Hilarious in Hindsight/My Little Pony

General

 * During an interview at a MLP convention back in 2008, Bonnie Zacherle, the creator of MLP, stated that she originally envisioned the MLP franchise as gender neutral, in other words something aimed at both girls and boys. It was other people at Hasbro who decided that the toys should be marketed exclusively to girls (which, among other things, meant amping up the amount of ponies with pink and purple colors). During the interview, Bonnie remarks that nevertheless there were definitely many boys who enjoyed the toys, and that she "felt bad" that the franchise came to be marketed exclusively to girls because "why shouldn't boys play with ponies too?". Flash forward to 2010 when a certain MLP-reboot is released that is specifically designed to appeal to both genders, and which indeed manages to attract an absolutely enormous amount of male fans. Bonnie must be happy!
 * One of the G1 ponies was named Princess Serena. Also, Sandy Duncan was famous for playing the title character in the 1979 Broadway revival of Peter Pan. In 1984, she voiced flying pony Firefly.
 * Do you know of this series now? Well try watching Fantasia..or just The first part of Pastoral Symphony. Or just look at the comments.

My Little Pony: The Movie
"You need to find a home;

How about the Astrodome?"

My Little Pony and Friends

 * Alright, take Nightshade. He's a Michael Jackson Expy. He's white and he shouts, "It wasn't my fault" when getting into trouble for doing bad things to children.
 * Moondreamers featured a big cat named Ursa Major, something that would eventually find its way back into My Little Pony-related media 23 years later in My Little Pony Friendship Is Magic.

My Little Pony G 3

 * After My Little Pony Friendship Is Magic brought completely redesigned Rainbow Dash, the line in the Core 7 opening which says "Rainbow Dash always dresses in style" sounds pretty ironic, and of course it went through Memetic Mutation, as seen here.
 * Another one involving Rainbow Dash. She didn't believe in "flying ponies" (pegasi) in Friends Are Never Far Away, but come the next generation and she's a Pegasus.
 * In G3.5's Twinkle Wish Adventure, a Blooper gives Cheerilee googly eyes for about a second. This was almost an entire year before Derpy Hooves.

My Little Pony Friendship Is Magic
"Lauren Faust: My favorite kind of guy!!!!! Wish there were more guys like you..."
 * The best example has to this. Back in 2008 Lauren Faust posted a poll on her Deviant ART page asking if any of her followers were My Little Pony fans. At the time it wasn't announced that she was involved in a reboot and one of her comments says she has a "very specific reason" on why she's asking her fans about Ponies. One fan, a male at that, says he likes cute ponies and isn't afraid to admit to it. Lauren had this to say.

"I’ll never forget when Anna Wintour called me to play at this event, she called me and said, "I would like you to play at the Met gala, but I just want to make sure, because I’ve seen you perform before, that you won’t be swearing during the performance." So Anna, I will do my f#@&ing best!"
 * Twilight Sparkle was named before... well.
 * One of the common complaints about Twilight Sparkle's toy was that it had replaced Spike with an owl. Come the plot of "Owl's Well That Ends Well", however....
 * When Photo Finish made her début, nearly everyone compared her appearance to Lady Gaga. Her demeanor, however, is an homage to Anna Wintour, editor for Vogue Magazine. What makes this hilarious in hindsight? This statement from Lady Gaga, which has a minor Take That to Wintour:


