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From Episode 8: Someone asks what is the meaning of life, and the answer is given... from the dictionary.
Ask That Guy With The Glasses episode 16. Four words: "I will find you."
In Ask That Guy episode 17, he answers his first question with a long, drawn-out, irrelevant statement. Then he apologizes, saying he's wasted everyone's time, and puts up a link to another video which he says will more than make up for the time he's just wasted. Its a Rickroll. Then, his second question? "How do I spot a Rickroll?" And his answer is an evil smile, and a very certain "You can't."
Ask That Guy Episode 25. The question is: "Why is lemon juice artificially flavored, and dishwashing liquid made with real lemons?"
"Because I'm Batman."
[Quick flash of That Guy wearing a Batman mask]
When That Guy With The Glasses is asked the question "Can this question be any more obvious?" his response is "It sure can! Watch!" (cue the question in giant letters with exploding fireworks in the background)OBVIOUS, OBVIOUS, OBVIOUS! THIS QUESTION IS SO OBVIOUS! IT IS OBVIOUS AND BEAUTIFUL. SPAM IS YOUR FRIEND! CANADIANS DO NOT WANT TO EAT YOU! OBVIOUS! "Too subtle? Fuck you."
READ THE BIBLE! Read the Bible every day, all the answers are in there! Or, if you don't want to read the Bible, read the Chronicles of Narnia! It's pretty much the same book!
His ending his response to a question in the same episode by saying something is as 'dead as the Dead Sea', and his stunned reaction to then getting a question asking 'How dead is the Dead Sea?' is priceless.
His reaction to the question "Wanna cookie?" is just hilarious.
Ask That Guy: (Enthusiastically) DO I EVER!? (Crashes into the camera and falls over)
Scores even better due to the Refuge in Audacity factor: to film that segment, Doug actually walked around his neighborhood in a bathrobe while holding a very real looking gun in plain view, with a Joker-like Slasher Smile on his face.
His reaction to a woman asking him about why men are disgusted only when women brag about their large genitalia and commenting on her own.
(horrified stare) I'm not touching that one with a ten foot pole.
Someone asks Ask That Guy why no one can understand the adults in the Charlie Brown cartoons. That Guy's response? Answer the question in the "Waugh, waugh, waugh." sound-effect style from said cartoons.
"YOU WILL PERISH IN FLAMES, ALL HAIL SATAN LORD OF DARKNESS LOL !!!!!"
The first question of the 40th video, namely why a nickel, worth five cents, is larger than a dime, worth ten cents.
That's a very good question. * Cut to next question*
In the 41st video, we learn the most cruel torture That Guy has ever witnessed. Twilight "Never again."
In the first Christmas Special, he's asked what his true love gave him for the Twelve Days of Christmas. He says, ""I'll tell you..." music swells, ATG takes off his Santa hat, puts on a top hat, picks up a cane, and says, "...nothing! That craven bitch."
Kwanzaa. That is all.
"How many pricks could one prick prick if one prick could prick pricks?.
Episode 44: After That Guy warns Bennett that he does things disturbingly, Bennett proceeds to spend the entire video utterly traumatizing That Guy.
Bennett the Sage: ...and then [your mother] will know the nadir of your pain! (Smash cut to Sage directly in front of the camera) Bennett the Sage: PAIN! (A deeply disturbed Ask That Guy looks over Sage's shoulder)
Even The Narrator, who normally reads the questions without reacting to That Guy's replies (except when the script calls for it) is clearly having difficulty getting through the questions, thanks to Sage's increasingly dark and disturbing answers. The content of the questions clearly doesn't help matters.
Then in Episode 46, there's a rather disturbing question, and all That Guy can do is look very scared and ask "SAGE? Is that you?"
That Guy taking a short break between questions to contemplate reindeer sex.
Just think about all the things you can do with those antlers.... in fact, I will.
The 3rd Christmas Special has That Guy tell us that Hummel figurines are the works of the devil. Cue one talking in a deep demon voice while Dies Irae from Mozart's Requiem plays.
Episode 18, wherein he encourages a questioner to take drugs despite the setbacks.
I do drugs all the time and it has had absolutely no side effects whatsoevJESUSHELPME!
From Episode 5, after That Guy dies from a screamer-related heart attack, Chester A. Bum takes over. His answers to the other questions and how he reacted when he heard the narrator was hilarious.
Chester: "AAAH! Who are you?"
Narrator: "I'm the narrator, you idiot."
Also, when Chester looks for money on That Guy's corpse in the end of the episode:
Ask That Guy: Let's say that this pipe is Kermit the Frog and that this hole is Miss Piggy; I'll demonstrate for you- *cut to picture of adorable puppies* OH MY GOD THAT'S SO HORRIBLE! THAT'S THE MOST HORRIBLE THING I'VE EVEN SEEN IN MY LIIIIIIIIIIFFFFEEE!!!!!
