Namely, it's when Not the Fall That Kills You meets Overly-Long Gag; a character takes a fall (perhaps from an Absurd Altitude), and falls for a really, really long time, long enough for either the character or the audience to start wondering when the fall will end. Generally unrealistic (unless someone is sky diving), especially since the character will almost always survive the fall. It's rather hard for it not to be Played for Laughs. It might involve a Bottomless Pit, or at least a near-bottomless one. Bonus Points if the character becomes bored and starts to look for things to do to pass the time, though it can be equally hilarious to just have them scream their lungs out the entire time (perhaps even stopping to take a breath mid-scream, which is a sure indicator that this trope is in effect).
Just a little bit of trivia: it would, theoretically, actually take you 42 minutes (so less than an hour) to fall through a frictionless hole drilled through the Earth and accelerating only due to gravity. Considering that the earth is about 6,000km thick, there's little chance you'll fall for more than a few minutes from any part of the atmosphere with breathable air. Unless you purposefully slow your descent.
Compare Not the Fall That Kills You, the common result of falling for hours, and Gravity Is a Harsh Mistress.
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Anime and Manga
The trap-door pit in Ilpalazzo's headquarters in Excel♥Saga is subject to this gag at one point. There's plenty of amusing background scenery during the fall.
Usually it's a fairly short fall, ending in a splash. However, the first time, Excel spends a good two minutes lamenting her fate, and later we see Il Palazzo hired Puchus to expand it. He eventually uses it to drop Excel from Japan to America.
In the finale of Sailor Moon SuperS Chibi-Moon is thrown from an asteroid that is rising up to the moon and falls down to earth, down to Tokyo, with Sailor Moon after her, in a sequence that takes about four minutes within the show.
Kite, otherwise a rather serious OVA, has one of these that doubles as an Overly-Long Gag. Sawa fights a man in a bathroom; the two end up falling out of a large hole in the wall. Sawa grabs onto a sign which snaps off the hinges. Sawa and the man spend about two minutes falling, during which they see a random couple having sex in an office. They hit a tunnel and go through the roof; they hit a car and go through the floor of the tunnel. Another two minutes of falling. The car, the mook and Sawa hit the ground and go through to the subway system, upon which they hit a subway train. The sign then falls the rest of the way and blasts Sawa into a nearby building.
Kevin Matchstick is suspended over a bottomless pit while being interrogated by the Umbra Sprite in The Hero Discovered. In a horrific variant of this trope, the Umbra Sprite describes a cat he tossed down the pit whose cries he could hear echoing back up for weeks.
At one point in the Tales of Suspense story "The New Iron Man Meets The Angel," Iron Man's jets fail during an aerial battle with a Brainwashed and Crazy Angel. While Iron Man exclaims at least twice that he will hit the ground in "seconds," his fall lasts for more than one page of the magazine. During that time, Iron Man reflects on at least two regrets (not coming up with suitable Famous Last Words and never saying goodbye to Pepper Potts and Happy Hogan) and the Angel pulls a Heel-Face Turn, before the Angel finally saves Shellhead about 16 panels after letting him fall.
In a Spongebob Squarepants comic, Spongebob and Patrick drop down a seemingly bottomless pit. They fall for so long that they grow beards and then shave them off before hitting the ground.
Though it was actually an illusion; they were being held up by a fan.
A variation on this was done in Undercover Brother, where the titular hero was first being led to the BROTHERHOOD headquarters, the entrance was through a barbershop. Then the seats drop, and we see Undercover Brother and Sistah Girl falling for quite a while, with UB screaming all the time. Then it turns out they only dropped a single story with the fans and some clever lighting providing the falling effect.
Even in the book Gandalf later on claims to have been falling forever, but in the movie version of Lord of the Rings: The Two Towers we actually see Gandalf and the Balrog falling down the pit under the Bridge of Khazad-Dûm, taking several minutes to reach the bottom, and fighting each other all the way down.
In Twice Upon a Time, Flora falls for so long after stepping out of Rod Rescueman's flying bachelor pad, Rod has enough time to wash and iron one of his dirty capes before flying to her rescue... sorta.
In "Bill and Ted's Bogus Journey", the two title characters find themselves in this situation when they are exorcised by Missy and her new age friends. After several minutes of screaming, Bill remarks, "Dude. This is a totally deep hole." and Ted replies "Yeah...now what?" and they start screaming again because there is nothing else they can do. The drop last so long and B&T are so bored that they end up playing 'Twenty Questions' before FINALLY hitting the bottom (Hell).
