Anti-Climax: After months of waiting for a new episode after 69's cliffhanger, and then fans having to get the DVD to see it, who's the Hummel Figurine? Melvin. That's it. And Ask That Guy just takes questions like normal straight after.
Ass Pull: His death of being asked if he wants to ask a question and then blowing up, with Chester being the one to tell the audience he's not coming back. Plenty of people have blown up in the CA universe, but for some reason this one sticks.
Big Lipped Alligator Moment: In episode 63, That Guy is hit with a giant wooden hammer from off-screen. When he attempts to answer the next question, he's hit with it again.
The entire YardOz segment, which is a parody of Zardoz featuring a giant floating head in the sky that tries to convince That Guy to engage in self mutilation for no apparent reason, is ignored, and then the episode goes on without a single reference to what the hell just happened. At least it explains how he got a new pipe.
"I'm going to be a monkey now".
Cargo Envy: People have gone on record saying they'd love to be that pipe.
Crosses the Line Twice: Pretty much 'every single word that comes out of his mouth. It's impossible to find a single episode that does not include something that would make the show ban worthy in some countries.
And yet somehow, he managed to be even more horrifyingly indecent by inviting Sage to answer questions.
Example: For his ninth video, he casually greeted his viewers:
Fanon: The gloriously nutty fanfic fandom has decided that the porn movie "Bunny Does Dallas" involved a man in a bunny suit raping a Bound and Gagged Critic with a carrot.
Fridge Horror: He interacts far more with his creator (non-verbally anyway) than Critic ever did. If he ever gets through the fourth wall, then Doug is really not to going to have a good time.
His voice getting more effected. He was rapidly losing the cool he once had, to tried to compensate by using a tone that went well beyond reasonable poshness ages ago.
Fridge Logic: How on earth did he manage to get into heaven? Twice?
Justified by God Is Evil, since apparently Ask That Guy has been considered appropriate to be an evangelist.
"Funny Aneurysm" Moment: In episode 31, he made a joke about all the scary freaks of nature who now know who he is. Let's just say Doug's fanbase has got much creepier since then.
If Doug's marriage ever ends, regardless of if by divorce or death, then episode 54 will appear this way. Hopefully, though, this won't happen for a very very long time.
Growing the Beard: Episode 4 was when his sadism and issues really started to appear. Before that, he was just a suave-but-wacky moron who answered every question wrong.
A lot of people think the beard grew again in episode 53 when he moved locations, as there was more focus on Villainous Breakdowns, interactions with other people and giving him extra Hidden Depths.
Harsher in Hindsight: In an early episode he has a breakdown about dying alone and forgotten because he's so intelligent, but then snaps back to claim he was just joking. Fast forward to the finale and he does indeed die alone.
From the forty-fifth episode, the praise to Blip is, at the least, irritating now. The site has had many issues with paying various producers, the infamous cullings of producers, and, finally, it's closure on August 20th.
In 4.6, Ask That Guy collapses from a heart attack, and Chester is upset saying “he's dead forever”. In the finale, Ask That Guy dies permanently, and Chester doesn't care.
In 15, he rants that if he was a figment of someone else's imagination, wouldn't a good rational person with a conscience get rid of such evil like him. In late 2014, he is indeed got rid of, though not for decency purposes as it was just to announce the site name changing.
Hilarious in Hindsight: In episode 27, he says people only watch his show for soft porn. About twenty episodes later, well, just have a look at the fanservice entry.
In episode 59, he makes a typical “Justin Bieber is a girl” joke, gets lauded and gives a Take That to the internet; “Thank you for so needlessly hating a little boy whose music you don't have to listen to!" A couple of years later, Doug got a lot of heat for a transphobic sexist joke about Orlando Bloom and Bieber being women catfighting. So the character ends up nicer than the actor.
I Knew It: His parents were badly abusive. Cue the gasps of surprise from absolutely nobody.
Jerkass Woobie: Occasionally, when he realizes how sick and twisted he is and gets upset.
His Sanity Slippage in the last ten episodes drove home the idea that there really is a pathetic little boy underneath all that monstrousness.
LGBT Fanbase: Far more sexual and fetishizing than the casual Everyone Is Bi style of Demo Reel, but still one of the most popular shows for it thanks to Doug's willingness to fellate anything phallic he can find. The fact that Doug said his only rule for the show was to never punch down, only mock hate and not spread it, helped a lot as well.
Most Annoying Sound: "THIS IS THE MOST ANNOYING SONG IN THE WORLD!" It sounds funny the first few times it plays, but when he makes that song the background music for the whole episode, you will want to stab your eardrums with an icepick by the time the credits roll. Which is kind of the point.
Never Live It Down: While he'd probably see it as a positive, the most shared gif of his show is the giving fellatio to his pipe.
Nightmare Fuel: In episode 63, when asked if he ever attempted a world record, he says "I'm the only person in the world that can do this" and then he turns into a floating brain with ominous demonic sounds play while he screams in terror.
In a DVD episode, the murder of the camera-man. It's from his POV and we can hear him begging as Ask That Guy first shoots him, and when he's out of bullets, kneels down with a big smile and snaps his neck. Fact that camera man is probably played by Rob doesn't help.
Sage's episode, with screaming in ATG's face and making him whimper, and the I Have You Now, My Pretty moment of feeling him up (while ATG tries to shrink away as much as possible) and telling him he's been good.
Squick: While thankfully offscreen, Sage at the end of his episode drags Ask That Guy off to demonstrate “eating piss and than having [Santa Claus] come on you”. Sage also added on later (in the defunct formspring) that he'd also stabbed ATG and fucked his stab wounds until he was bored.
They Wasted a Perfectly Good Character: In the second half of Ask That Guy's run, he had a cutely sadomasochistic canon-sleeping-together relationship with a narrator who became a character (of the Love Martyr kind) of his own. But in the finale, there's no reference to the relationship and ATG is oddly sexless.
Too Cool to Live: Not 'cool' in the badass sense, he had a lot of breakdowns towards the end, but a Depraved Bisexual with canon gay relationship with his narrator, deep psychological issues and has so done so many awful things he's close friends with the devil should have more than 71 episodes, a couple-of-years Series Hiatus, and an Ass Pull ending.
Viewers In Mourning: Very few fans of his actually liked his death. It's mostly because unlike Critic who got a love letter send-off, and even Donnie got to Rage Against the Author, Ask That Guy was just killed to change the site name and it showed. Adding insult to injury, Ask a Ninja got to be on the site months later, with the tagline "The series that inspired us to create Ask TGWTG is now on Channel Awesome!".
The Woobie: Pity the poor narrator. Although he's not completely without fault, he never says anything against the Ax-Crazy questions often given, or tries to stop Ask That Guy's killing sprees.
The GPS got proposed to, married, had her husband leave in a temper tantrum and then come back to shoot her all in one day.