"I bet you'll never eat pork the same way again. Or vaginas! With onions. (winks)
Episode 50: Upon being asked "Why do you close your eyes when we make love?" That Guy gets into rather nasty argument with the voiceover. Upon leaving, all you hear are the plaintive sobs of the voiceover...to which That Guy returns and apologizes tearfully. Then he says "Let's fuck," to which the voiceover reminds him they have a show to finish.
And once the show is finished, the voiceover brings up the proposition again. This time, That Guy accepts.
Episode 52: "Oh, Hej. As in the... Danish hej, not the ''American' hey." (bites his thumb at us, sir)
Episode 53: "Pardon me sir, but would you have any Grey Poupon?"
Ask That Guy: You have made a powerful enemy today, son. [puts pipe into mouth]
Episode 54: That Guy gets engaged to his GPS and announces it to thunderous applause from the Aninite '10 convention hall. Three hours later, the two split up, only to reconcile as "best friends"...then That Guy shoots her. Doubly hilarious when you realise the GPS is voiced by Doug's real life fiancée.
The ending. Also: "Oh hey, Benzaie."
*Holds his pipe up to his nose* "I'm an elephant!"
The Devil talking over part of Ask That Guy's segment.
The Devil: Hey guys. The Devil here. Um, I'm talking over this part because uh... Yeah, uh, even this part's a little too much for me. And uh... you really shouldn't hear it. It'll... it'll give you nightmares, man. I know I'm the Devil, I should be, like, all about that, but, um... no, this is... this is really fucked up. Yeah, uh, trust me. You lucked out here, folks. You... you really lucked out.
"Why does food never look as good as it does on the picture?" With him answering because it is covered in fairy semen. And finishing with, "unless, of course, you don't believe in fairies, in which case DIIIIIIIIIIIIIE!!!!!!!!"
(Over-the-top dancing and lip syncing to Queen's Bohemian Rhapsody, incorporating the wild spraying about of Windex and that clip of Doug quitting his former job. Ends with the display of That Guy's iconic pipe, which had been broken.)
Even funnier: two questions earlier, someone had asked "Easy come, easy go, will you let me go?" and Ask That Guy had responded in a completely straightforward way and didn't seem to get the reference.
Question: My girlfriend is into erotic stories, and she sometimes hints that she wants to re-enact some of her favorites with me. However, I broke into her "Erotic Stories" file, and found that they all end in the castration of the male involved. Should I been concerned?
After the "answer" to one question flashes on screen much too quickly to read it, Ask That Guy's next words are, "How dare you pause and read that! I'll see you in Hell!" Even better, when you do pause and read it, here's what it says:
Really? You went back to read this knowing it would send you straight to Hell? What the Ass-Puke is wrong with you? It's friggin' Hell! Fire, pain, the Devil, it's worth that just to find out what this said? That Guy with the Glasses was actually kidding when he said you were going to Hell, but now that you've actually come back to pause it, we have no choice. You're going to Lem. It's a place like Hell only ten times worse. It's not written about in the Bible because every time someone tried writing about it, they'd cut their own head off. It's that bad. So I hope it was worth it, I hope it was worth pausing the video for that. See ya in Lem ya miserable piece of donkey rectum. En-friggin'-joy!
"Cum in the Clam. Buns of Cum. Ass Full of Grass. Hamster Master. Flick the Dick. Grilled Cheese Feces. Nun Buns. Captain Picklesauce. Penis and Venus. Sock Puppets 12. Penis Butter. Animal Anus. Pigs in a Blanket. Sex Mix. Honey Cum. Easter Bunny Does Dallas. Whore Shoes. Skull-Fucker. Cannibals are Cute. Cock-A-Doodle. Nose Plunge. Sodomy Jonas. Lobotomy Sodomy. Famous Anus. Plug-A-Butt. Choke-A-Hoe. Amber Fields of Gay. Pork-Buster. Slabs of Abs. Lickin' Lincoln. Titty Titty Bang Bang. Mucus for Lucas. I Want to Have Sex With this Woman and then Film It Because People will want to Pay Money to See It. And The Passion. But hey, I'm just starting out!"
Narrator: Now that Apple has created an iphone app that can anwer questions with voice command, is there any point to your existance anymore?
"Should I put rims on my wheelchair's wheels to look sexier for my girlfriend?" "Oh yes indeed. But you know what would be even sexier? Walking."
Doug even apologizes for this one after the credits.
From Episode 67:
His Too Dumb to Live moment: Namely, since blood is red and so is wine, surely they must be one and the same, so he cuts himself open when he wants a drink. He takes the resultant wooziness as proof of his hypothesis, up to and including the fact that he's getting rather woozy now....*faints*.