Nothing Is Scarier. The pun that nothing is more scary than someone jumping out, and that this technique is the scariest one.
Darth Wiki, fits the Vader/Anakin character. Darth Wiki is place part to have fun in and Vader is one of the coolest characters, but Darth Wiki is also a place for whining and Anakin is full of wangst in eyes of many fans.
The trope title Aerith and Bob is meant to invoke the Alice and Bob page, but also matches with the long-standing (but ultimately false) Final Fantasy VII rumor that Aerith's name was supposed to be "Alice," and the name makes even more sense.
Everyone Is Jesus in Purgatory can be misread as "If you're in purgatory then you're Jesus." However, it's making fun of people reading too far into things, ultimately leading to them saying, "Everyone is Jesus, also they're in Purgatory."
The meaning of the words "Sequel Hook": The question mark looks like a hook.
How long did it take you to realize that there's a reason the TV Tropes logo has a lampshade hung on it?
When people refer to a "scoop" of Eye Scream, it's a pun on the term "a scoop of ice cream," and makes further sense since the character gets their eyes scooped out.
Many people think that in scifi/fantasy, the common Bizarre Sexual Dimorphism where the female of a race looks like a Cute Monster Girl and the male most definitely looks monstrous/unhuman ismeant to appeal to male fans. It makes sense, right? But if you think about it wouldn't that also mean that even the manliest human would look a lot like a female of their own species to an alien male? Cue the fanfics...
Mining Accident On Troy is a Stealth Pun - combining Mole Miner (the trope of a character, like a mole, who mines) and The Mole's (Villainous spy pretending to be an ally to the heroes) background - so naturally it would be a mining accident.
In How Not to Write a TLP Draft, there were potholes for Your Trope. You might have clicked on it expecting to see some humorous lecture about how tropes belong to everyone, but the page is empty. There is literally no such thing as Your Trope.
The trope name Mind Screw is a Bowdlerised version of the phrase Mind Fuck.
On the page for E.T. the Extra-Terrestrial, someone changed Chekhov's Gun to Chekhov's Walkie-Talkie. This is a reference to the special edition where the guns were changed to walkie-talkies. note This would normally have been a casualty of the policy change banning potholed trope names, but it was retained as part of a note.
Another good example, that's slightly less old, would be Sailor Moon fans from the nineties gave way to pretty much the same reaction as we're getting now the whole "these guys are a pile of happy cigarettes" from the haters and a "it's the turning point of masculinity" from the fans side.
At first, that makes no sense, "a happy pile of cigarettes" who calls anyone that? Well, if you go by the correct definitions of many slang terms, "gay, faggot, fag," gay means happy, faggot usually means a pile of sticks but can technically mean a pile of anything, and fag means cigarette, so what's really being said is, "faggot gay fag," which is what bronies get called a lot of the time. Whoever that editor is, s/he's a genius.
In the older versions of Overly Long Gag, the page image shows up repeatedly inside the folders. This is not a technical glitch; rather, it's a sneaky joke that makes the page a Self-Demonstrating Article.
The images in Sugar Wiki's and Darth Wiki's home pages are opposites: a dark character turned sweet, and a sweet character turned dark.
Louis Cypher is usually a trope that unsubtlty hints that someone is the Devil or a demon and can be a little silly. But it actually makes sense theologically. Satan is above all guilty of pride, so of course he can't resist putting in a reference to himself even when he's supposed to be incognito.