 * Pinkie Pie's comment in the pilot about quiet parties being boring seems like a throw-away comment; fast-forward to the Grand Galloping Gala, and Pinkie's first excitement of the event is quickly dashed when she finds its exactly the kind of quiet, stuffy party she lambasted.
 * Also from the pilot, Twilight Sparkle's mane and tail turn into fire thanks to drinking hot sauce. Fast forward to the high point of "Feeling Pinkie Keen"...
 * "Rainbow Dash always dresses in style!" While this is true for the G3 Rainbow Dash, this is completely contrary to the tomboyish one of this show. This is because the Friendship is Magic Rainbow Dash is simply Firefly, an equally energetic pegasus who loved to fly, with Rainbow Dash's colors.
 * But then there's that preppy outfit she wore in May The Best Pet Win... And the gala dress Rarity made for her.
 * The garish outfit Fashion Style Rainbow Dash ships with. Dresses in Style indeed.
 * In "Sonic Rainboom", one of the pegasus bullies tells Rainbow Dash that she should get herself some wings like Rarity's. Almost six months later, the first image of the Glimmer Wings Rainbow Dash toy was leaked.
 * Before the show, a "pink pony" was (and still is, admittedly) associated with trippy hallucinations, a crazy person, or a Non Sequitur Thud from someone who is just knocked out. Then in prances Pinkie Pie...
 * In "The Cutie Mark Chronicles", Rarity finds a big rock and is underwhelmed by it. In the next season...
 * This Real Trailer, Fake Movie, which was actually inspired by the Transformers and G.I. Joe movies, and predates FiM by about a year.
 * In August 2011, a fanfic called Writer's Block was released that revolved around Twilight Sparkle having trouble coming up with a friendship lesson to send to Princess Celestia. Then came the season 2 episode "Lesson Zero"...
 * Similarly, one fanfic submitted for Equestria Daily's "April Foal's" contest was "Big Dragon", in which Spike grows humongous overnight, gives in to his draconic hoarding instincts, and engages in a King Kong homage with Rarity in the Fay Wray role. This was published about eight months before "Secret of My Excess", in which...well, yeah.
 * The fanfic Fluttersertive was written well before "Putting Your Hoof Down" was announced, but both roughly revolve around Fluttershy causing trouble and becoming a Jerkass after taking some assertiveness training too far.
 * Someone ponified Q and Picard well before Discord was revealed.
 * Fan-favorite background pony Carrot Top has a pretty epic scene in "Over a Barrel" where she jumps out of a building and kicks buffalo ass like an action movie star. In the Blind Bag toyline, she (or a pony with a similar appearance) was given the name Golden Harvest. It's fitting if you think about it.
 * Speaking of the official toys, the Riding Along with Rainbow Dash toy was released well before the first airing of "May the Best Pet Win!" (Word of God says that "May The Best Pet Win!" was conceived and written almost a year before it aired, and the toy was first revealed at around the same time, so there may or may not be a connection here.)
 * One fan made a custom Lyra Heartstrings toy by repainting a Twilight Sparkle toy, almost three months before Lyra's first official toy was first glimpsed.
 * At the end of "Lesson Zero", Spike tries to add a postscript to the Mane Six's joint letter to Celestia that he didn't need to learn the lesson of the day. At the end of "The Super Speedy Cider Squeezy 6000", Applejack actually does send a letter to Celestia stating that she didn't need to learn anything from the events of that episode.
 * Cadance, foreshadowed by Pink Hasbro Celestia.
 * In the first episode an exasperated Twilight Sparkle remarked: "All the ponies in this town are CRAZY!" Throughout the rest of the season, each of the mane cast (including Twilight herself) had a breakdown. It only got funnier when Twilight had an even bigger breakdown in "Lesson Zero".
 * In "The Cutie Pox", Apple Bloom nicknames a hula hoop move "The Hoopla", 9 years after a memetic scene from SpongeBob SquarePants.

Hilarious In Hindsight moments from other works because of My Little Pony:

Fan Works

 * Fallout Equestria is a Friendship is Magic fan-fic set after My Little Pony's equivalent of a nuclear war, written before season 2. Fast forward to this scene in Lesson Zero...
 * Also predicted Pink Cloud, a character named Pipsqueak/Little Pip, and Canterlot's city shield. A Running Gag on the fanfic's comment threads was, "Season 2 is still FO:E Compliant!".

Film

 * The first Transformers film features a small cameo from Pinkie Pie (a little girl is holding a G3 Pinkie Pie plushie) as a nod to Hasbro owning both franchises. Suddenly this commercial makes a bit more sense.
 * Disney's Tangled came out little more than a month after the première of My Little Pony Friendship Is Magic. Now try to think of the sun-themed kingdom, the heroine's snarky reptilian sidekick, the fact that the royal army's got a horse as the one competent member, and most of all the fact that one of the Snuggly Duckling thugs collects ceramic unicorns (which happen to be same in color scheme to Twilight Sparkle) and not chuckle.
 * The coat-of-arms for the sun kingdom is, by coincidence, identical to Celestia's Cutie Mark.
 * Remember the infamous Wingboner from My Little Pony Friendship Is Magic? It looks like it happened a lot earlier.

Literature

 * From Guards Guards by Terry Pratchett: "They felt, in fact, thoroughly bucked up, which was likely how Lady Sybil would have put it and definitely several letters of the alphabet shy of how they normally felt." Cue "buck" being used as a common Unusual Euphemism by FIM's Periphary Demographic.

Live Action TV

 * While Kamen Rider Fourze merely took a more Hot-Blooded approach to The Power of Friendship, even mirroring the "love and tolerate" message at one point, "A Friend In Deed" seems to be taking the references in the opposite direction, with Pinkie Pie already being friends with everyone in Ponyville and Determinatoring her way to become Cranky's friend. Then we see Cranky caught without his wig and putting dirt on his head, much like Tomoko. The most telling indication is at the end, when Pinkie takes off like a rocket.
 * Turns out "Ponyville Confidential" shares its premise with part of Fourze #25-26 (the gossip column).
 * Friendship is Magic Bitch, a fanmade animation where Princess Celestia frequently utters the phrase, "You ain't findin' no bananas... ON THE MOOOOOOOOOOOOOOOOOOONNNNNNNNNNNNAAAAHHHH!!!!!!" becomes much funnier when you watch this All That sketch from 1997 (skip to about 2:06 in, the line itself is about 4:00 in).
 * "Apple's rubbish, I hate apples." says the Doctor to a little girl in "The Eleventh Hour", which aired in April of 2010. Fast forward to "Call of the Cutie" where a certain background pony gets terrified of a little girl trying to sell him some apples...

Magazines

 * During the early days of Nintendo Power, the Player's Pulse section once featured a topic of the issue being the most infuriating gaming moments for players. One such player ranted about something involving his sister, and ended his post with "God must be a girl!" Three decades later...

