you find while hacking core servers shows a middle-aged man indulging in some public indecency from his high-rise window. The software attempts to analyze his gyrations, comparing them to a few yoga poses, several dance moves, and other things before flashing up UNIDENTIFIED just as the clip ends.
One that's funny in a dark way is a window washer going about his job when some guy plummets right past him, screaming the whole way down. The window washer just stands there in a stunned silence.
Made funnier in a blink-and-you'll-miss-it way is the software's attempts to identify the guy plummeting past, its first guess being Bird, then Plane, then Terrorist.
Another had a boy playing Assassin's Creed with his father watching. He apparently just successfully assassinated someone and everyone who's ever played AC knows that the Asshole Victim is now confessing everything. We get this exchange.
Dad: Why is he doing that? Kid: He's an assassin, Dad. Dad: But why is he talking to the guy...he just killed? Kid: It's a confession? Dad:Well, that's just dumb. Kid: Dad, please. You're ruining it.
During one side mission, you can hack a gang member's grenade to explode. His dawning reaction to the beeping - realizing it's coming from his own grenade and what is about to happen - is comedy gold.
Really, many people's reactions when you hack their grenade to explode.
(paraphrased) "What the fuck! This ain't Afghanistan! I ain't the Taliban! I-" BOOM.
(also paraphrased) "Tell my wife- Tell her I've been fucking her sister!"
After you take down Defalt, Aiden asks if he had anything else, T-Bone mentions he had a USB sticks with 6 gigabytes of lesbian porn and Aiden says that T-Bone can keep it.
Some of the Engineers audio logs are amusing. They're pretty much a prank war between Blume employees all around the Bunker.
Some of the Privacy Invasions can lead to some hilarity, such as a topless woman playing Russian roulette with a guy who really gets off on it.
A not-so-funny one, but still funny in its own way, is a single mom leaning against a counter, and you can hear her kids arguing in the other room. She goes absolutely BALLISTIC and sounds like she's about ten seconds away from killing them both as she screams that she's going to send them to the middle of nowhere so they can appreciate just how good they have it before sending them to their rooms without any dinner. All while restraining herself from outright swearing at them.
Another is of a woman acting flirty with the plumber, who returns in kind. It's dialogue straight out of a porn film. In an added bit of hilarity, both people are ex-Olympic athletes, for whatever reason. For all you know, you may have stumbled on an actual porn film shoot.
If you profile them, they both have the same last name. It's likely you're meant to think it's a married couple doing some erotic roleplay.
Yet another involves a man and a woman in a apartment together, with the player's view starting off behind them. It seems at first to be a real Tear Jerker, with the man urgently, lovingly telling the woman that she needs to eat and that she wasn't sure how she would react to being rescued from an abusive relationship. But then you access a camera pointed in front of them and discover that the "woman" is in fact a storefront mannequin reported stolen from a department store.
Pressing and holding the "hack" button causes Aiden to whip out his phone. However, some sicko found that if the key/button was pressed repeatedly, Aiden would perform an action that resembles... well... see for yourself. Bonus points of hilarity for the fact that Aiden just so happens to be wearing a trenchcoat.
If you get on a motorcycle and move at ridiculously slow speeds, citizens will still leap out of your way like it's a frantic high speed chase. Poor driving in general can result in this.
During one of the human trafficking missions:
Carl Breenwood: What are you going to do, hmm? Cry? You're a useless TIT! Do you think if I show the court the giant file I have on just how big a useless tit you are that they won't applaud me?...Are you CRYING?! What's that fucking snorting sound? You're a disgusting. Useless. TIT!
Angry Joe: (Halfway between being Squicked out, and just plain horrified) Daaaaaamn, Carl Breenwood, you're a fucking asshole, dude!
In the Bad Blood DLC, during T-Bone's escape from the ctOS building in the opening mission you run into a surprise guard. Though actually — he's even more surprised to see you.
Guard: Oh my God, it's Ray Kenney!
T-Bone: Five bucks for an autograph, asshole! (proceeds to either shoot or take down the guard)
A minor one where Adrian is using Social Engineering to track down a target. Call Target niece about her uncle. Hang up. "Wait for it" She then calls her uncle about how someone is trying to use her to get to him.