This is pretty much the driving force of the "Prank War" between Streeter Seidell and Amir Blumenfeld of collegehumor.com. The "pranks" started out as relatively harmless - Streeter replaced the audio on a song Amir was listing to with audio from a sextape, and Amir set Streeter up on a fake date with a fake girl. But things changed with the third prank, where Amir submitted an embarrassing audition tape to a fake company for a network pilot that Streeter then played for the office, and it became an unwritten rule that the pranks had to be public. Amir pranked Streeter by convincing an audience at Upright Citizens Brigade not to laugh at any of his jokes, and Streeter responded by setting Amir up in a fake sketch with Human Giant, wherein they would insult his acting and eventually remove him from the sketch. Once he found out, Amir took it fairly well, but when he was informed that the sketch itself was not real and they had flown to LA for nothing, he was almost driven to tears, and things got personal. The next prank was the infamous Yankee Stadium prank, in which Amir arranged for a fake Jumbo Tron proposal from Streeter to his girlfriend Sharon. She accepted, but when he told her he didn't set it up, she slapped him, and they apparently broke up. While the pranks, admittedly haven't been that severe since then, they're still pretty bad: Streeter convinced Amir that he won a half million dollars with a rigged half-court basketball shot, and Amir convinced Streeter that he was going to die when he went skydiving and the parachute wouldn't open. It remains to be seen whether things will get worse from here, or if the War is over.
Monty Oum's videos, including Haloid and the Dead Fantasy series: How many different video game characters can we stick in this Crisis Crossover? How insanely over-the-top can the fights get? What gigantic building will the fighters destroy next? And most importantly, how much Fanservice can he stick in there?
And now that he works on Red vs. Blue, how much more epic can the next fight scene be? How much crazier will Tex's methods of punching people in the face get? How many more times will Grif get hit in the balls? How many different ways can we screw up Church's life this week?
BriTANick sketches. Each sketch generally starting off somewhere normal and increasing in absurdity until reality pretty much collapses. This sketch distills the concept into two people talking - Brian wants to know what a particular line from Twelfth Night is, and Nick's incorrect answers go from 'wrong part of the play' to 'wrong play' to 'wrong author' to 'frying pan' all the way up to quoting a section of a suicide note penned by Brian's dead ex-girlfriend.
Epic Meal Time boils down to this trope applied to food. To wit: their early endeavour of putting five different kinds of bird meat in a pig, and a few episodes later they broke the 100,000-calorie barrier.
The That Guy with the Glasses aniversary specials have basically tried to top each other every year. The first was just a short 20 minute brawl in a random Chicago building and the draw was that most of the contributers (And AVGN and Kyle Justin) all flew to Chicago to be in the same room at the same time. The 2nd Kickassia, was about an hour or so, had a decent plot and was set in more than one location and had multiple costumes, but was still fairly cheaply done mostly focused on the Critic, and was basically a Shaggy Dog Story in that nothing really changed. The 3rd Suburban Knights was a longer slightly more epic tale, with a slightly bigger cast with 2 ongoing plots, and some drama and consequences that lasted in the following year and leading into the 4th film To Boldly Flee an over 3 hour long epic tale with multiple story arcs, even more site regulars appearing, it's own original musical number, impressive film level special effects, and ending with several characters killed off and the universe of TGWTG changing forever. Notably its been mentioned that following annivesary specials will NOT attempt to top To Boldly Flee (at least not anytime soon), and will be closer to the earlier specials in terms of complexity.
In Worm, the antagonists that Taylor, our protagonist, faces go from bullies at her school to local gang leaders to city-killing monstrosities ... and worse.
Barbie: Life in the Dreamhouse has a very outlandish second season compared to the first. The cartoon went from showing Barbie go to the beach, attend parties, and redecorate her house to showing Barbie get trapped in her giant closet, become even smaller than doll-sized, and pursue dolphins that escaped into the sewer.
The Impossible Man: First chapter we are introduced to The Impossible Man teleporting himself without understanding it, by the end of the book, we see how his power truly works without understanding it.