Newspaper Comics

 * An April 2010 story arc of Doonesbury beginning here that heavily involved a Captain Ersatz of Pinkie Pie, considering the facts that Doonesbury is a very serious strip, and a mere 6 months afterwards, Friendship Is Magic premiered.
 * In one issue of My Cage, Norm tried to make something girls and boys would be interested in by making "Cute Force", made of several overly butch versions of popular girl's toys from The Eighties. One is "My Little War Horse", showing a little pony in robotic military gear. Fast-forward to 2011 and the Brony movement...
 * A FoxTrot comic from the 2000s had Jason playing with Paige's Barbie doll as "Indiana Barbie" so he could do things like crush it with the garage door, crush it with a large ball, and feed it to "The Iguana Of Doom" (Quincy). This predicted Daring Do quite well.

Stand Up Comedy

 * Stephen Colbert made a shout-out to bronies. He made a pony joke back in 2009, confusing G3 Scootaloo for Pinkie Pie.

Web Animation

 * In the Homestar Runner cartoon "Commandos in The Classroom'', the Cheat Commandos are settling to watch "Pony Fights 2" at the beginning of the cartoon. Who would have thought manly grown men watching ponies would eventually become a reality?

Web Comics

 * In the comment section of the final part of the webcomic Ensign Sue Must Die! a user sarcasticly comments: "My Little Pony, eh? Now THAT'S a fan demographic waiting to happen..." in response to  The comment is made 1 month before the premiere of a certain animated show.
 * "For Pony!" was used as a battlecry by Richard of Looking for Group fame...years and years before Friendship is Magic was even conceived.

Web Original

 * In The Nostalgia Critic's review of A Troll in Central Park, the NC lists several cutesy and girly franchises that he says are butch compared to the movie. One of these franchises is My Little Pony which was in G3 when this episode was released. Then Friendship is Magic was released, with gained a large male Periphery Demographic.
 * Another My Little Pony: Friendship is Magic example: In his review of IT, Critic commented on the abundance of balloons and asked when one would look intimidating. Well, Critic, Discord did just that....
 * During The Nostalgia Chick's My Little Pony review, Nella tells us the tales of her own ponies, including that of the kindly schoolteacher with a heart of gold that all the children loved even though she was sometimes a whore. Flash forward to the My Little Pony Friendship Is Magic episode "Call of the Cutie", the schoolteacher introduced in that episode, and the photo of the way she dressed back in the day.
 * While this is more Hilarious in Hindsight in a Black Comedy sort of way, it's hard not to at least chuckle when watching this video (original video is going to be deleteted sometime in the near future) if one read the infamous My Little Pony Friendship Is Magic Dark Fic Cupcakes beforehand.
 * In the Abridged Series Friendship Is Witchcraft, Pinkie Pie is represented as secretly being a gypsy witch. In the My Little Pony Friendship Is Magic episode "It's About Time", Pinkie Pie dresses up as a gypsy when trying to see Twilight Sparkle's future. Also, Twilight has a brother, Rainbow Dash has to dash, and robots do exist in some capacity.
 * This anti-Twilight picture from 2009, which predates the Twilight Sparkle character itself.

Western Animation

 * The mere existence of "bronies" makes this scene from the pilot for Fosters Home for Imaginary Friends where Terrence gets threatened by a bunch of pastel-colored male unicorns even funnier. "Youse thinks we're goily, huh?!"
 * Even funnier is that Lauren Faust worked on that show as well
 * Even more hilarious when you find out who voiced Terrence.
 * Way back in 2001, there was a little series that ran on PBS called Dragon Tales. In it, we have Emmy and Cassie, girl and dragon. Emmy would ride Cassie one an episode. Now, fast forward to 2010. Fluttershy was revealed to be afraid of dragons, except Spike because he's so tiny. Emmy = Andrea Libman = Fluttershy. Also, Cassie happens to be the youngest dragon in the dragon main characters group.
 * In 2006, American Greetings relaunched its Care Bears line, featuring a new bear named Oopsy. He doesn't really have a belly badge yet, and he's silly as heck, and clumsy to the point of always crashing into things. Fast forward four years. His voice actor was called onboard to voiced a pair of ponies. How does this two relate?
 * Try not to snicker when you consider the Garfield and Friends episode "Wade, You're Afraid" is about a flightless coward trying to overcome his cowardliness, and involves a bull.
 * The Grim Adventures of Billy and Mandy episode "The Schlubs" opens with Grim watching Billy's My Troubled Pony DVDs and actually enjoying it. That episode first aired five years before Friendship is Magic
 * On October 9, 2010, a season 2 episode of The Penguins of Madagascar had this scene that was intended as a joke about Private being...odd. ONE DAY LATER...
 * In a 2000 episode of The Simpsons, Milhouse is revealed to have an old My Little Pony blanket. To make things funnier, a contributor to the Simpsons Archive episode capsule commented that the toys "were babyish for Milhouse" and "marketed to little girls to boot." Ten years later...