Sick Sad World from Daria. I'd love that show
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Dhalgren?
I seem to remember one of the GTA games (maybe San Andreas?) had a stand up set from I think Ricky Gervais as something that would play on the TVs.
King's Misery when there are several bits from the novel the writer is making to please his capturer seems like a classic at this point. More classic is the trope of Necronomicon-alikes in lovecraftian stories. But I prefer The Book of Mindfulness that a character from the Black Book sitcom accidentially swallowed and became a saint, even god-like figure.
The Mr. Frog show in Smiling Friends.
The girl who looked up is a story told within Brandon Sanderson's Stormlight Archive series. It's told very well, and actually told twice.
There are other stories told to different characters in times of need, but I liked that one the most.
Gotta love The Rise and Fall of Sanctuary Moon from The Murderbot Diaries.
Black Mirror. News tickers and headlines discuss other world-building stories from different episodes.
Los Dias Y Las Noches de Monsignor Martinez in King of the Hill.
Who Dat Ninja
I'm surprised no one has mentioned the fake old movie that plays in Home Alone. "I'm gonna give you till the count of 10 to get your ugly yeller no good keester off my property before I pump your guts full of lead! One... Two... Ten!" 🔫🔫🔫🔫🔫
Angels with Dirty Souls
Image my disappointment upon becoming old enough to rent R-rated movies and finding out the only one I wanted was fictional.
Ballfondlers from Rick and Morty
Impotent Rage from GTA V
The Silver Shroud from Fallout 4
Sweet Bro and Hella Jeff
Sweet Bro and Hella Jeff from Homestuck. Although it actually predates Homestuck and was retroactively converted into media-within-media, does that still count?
Steel samurai from the ace attorney series.
This is not exactly what you're asking for (media inside media), but it's really close in spirit (nested narratives), and I really like it: a book written in Portuguese in the XIX century, called Noite na Taverna (Night in the Tavern).
The book has an overarching story of friends telling each other stories in a tavern, over booze; with all those nested stories being about love, despair, and death (it has a strong gothic vibe).
And, as each character tells the others a story, there's always that fishy smell that the story might be actually bullshit; and other characters do raise some doubts about its in-universe veracity (like Bertram does to Solfieri). And you, as the reader, do the same - but in no moment you question the veracity of the overarching story, and you feel like you're inside the tavern alongside the drunkards.
So it's a lot like the author is toying with your suspension of disbelief - redirecting it from the overarching story to the nested stories, and as you doubt the later you get even more immersed into the former.
If I must use an example of media within media, then my choice would be "The Book" within Orwell's 1984. I think that it's a great piece because it shows Orwell's views on politics and society, while still serving narrative and worldbuilding purpose - for Winston it's a material proof of the Inner Party's bullshit, for O'Brien it's a tool of the Inner Party to sniff out dissidence. (Note: 1984 is extremely misrepresented nowadays, I'm aware, but I still like it.)
Homer’s Odyssey.
Most modern adaptations present the stories Odysseus tells while visiting the Phaeacians as if they were the actual plot—but Homer’s audience would have known Odysseus as a notorious liar and trickster and wouldn’t necessarily have regarded his stories as true even within the context of the frame narrative. Homer’s epic focuses as much on the parallel stories of Telemachus and Penelope—I read the underlying story as their struggle to untangle Odysseus from his own web of deceptions and fantasies and bring him back to reality.
Ow! My balls! from Idiocracy
There's been some stuff coming out lately that makes me think this show isn't far off.
It was a clear send-up of "America's Funniest Home Videos" at the time.
Check out https://nestflix.fun/ for a Netflix-like way to browse popular fictional media like this
The movie Twins starring Danny Divito and Arnold Schwarzenegger plays at the drive in the anime Blood Blockade Battlefront
Inside the 90s anime Martian Successor Nadesico, there is a 70s-era anime called Gekiganger III. Characters various levels of knowledgeable about, or fans of, the show. A single OVA episode was released in addition to the clips from within Nadesico.
Mysterious Mysteries of Strange Mystery from Invader Zim
Come to Zim!
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Nation's Pride, in Inglourious Basterds. "Who wants to send a message to Germany?!" ~Fredrick Zoller
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"I'd buy that for a dollar." in RoboCop.
Wormhole X-Treme! from Stargate SG-1
In-universe, creating that show was a genius move, if anything legit leaked they can just say it's some fan fiction from the show and not from the real Stargate program.
Makes you wonder what the Stargate show was hiding :P
Station Eleven from… Station Eleven is probably there only one that’s been as interesting to me as the story itself, I guess because it’s such a big part of the story and character motivations. The book and show are both good in their own ways, but I particularly like the passage repeated throughout the show:
I remember damage, then escape
Then adrift in a stranger’s galaxy for a long time
But I’m safe now
I found it again, my home
This may not fit perfectly into the that category but i think it's cool how Lazarus Jones exists in the media in some capacity in most of the GTA games. One of the best threads of continuity throughout the series.
The "I'd buy that for a dollar!" guy from Robocop.
The Princess Bride is one of my favorite examples of this, especially because the "story within the story" is the main story, which is unusual.
The book House of Leaves is presented as a documentary within a book within a book. Really fun read, too
Just saw "The Play That Goes Wrong," and it is a two hour masterpiece of a play within a play.
I see videos of complete productions on youtube. Go watch one.
For something similar Noises Off is a hilarious movie about pretty much the same thing.
I just stated watching The Goes Wrong Show on Amazon. Not sure if I would appreciate more than 1 episode a night, but the first one had me laughing so hard I couldn't breathe.