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, Rose 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 (pictured above). 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.
Alan: Bastard.
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.
While Breaker, Wheeler, and Wake are moving through the town, the Dark Presence possesses a Deerfest vehicle to send after you, and after hitting or trying to hit you, it then pulls up and parks the damn thing next to a few other cars.
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 Heartwarming Moments 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 tells Barry to go to the Anderson farm instead of leaving Bright Falls, Barry has this to say:
Barry: When this is through, if we make it, I'm done with darkness. You're going to buy me a tanning bed as a gift and I'm gonna live in it!
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.
A subtle one, but near the beginning of The Signal, a phone appears which is clearly a Verizon phone. Zane calls, and the first thing he says is a perfect shout out to the classic Verizon commercials.
Thomas Zane: Can you hear me? Can you hear me now?
A funny Taken line:
"CHAINSAWS ARE NOISY!!!"
"OMEGA 3 FATTY ACIDS ARE GOOD FOR YOUR HEART!"
"IT'S RABBIT SEASON!"
"FISHING CAN BE A HOBBY AND A JOB!"
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.
During the tour of the lodge, at some point squeaky noises can be heard. Go around the corner and one sees Tor hit a board game with a colorful toy hammer aggressively.
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..."
Barry tries to convince Alan that he might be going crazy, because of all his talk about a Dark Presence. Once the Dark Presence goes after Barry and he complains about it on his cellphone, Alan shoots back that Barry should just relax because Alan's just going crazy.
Barry's "Night Springs" phone calls at the beginning of chapter 5. The funniest is when you stick around to the end: in spite of the urgency of the situation, Barry can't let himself interrupt a chatty person to tell them the code word.
In chapter 2, during the bird attack, Barry is thankful that, in this horrible situation, at least he's not allergic to birds. And then he sneezes.
At one point, there existed a pirated copy of the game. It played the game entirely fine, with no real copy protection to speak of, except Alan is wearing a silly eye patch for the duration of the game.
Alan Wake's American Nightmare
Emma offering Alan a "herbal detox suppository."
One of Alan's and Emma's conversations:
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 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.
Placeholder: super effective sales text goes here (so people buy it)
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.
Mr. Scratch: Yeeeep.
While under the influence of the Dark Presence, Serena gets her horniness dial turned up to eleven and basically throws herself at Alan. His response upon approaching her building during the second time loop boils down to, "Ugh, here we go..."
You can check the names of the movies playing at the drive-in. During the first loop Alan will notice Samurai vs Conquistador 2 is playing; apparently he hated the first one and is annoyed they made a sequel while he was in the Dark Place.
" is pure Nightmare Retardant: two women go into a basement, and discover a wormhole. Then a man appears in the basement, himself not sure what the deal with the wormhole is, with it being heavily implied that he's the writer of the episode, suffering from writer's block.