Deadpan Snarker/Web Animation

"Simmons: Well of course it sounds stupid when you say it like that."
 * Foamy the Squirrel provides the page image.
 * About half the cast of Red vs. Blue, especially Grif and Church.

"Roamin: Gary, why are we even friends?
 * With the Exceptions of Caboose, Donut, and Sister
 * Lampshaded when the Reds ask Grif to come up with his own plan and he's unable to think of anything. "My skills lie more in listening to other people's plans and telling them what's wrong with them."
 * The Director judging by the letters we hear dictated in Reconstruction has a pretty sharp pen. When explaining what 'The Meta' is to the politician who's new oversight he resents he describes it as "Merely an entity trying to increase its power, in my view this isn't a rare occurrence at the moment." Ouch.
 * And then in Season 9, there's Pilot Four-Seven-Niner, whose razor-sharp wit puts Church, Tucker, and Grif all to shame.
 * Gary to Roamin the Paladin in Unforgotten Realms. Usually in the form of blunt, tactless explanations of how Roamin is being stupid.

Gary: Well, no-one will be friends with you, and I enjoy pissing on people's parades.

Roamin: Better reasons than most, I suppose.

Gary: Not really, it's probably the worst reason for being friends out of anyone who has ever used the word "friendship" to describe their bond with another person."

""Were on our way to Candy Mountain, Charlie!" "Yeah, that's great."
 * Homestar Runner: Strong Bad. Strong Sad sometimes fulfills this role when he isn't busy being The Eeyore.
 * Raimi Matthews from Broken Saints.
 * A lot of characters in TTA fall into this category, but Kirbopher15 is by far the worst offender. It gets worse when he goes into 1111 form and is openly acknowledged as being an asshole in said form.
 * Charlie the Unicorn. Charlie is the worst offender.

"I think I died long ago, and you two are my eternal punishment.""