Cartoon within cartoons:
Li’l Abner loved to read Fearless Fosdick
Jump Start character Frank Cobb refers to favorite cartoon Klondike Ike, but it’s never seen
Self aware cartoons:
Pearls Before Swine uses artist Stephan Pastis as a running character drawing that day’s strip
The Doozies by Tom Gammill often comments on the making of the strip
I know there are more …??
Walt Kelly’s POGO once had one of the characters (owl, maybe? I don’t remember) give a tour of the panels, pointing to the careful lettering and the artist’s signature, and commenting on the sloppy lines between the panels. That’s about as involuted as it gets, I’d say.
Did Kelly actually do that? I know the MAD parody did (“Gopo Gossum,” Mad #23).
Frank Cho represents himself as a chimpanzee in his strip “Liberty Meadows.”
There was an April Fool’s gag a few years back where comic artists swapped comics for the day.
For Drabble, it looked pretty much the same, but worse. The drawing was all scratchy and scribbly. Drabble asked his dad about the comics in the day’s newspaper and wondered what an artist would do if he was so lame no one would want to swap with him. The dad replied “I don’t know, draw the comic with his left hand or something.”
Yes, he did; that particular day he signed the strip “O’Tempora O’Mores”. I think it might be in one of the few Fantagraphics reprint volumes I have in my possession but I’m too lazy to look it up.
Once in Bloom County, Lola Granola was lamenting to Opus about her stupid name. She challenged him to come up with one that sounded dumber.
Opus replied, “Berkeley Breathed.” Lola said, “Well, all right. Name two.”
The strip was in Ten Ever-loving Blue-eyed Years with Pogo
If you actually mean “cartoons,” the classic is Duck Amuck
In comic strips, the artist in Overboard often appears in the strip.
In comic books, there are Ambush Bug and She-Hulk, both whom knew they were comic book characters. Ambush Bug had an encyclopedic knowledge of comics. There also was Herbie the Fat Fury, but I think he actually had real comic books (though obscure ones).
The post-Walt Kelly Pogo had a strip within the strip poking fun at modern “Dark Knight”-style heroes and villains. It ran about six Sundays, and was a hoot, managing to poke fun at involuted plotting and skewed panels and comic stand-bys like Alternate Universes…
which was a compilation of the first ten years of the strips, so the original ran in the papers sometime in the 1950s. I thought it had run in the Star in 1948-1949 but it’s not in that Fantagraphics volume; isn’t in either of the other ones I have. Ah, to get my hands on my mom’s collection of original TPBs right about now…
That SDMB favorite, Family Circus, is occasionally drawn by one of its characters (Billy, who has been 6 years for almost 50 years).
Doonesbury has had the characters stopping the story line to go to the reader mailbag, give (joke) previews of upcoming storylines, etc.
Zippy the Pinhead has done it forever.
Peanuts did it once, on January 1, 1974, when Charles Schulz was the grand marshal of the Rose Bowl Parade.
Lio did the best one I’ve ever seen. Some of Lio’s giant ants escaped, and attacked characters in a bunch of other strips. Except in The Lockhorns, where the husband’s only reaction to answering the door to a giant ant was “Loretta, your mother’s here.”
There’s several Fox Trot’s where the gag is “If Jason drew Hagar the Horrible” or some other comic. I know they did a week’s worth at least once and I’m thinking they’ve recycled the gag since then.
This messed with my head when I was a kid: Oor Wullie reads The Beano and The Dandy, but he also knows The Broons.
TV rather than syndicated, but one of the running gags on The Simpsons is that they’re “actors” starring in “The Simpson’s Show”.
My favorite web comic Jack had an arc featuring this. A damned soul insisted that fate was preordained and so he wasn’t responsible for his sins, and demanded an audience with Satan himself. When he finally gets to the very bottom of Hell, he finds that Satan is the author of the web comic Jack, who has been drawing everything that’s been happening. One of the spookiest moments is when the character says “if my life is a comic, then who’s been reading…” and then he looks out towards the “fourth wall” in frozen horror.
I think Bloom County broke the fourth wall more than once.
That’s what I was coming here to post. There was a follow-up, in which Elmer is the cartoonist drawing Bugs, but it’s not nearly as funny.
I remember many of the UK comics I read in the 70s and 80s (Buster, Whoopee, Whizzer and Chips, Topper, etc) would have a self-awareness to their comic book nature. It seemed natural to me, because it happened so often.
Breaking the fourth wall was the simplest form it took, when half the characters regularly spoke to “the reader” as they went about their adventures.
But occasionally a particularly surreal artist/writer would have his characters start to interfere with the panels, talk to the artist, or invade somebody else’s strip.
Cartoonist Bud Grace occasionally inserts himself into his Piranha Club strip.
Did She-Hulk only do this during the “Sensational She-Hulk” run?
Certainly during that period Jennifer was aware of being a comics character and the comics code, and regularly broke the fourth wall – such as being stuck in traffic and getting the “camera” to cut away to a sub-plot so that when it cut back she could be at her destination. I also recall her “literally” tearing holes between cells (comic cells) in order to move to a different location. Comics code / censorship awareness also came up – getting her clothes blown off but covered in tape with “censored” on it and the like.
Tony Millionaire regularly appears in Maakies.