In The Hitchhiker's Guide to the Galaxy, the Infinite Improbability drive changes a missile into a sperm whale two miles above the surface of a planet. It has about half a page of monologue to come to terms with its own existence, comprehend its situation, and come up with a name for the big round thing rushing up at it really fast before it learns, rather abruptly, that the ground does not wish to be friends with it, whereupon it becomes a rather messy canyon at ground zero.
In the Robin McKinley novel The Hero and the Crown, the protagonist climbs an insanely huge staircase, and then falls down it when during her battle with the Big Bad, it's destroyed. The kicker is that it's way, way more than hours. Based on the state of her injuries and the landscape she landed in, she spent somewhere between one and five centuries climbing, and six to twelve months falling.
In The Wheel of Time while Skimming, one of the Aiel being transported falls off the platform everyone's on. The area in question is essentially an endless nothingness where one will fall forever without chance of rescue. Gulp.
This is how they eventually deal with the Gholam. It's lured into leaping through a portal with no platform on the other side.
In the Tunnels series, if you fall into the Pore, you fall for days. What eventually stops you is not any sort of bottom, but the gradual loss of gravity. (The Tunnels series has a rather strained relationship with inertia... don't think about it too hard).
In House of Leaves, Navidson is stuck at the bottom of the Grand Staircase after it suddenly gets a lot longer, and hears a coin drop. He realizes it must have been dropped by Tom right after the Staircase stopped expanding, over fifty minutes ago. The book explicitly notes that this makes the shaft of the Staircase longer than the diameter of the Earth. Considering how fucked-up the geometry of the house is, it makes perfect sense.
Used in some Choose Your Own Adventure books. One has the main protagonist fall into a bottomless pit (one is a dragon, and the current speed prevents the dragon from opening the wings), and another has the lead charcters fall down a bright, cold, icy slide.
In Wizard, second novel in the Gaea Trilogy, a character falls from the hub of the gargantuan living space station all the way to the outer torus. Between the low gravity inside of Gaea and the sheer distance, it takes the better part of a hour, allowing sufficient time for a winged humanoid to notice her, and offer to slow her fall to a survivable speed in exchange for sexual favors.
The Abyss from His Dark Materials takes this to a ridiculous extreme — it's mentioned that someone who fell in would die of starvation long before they reached halfway, then they'd keep falling as a ghost even after this.
In Tik-Tok of Oz, the party falls down the Hollow Tube all the way to the other side of the world. The trip down takes over an hour; the return trip takes longer, but they are riding a dragon (who is in no hurry).
Live Action TV
One German comedy show had the reoccurring skit "The man who was falling down a very tall cliff". Which was about a man who was falling down a very tall cliff and each week met new interesting people or experienced suprising events.
The Lemon Demon song "I've Got Some Falling To Do" deals with a man who falls off an airplane and finds himself with enough time to get a phone call from Death, get bored, think of an interesting way for himself to die and ponder the nature of perpetual motion. In the end, he's caught and rescued by a giant squid... even though he would have rather just kept on falling.
One of the multi-strip story arcs in Calvin and Hobbes had Calvin holding onto a balloon only to have it float away with him, high into the sky. When it pops, he falls for incredibly long time. At one point he looks down and expects to wake up from a dream at any moment, but it doesn't happen. Luckily, he finds his transmogrification gun and "safes" himself (that is, turned himself into a safe).
Also, a Demetri Martin joke:
One time I was riding the escalator and I tripped. I fell down the stairs for an hour and a half.
-My friend once spent 72 hours falling off the top of a building.
-Surely he died?
-Of course! He was without food or water for three days.
Many of the Super Mario Bros. games feature levels in which Mario falls a long distance, and is able to steer himself through the air to grab rows of coins on his way down.
The very first part of Super Mario Bros. 2 has you falling from a door in the sky onto a hill in Subcon.
Super Mario Sunshine has a glitch involving Mario, Yoshi, and a flower that forcefully moves sand on the beach to send Mario flying past the sun. The resulting fall can take anywhere from 45 minutes to over an hour.
Easily doable in Glider PRO given a sufficient expanse of open sky.
Torin falls down one in the adventure game Torin's Passage, and he falls so long that he has to stop to catch his breath mid-scream.
The events of Persona 4 really kick off when Yuu (MC) and Yosuke go into the TV and fall all the way into another dimension.
Doable in most Grand Theft Auto games, provided that you use the invincibility cheatcode and have access to aircraft. And depending on where you land (e.g. the sea), sometimes doable without the aforementioned cheatcode.
