You Don't Know Jack/Funny

And right this way, please.

All of the Impossible Questions in Volume 3 live up to their name, with the exception of one- its category is "It's a Dog!" and the question effectively amounts to "What has four legs and barks?" Guess what the answer is. Yep, a dog.
In one of the episodes in YDKJ 2011, the staff go on a picnic before finishing all the questions. The first six questions are normal, but they become more mangled as the remaining people rush to complete questions for the episode. It starts with a question with two of the same answer, to Donny writing a question, to Kim pointing out that the acids found in the tryptophan actually makes Sleepy less sleepy, to Cookie making up a question that is inspired by a snapple cap, and finally culminates in a Jack Attack round where all you have to do for a match is pick whatever the phrase tells you to pick, all while Cookie frantically tries to get the game shut down.
- In Donny's question there's not only Cookie's reactions to it, but also the responses you get when you answer wrong.

Cookie: "Oh please, don't be so knave." Yeah. Right. Right Donny! We wouldn't want anyone to be knave, would we?!

The opening sequences for Volume 2 are pretty damn funny. For example, if you opt for a single player game;

Cookie: Oh, so you're playing with yourself tonight?

Offscreen Voice: Cookie, please.

The Parody Commercial for "Sunshine Suppositories" from The Ride. Starting with a man named Johnson getting chewed out by a boss, things quickly get derailed when the boss says, "I'm not here to blow sunshine up your ass!" followed by a cheery, "But I am!" Mickey Mousing to indicate an Ass Shove or two later, and, well, smiles all around. And then, the tagline: "Spread your cheeks for a little sunshine today!"
A question asks for the correct pronunciation of the singer of "Smooth Operator." It's shar-day (close enough). The next question (all category choices lead to the same one) is about the Marquis de Sade, leading to the host's comment, "He was probably ticked about being called the Marquis de Shar-day."
One of the questions from 2011 which asks which of the following is not a Crayola crayon color eating another crayon color. Among the choices is "a beaver eating macaroni and cheese." Picking it will cause Cookie to thank you for giving him an excuse to talk about the image of a beaver eating macaroni and cheese. After the question is over, no matter how you answered, Cookie will continue talking about that choice.
All of Cookie's dreams from Nocturnal Admissions.
Question 8 of episode 5 from JACK PACK 1 in 2011 opens with Cookie dedicating the question to his old high school chemistry teacher. Then starts the question off with "Suppose a chemistry teacher died a painful and horrible death and went to Hell..."
On episode 25 from 2011, Cookie had planned a party and sent invites to the staff prior to the show. However, throughout the episode the staff each made several excuses on why they couldn't attend ranging from a colonoscopy to a two-for-one deal lobodomies, finally boiling down in question 10 when Cookie realizes the entire staff are "sick". He then makes the question based around which of the four lies he heard makes any medical sense with Cookie not only peppering in more insults toward who made the excuses in the first place in addition to pointing out why they're wrong, but calling everyone out even on the right answer.

Cookie: An otolaryngologist is an ear, nose and throat doctor. All the rest of you are *BLEEP*ing bad liars.

The commercial for Brannigar and The Hawk, a buddy cop movie starring a loose cannon cop portrayed by Sylvester Stallone and his equally loose cannon partner portrayed by Stephen Hawking.