At the end of the tutorial level, the mysterious voice guiding Alan spouts a random phrase and asks if Alan understands, only to ignore him when he says no. The last time he shows up, he tells Alan that he "will let you have your dream back now." It's the delivery that makes it hilarious.
If you listen to the radio interview when you first get to the cabin, the waitress from the diner will excitedly spill the beans on who the "famous artist" is. Alan's groan is hilarious.
During the TV interview we see Alan do via Flashback, the other guest on the show is Remedy's Sam Lake. Lake, the original actor for Max Payne, is asked if he could "Do the face!". He replies by making a constipated expression.
Alan: I lifted the page in front of my eyes and read it. In it, I lifted the page in front of my eyes and read it. In it...
Finding Barry Wheeler wrapped in Christmas lights.
"For protection. Like garlic against vampires!"
And the headlamp, don't forget the headlamp:
Alan: Hey. I want a headlamp!
Barry: Sorry Al, last one.
Barry referring to his hard hat as his "flaming eye of Mordor". It's funnier in the strategy guide, where Alan and Sheriff Breaker cringe after he says it.
Alan and Barry getting drunk off the Andersons' moonshine and drunkenly spouting nonsense about being able to write ten books a year and becoming booze millionaires, respectively. Overlaps with Crowning Moment of Heartwarming when Alan breaks down about Alice and Barry pats his head.
Alan: If I wanted to, I could write ten books a year. And they'd be the best books that year!
Barry: No you couldn't.
Alan: That's right, I couldn't. But I could. 'Cause I'm a writer!
Barry's Night Springs joke:
"When someone throws a damn school bus at your head, and you're about to take a ride with someone who may or may not have a pilot's license, you're cleared for departure... to Night Springs!"
When Alan exits a building at the Anderson farm, a Taken farmer springs out yelling "Stay away from my daughter!"
Barry imitating Alan with the cardboard cutout.
In fact, the cutout in general, because you can just tell that Alan loathes it and it follows him everywhere.
Watch what happens to the parade float after it goes past you. The Dark Presence can parallel-park like a boss.
The achievement description after you beat the first elite Taken.
Nordic Walking: Unlike Stucky, you enjoy incontestable health benefits. Namely, you're not dead.
The description before unlocking it is just as great.
Take a walk through the logging area, meet one of the quirky locals.
Most of Barry, really. He was written as the comic relief, and he comes through like a king.
Even Imaginary Barry, who turns into an antagonist:
It's great that you first make yourself an imaginary friend, and then you can't even get along with that guy! People skills, Al! You're a master.
The fluctuating Taken voice only enhances the delivery.
Pretty much everything said by the Anderson brothers, ever. It's like a nonstop parade of hilarity - especially once they go nuts on the lodge and trap the staff in the staffroom.
One of the patients in Cauldron Lake Lodge is a slightly crazy video game developer. One of his rants starts about nightmares, but somehow turns into something about mullets.
"...but it wasn't supposed to be about mullets, and now it's about mullets, and when it's in slow motion, they call it 'Mullet Time' because..."
Emma Sloan offering Alan a "herbal detox suppository."
From American Nightmare:
Emma: So... you might have brain damage, you're about to go to great things with a magic piece of paper, and you came here from another dimension?
Alan: No, I'm from New York. I was just visiting another dimension.
Emma:Oh, yeah, okay. My bad.
The achievement for collecting all the manuscript pages in American Nightmare is called "One Day I'll Buy a Stapler".
Mr. Scratch's Super Effective Sales Trailer. Basically he goes on a killing spree at Remedy Entertainment's offices, Squees over all the good reviews he's gotten, and then enslaves the game's lead writer (and a potted plant) so he can force them to write more games about him. He spends the entire trailer as a hammyattention grabbing bastard. It's the large amount of dark humor that makes this great.
To make things better, Sam Lake responds to the demand to write by limply slapping the keyboard and falling unconscious/dead. The potted plant promptly falls over with a comedic timing that no plant should have.
"I just wish these things would stop blatantly violating the laws of physics inside my observatory, it's just rude!"
When you complete an arcade stage, sometimes the narrator might put on a deeper voice and say, "Because you won, I am speaking in a dramatic voice."
Some of the moments in Scratch's videos qualify. In the Barry recording, after spending the whole game talking about the horrible things he's planning to do to the people Alan loves, and the nightmare inducing actions he's done against the people in Night Springs, he declares that he'll keep Barry alive....so he can fire him.