In Portal, you can set up a portal loop such that your character falls indefinitely through the ceiling and into the floor. There's an achievement for doing this, called "Terminal Velocity" — you have to set up a portal loop and let yourself fall for about 15 minutes to get it.
GLaDOS: Well, since we aren't going anywhere — well, we are going somewhere, alarmingly fast actually, but since we aren't busy other than that...
The Curse of Monkey Island had a scene where Guybrush is falling and falling and falling until you remember that you picked up an umbrella at some point earlier. You have plenty of time to open your inventory and select it, allowing him to drift gently to the entrance of the cliff lair of some smugglers.
Banjo-Tooie features an elevator to move between the five floors of Grunty Industries, only there's no elevator and you have to climb a rope to get to the top. Without any elevator to get in your way, however, you can jump off from the top and fall for such a long time that Banjo's falling yell ends before you're even halfway to the bottom. The fall is so long that you will die even with full health (unless you have the fallproof cheat active).
In the first game, Labyrinth Zone Act 3 starts with a water slide that is a vertical Wrap Around, serving as one of these until the player attempts to break out of it and finds the switch allowing passage to the rest of the act.
This also happens near the beginning of Ice Cap Zone in Sonic 3 & Knuckles. How do you make it stop? Land on that ice block that's the only flat surface around, and it'll break off and crash through an otherwise-unbreakable wall.
Shadow the Hedgehog had Cosmic Fall. You spend the entire level jumping from falling platforms.
In the original Castlevania on the NES, the entrance to level 4 starts by Simon falling down a chasm into the level. It's not even close to endless, but some fans hypothesized that the fall causes severe wounds to Simon, explaining why he takes four units of damage from everything after that point.
In The Legend of Zelda: Majora's Mask, in Snowhead Temple, there's one area where you must fall for several in-game hours (if you aren't using the Inverted Song of Time, that is) as Deku Link — just to get the last Stray Fairy of the area. Of course, it's worth it to get the Double Magic Meter. All the while, Link's just making strange spasms while holding onto the flowers.
Any 3D Zelda game, when using a cheating device and a levitation code, can result in this.
Many stage fatalities in the Mortal Kombat series feature this, but the one most in effect of this trope is the Sky Temple in Deception (which returns in Armageddon), from which the fall is outrageously long.
Noob Saibot's Babality has baby Noob accidentally create a portal loop, which he falls through until the screen goes black.
Metroid Prime 3: Corruption has, in what has to be a Homage to The Lord of the Rings, Samus fighting Ridley in freefall early in the game. The shaft they're falling down is explicitly shown to be several kilometers deep. Samus survives because Rundas catches her before she hits bottom. Ridley survives because he's Ridley.
First, when Sabin and Cyan reach Baren Falls (and Shadow leaves) they jump over the edge to continue their trip. They fall alongside the cascade and fight carnivorous fish, including a miniboss, all the way down, taking a few minutes to do so.
Later, when trying to reach the Floating Continent via airship, they fight the Imperial Air Force boss in mid-fall. This is quite a lengthy encounter, with clouds scrolling up at high speeds the whole time, but when the party reaches solid ground they're no worse for wear.
Bayonetta has a few of these. The playable introductory sequence has you tumbling down a cliff while fighting angels for four minutes, and the penultimate boss battle has you falling continuously from a skyscraper for however long it takes you to defeat him. The final boss really takes it up to eleven though, when you punch the spirit of Jubileus out of her body and send it falling into the heart of the sun from beyond the orbit of Pluto.
God of War 3 has the sequence right before Cerberus, the game's That One Boss. Kratos Literally jumps off the Daedelus' Labyrinth and falls forever until he gets to the bottom of the chain. What's really strange, is how the impact from hitting things during the fall causes damage, yet the impact from reaching the ground does nothing.
During the prologue of the H-game Sumaga, the main character has enough time from waking up in freefall to think to himself for a bit, have an extended conversation with three flying girls, watch an aerial battle between said girls and what they mistook him for, and have one of them make a mad dive towards him before he hits the ground and dies. He's awfully calm about it, more so than having Laser-Guided Amnesia.
Team Fortress 2: the Scout and Spy have this reaction when falling into the bottomless pit in Ghost Fort (being a fast-paced action game, you will only fall for about four seconds before they say their appropriate voice lines, then die so you can respawn).
The First SPY Fox game puts this at the very beginning after being ejected out of a plane. Naturally, you use a spy gadget to break your fall.
The German internet phenomena Coldmirror has one sketch called "The NEW EIGHTH Harry Potter Book" in which she, dressed up as JKR, presents "Harry Potter and the bottomless black hole". She even reads an excerpt: "Harry looked at Ron and Hermione and fell and fell and fell and fell and fell and fell and fell and fellandfellandfellandfellandfellandfellandfellandfelland."
