ThisSluggy Freelance strip joked that a (fictional) wrongful hiring scandal had drastically hurt the strip's viewership. "Two people used to read Sluggy Freelance. Now only one does. In percentage terms, this is devastating for the comic."
In this strip of The Order of the Stick, one of the demon roaches says, "They'll let any old hack write a sourcebook these days" in reference to the strip's acid-breathing shark. The acidborn template, with the specific example of the acidborn shark, appears in the Dungeons & Dragons sourcebook Dungeonscape, co-written by OotS author Rich Burlew.
Which begs the question of whether Rich first dreamed up the acid-breathing shark for his webcomic, and included it in the sourcebook merely to lay the groundwork for his Take That Me...
Each print compilation of The Order of the Stick comics opens with a Foreword by one of the characters. Typically they spend the Foreword mocking the concept of the strip, the writing of the strip, the art style, and the reader's intellect for having wasted their money on an amateurish comic they could have read for free.
In Snips, Snails, and Dragon Tales, the Order is telling stories to one another. In Belkar's, the heroes die, which doesn't amuse the rest of the group:
Elan: Belkar, I can't think of a single story where the protagonist dies. Roy:Ahem. Elan: Well, at least, not any that are worth the paper they are printed on.
Something*Positive occasionally features Choo-Choo Bear "off-stage" to address the reader directly, declaring that his author is a lazy, talentless hack who can't get his act together.
Choo-Choo Bear: Alas, dear readers, you know when you see me Randy is planning something "special." It'll be over quickly, I promise ... And if you hate it, don't worry. It's not like this will be the project Mr. "I swear I'll update Midnight Macabre" will actually finish."
In another strip, Milholland gives a nod to the Fourth Wall when PeeJee asks, "Why does everything around here revolve around sex?" and Davan, who's reading a book, mutters, "Bad writing." When glanced at in curiosity, he says, "I'm reading a John Grisham book, worst writing I've ever seen." Milholland also draws filler strips with himself in them, usually self-deprecating in some way. This version of his Author Avatar even has a razor blade with hands and feet as his muse, who constantly says/does whatever he can think of to make Milholland miserable or want to kill himself.
And then there's this strip. Technically, Milholland did subvert a little of what the character predicted. A little.
Jayden and Crusaderembodied this trope for much of its early stages. Later the self-deprecation slackened a little, but it's still there.
ThisDominic Deegan strip has Mookie poking fun at his own inability to draw noticeably different faces.
Tom Siddell, the author of Gunnerkrigg Court. Not so much in the comic itself (Tom doesn't write himself into the comic and promises that he never will) but in talking with his fans: If you ask him about the art, he'll probably tell you that he thinks it's bad and that it used to be worse. If you ask him about the hollow-eyed cartoon self-portraits resembling male variant of Zimmy he uses as avatars, he'll tell you that they're more handsome than he is.
8-Bit Theater: there's lampshading the metric buttloads of Filler, and then there's his footnoted clarification of a point about "most consistent work you've ever seen online."
Terrible work is still consistent work.
Strip 1,000 was called "I canít believe someone was asshole enough to make 1,000 sprite comics." Strip 1,001 was called "I canít believe someone was asshole enough to make more than 1,000 sprite comics."
And then there's Hussie making fun of Vriska's Creator's Pet status by having his Author Avatar propose to her...only to get clocked in the face and turn up sobbing pathetically later on.
From the newsposts:
I will be attending ECCC in Seattle this weekend. If you would like to come see your favorite cartoonist ever, this could be your chance. And if you go there and find your favorite cartoonist is unavailable, you can always come see me instead. I will console you. This kind of humor is known by professionals as "self deprecation" and as you can see I'm quite good at it.
Even the fandom itself is frequently self-deprecating, to the extent that "Homestuck trash" is a common Fan Community Nickname. It's especially prevalent on Tumblr, where posts mocking Homestuck tend to get insane amounts of notes...which are largely from avid fans of the comic.
Fan: This fandom does so many things ironically, I can't tell if it's actual self-hate or irony. Actually let me rephrase that: I don't think anyone can tell if everyone hates Homestuck or if we're all just ironically reblogging Homestuck hate.
Living With Insanity has a few of these. One has to wonder if David Herbert really does think he's a talentless hack who lucked out with a great artist.
After reading his blog posts, it seems he really does. He praises his collaborators and insults himself often.
Ken: "Let's admit it, Kovalic's about as organized as a wet mound of marmots."
In the webcomic Jack, Artie Sullivan dislikes an author for being too gory when he's not being too preachy. The author is (who else?) David Hopkins.
LDS cartoonist Howard Tayler pokes fun of his own religion, with a joke about Mormons being teetotal in this strip from Schlock Mercenary. Early strips also contain jabs at the initial poor quality of the artwork.
Questionable Content creator Jeph Jacques introduced the character of Yelling Bird into the comic, whose sole purpose is to berate him when he is unable to get the comic up on time for various reasons. Yelling Bird doesn't stop there, though.
In this regular comic, Angus is reading Butts LOL: The Jeph Jacques Story.
A slightly more subtle version in Spinnerette. Protagonist Super Heroine Heather admits to hating manga style comics. Odd considering the general art style of the comic.
During chapter 58 of Welcome to the Convenience Store one character is showing off short (yet true) stories that have happened. At the end the manager says that the artist/writer was just being incredibly lazy.
In Sinfest, one character reads Sinfest. Criminy's anthropomorphic feminism book reacts badly. Also a regular staple for whenever the Author Avatar character shows up.
David Morgan-Mar, author of Irregular Webcomic!, periodically mocks his own drawing skills and penchant for awful, awful puns. He even once convinced Jane Goodall to pretend to slap him for how he portrayed her LEGO alter-ego. (Well, actually, he asked her to pretend to punch him - she convinced him a monkey-slap would be more in-character for her!)
Dragon Ball Multiverse: Raditz makes a comment about Dabura "being affected by such a simple technique." The technique in question: the Makankousappo.
Mark Shallow of Adventurers! took a potshot at his older artwork towards the end. In a flashback during a conversation between Khrima and Cody, he briefly reverted to the old art style. Then had Khrima insult it.
Khrima: Hey! My head was not that square, and I believe you had fingers.
Ozy and Millie creator Dana Simpson also does some songwriting. One strip had the lyrics to one of her songs appear, and Felicia mocked the heavy use of overly emotional metaphors.