One of the Homestar Runner main pages shows Homestar falling through the air for an endless amount of time. By rolling over certain buttons, the viewer could also make Homestar stop in midair, fall even faster, or fall in the upward direction.
There was a Teen Girl Squad episode where So and So fell down a bottomless pit. It was commented that starvation would take her.
In one of the Teen Girl Squad cartoons, So-And-so falls into the school football team's "bottomless spirit pit". This prompts the observation that, "When you fall in a bottomless pit, you die of starvation." An Easter Egg at the end of the cartoon shows that So-and-So eventually gets bored of falling and turns to conversation with her imaginary boyfriend.
Explored and rejected in the What If? entry "Free Fall". Jumping off the tallest sheer cliff on Earth would result in only 26 seconds of falling time.
In an arc of a gaming webcomic, one of the PCs falls down a bottomless pit, which is made bottomless by having a teleport zone zap them up to the top of the pit repeatedly. It's said to kill you via the eventual build up of air friction burning you to death.
A chapter of Flipside has two characters going down on a seemingly endless staircase only to discover that the whole thing is just three floors and a pair of portals. A non canon intermission has one of them fall off. You can guess the rest.
The old The Legend of Zelda cartoon had an episode where Ganon was thrown down a Bottomless Pit by his rebelling minion, after he was trapped in an invulnerable sphere that could only be broken by the Triforce. He falls for quite a while, until the story eventually comes back to him when he realizes that his magic still works inside the sphere, and he conjures up a balloon to slowly float his way back out. Actual times or distances are never mentioned, though they are implied to be fairly ridiculous.
The early cartoon "Heckling Hare" had both Bugs and the canine antagonist accidentally plummet off a cliff, screaming hysterically and clutching each other as they fall for a ridiculously long time by the standards of a seven minute short. Director Tex Avery wanted to have them fall off yet another cliff after they survived the fall from the first one, but Leon Schlessinger cut Avery's ending, which prompted Avery to leave Warner for MGM. The cut part also alluded to a very risqué joke. Bug's after they fall again. "Hang on to your hats fellas, here we go again!"
A similar gag was done in "Falling Hare", with Bugs Bunny trapped in a plane which plummets down for a long time, with some hilarious takes of Bugs panicking and becoming sick to his stomach. It only stops just before hitting the ground because it runs out of gas.
On Tiny Toon Adventures, in the episode "Journey to the Center of Acme Acres", Plucky and Hampton fall down a crack in the ground when a huge earthquake hits Acme Acres. After a while, they start getting bored and hope they eventually hit something just to break the monotony. They eventually end up at the center of the Earth where they float because their gravity reaches an equilibrium.
Hamton: Think we'll hit bottom soon?
Plucky: I hope so, this is so boring. Getting splattered would be a nice change!
In The Flight of Dragons: "It seems like we've been falling for hours!" "Actually, it's been more like ten centuries!"
The episode "Shanghaied" has the Flying Dutchman throw Squidward in the Fly Of Despair because of his endless ranting. Squidward doesn't reach his house until near the end of the episode.
In another episode, Plankton uses a device to switch lives with Mr. Krabs, and he begins falling through a type of portal on his way there. While he is only shown falling for a few seconds before a flash, he actually stops mid-fall/scream, takes a drink of a soda he pulled from nowhere,and then continues to scream and fall.
In part 2 of the Phineas and Ferb episode "Phineas and Ferb's Hawaiian Vacation", Candace goes over a waterfall and falls screaming for about ten seconds straight.
In an episode of Dexter's Laboratory Dexter and Mandark fall down a hole and partway through take the time to scowl at each other.
The aptly named "Bottomless Pit" episode of Gravity Falls shows us a literal Bottomless Pit, funnily enough. The cast falling into it has time to tell four stories, among other activities, before finally reaching a halt.
Astronauts in orbit are actually in a state of freefall for the entire duration of their mission - it's just that the smart guys at NASA have figured out a way to throw yourself at the Earth and miss for days at a time.
Planets, moons, and satellites in orbit around stars. Stars flying through space. Anything flying through space.
A Low Earth Orbit has a period of about 90 minutes, so falling for hours would mean that you'd fall all the way around the world, multiple times.
In 1960, Joseph Kittinger, during testing on the feasibility of putting a man in space, rode a balloon to an altitude of 102,800 feet — over 19 miles up — and then jumped out. The resulting skydive lasted four and a half minutes and still holds several relevant records.