Hollywood Skydiving

Parachuting is a precise science in real life. There is only a small window on any given jump to deploy one's parachute; too soon, and you could risk breaking a leg or veering too far from the drop zone; open too late, and you might not have enough time to cut away and deploy your reserve should the main canopy malfunction at such a low altitude.

Hollywood ignores this. In the movies, as long as you deploy your parachute before you hit the ground, you are A-OK. Doesn't matter when you pull it, or if you're carrying heavy baggage, or if you're upside down, or if the parachute is tangled. Parachute injuries simply don't exist.

Also note that in Real Life, first-time skydivers are always either accompanied by an experienced trainer who will be literally strapped to the newbie's back or their chute will be opened automatically by means of a static line. Acknowledgement of this is slowly making its way through to the writers/producers, but there are still plenty of times when the only training a newbie gets is being pushed out the door.

This trope's prevalence can probably be traced to Rule of Perception. HALO jumps are to be excluded - they're basically this trope. And they're risky.

Anime and Manga

 * Averted in Gundam Wing: During one early episode the apparently-indestructible Heero Yuy jumps from a skyscraper and, owing to his conviction that "life is cheap, especially mine", doesn't deploy his parachute until a certain girl screams his name. By that time it's too late - he deploys it, it does nothing at all, he hits a cliff face and breaks his leg right in two. He later sets it, with his bare hands and no anaesthetic, while rolling around on the floor.

Film

 * Used in Quantum of Solace. James Bond and his girl not only deploy one parachute for both of them, but they do so two feet off the ground and while rolling through the air, a move which would be virtually certain to kill them both in real life. But they're perfectly unharmed.
 * Averted in Tomorrow Never Dies, as the HALO jump (High Altitude, Low Opening) is an actual military practice
 * Point Break.
 * Which was mostly busted by The Myth Busters (It was possible to catch up to a diver with a head start, the rest was pure Hollywood bunk.)
 * The catch up was not possible in the scenario shown in the movie. They would have either had to jump from a much higher altitude, or the first guy out would have to have much less of a head start.
 * The Mighty Morphin Power Rangers went sky diving in the first scene of the Non Serial Movie. Bulk and Skull ended up on the same parachute and off target, landing slowly into a building site (the one where Ivan Ooze was dug up). Could've been worse - they were about to jump without their parachutes, but Kimberly stopped them with a "I think you guys forgot these.".
 * Averted in The Skydivers: one diver waits too long before deploying his chute, and goes splat.
 * In the Get Smart movie, Max jumps (accidentally) without his parachute. Agent 99 jumps shortly after (it's got to be at least a minute or so), with one, catches up with him and grabs him, manages to do all kinds of stunts involving an enemy agent, and manages a perfect landing anyway. With Max.
 * Of course, the bad guy gets his chute cut up by 99 and survives his landing anyway, so they weren't really trying to be realistic here.
 * Averted in the new Star Trek movie. The Red Shirt, true to his name, screws around on combat adrenaline and goes floof when he gets sucked into a vent because he doesn't open his parachute when ordered to and drops too far. Meanwhile, Kirk and Sulu nearly get turned into parachute pizza themselves, and they actually timed it correctly.
 * Averted, if this were a skydive; However, space-diving changes the game a bit.
 * At the beginning of Bridget Jones: The Edge of Reason, Bridget is ordered to jump out the door without a trainer, and deploys her parachute a little too late. She ends up landing in a vat of pig excrement, but enough about the script.
 * Averted in Transformers: Revenge of the Fallen: Galloway does not wait till the last second to pull the ripcord.
 * "Not yet you dumbass!"
 * Subverted in The Bucket List, in which the two main characters, both elderly men, go skydiving for the first time. Both are performing tandem jumps (each man accompanied by an instructor), although there is a bit of dialogue during the scene, which the Myth Busters proved impossible (see the Point Break example above).
 * The opening action scene of the first Charlies Angels movie.

Live Action TV

 * An episode of Drake and Josh about skydiving has a very long sequence that seems to use every single gag known to man about jumping out of something. Or not.

Video Games

 * Virtually any video game with a usable parachute adheres to Hollywood Skydiving. Grand Theft Auto: San Andreas, in particular, comes to mind.
 * Pretty well justified, if they made it realistic and interactive it would probably cease to be much fun.
 * Saints Row 2 lets you pop the chute 2 cm from the ground and it immediately opens and you're okay. Then again you can also parachute out of a helicopter on top of another one without ill effects, while your original helicopter plummets out of the sky because your character apparently turned off the engine on his/her way out. And while you CAN jump out of a business jet, you are about 99% likely to smack into the wing and fall screaming to the ground without an opportunity to open your chute.
 * But that's okay because pulling off a perfect (3-gold-star) skydive, landing squarely in the back seat of a nearby gang car, grants you complete immunity from fall damage, thus enabling you to jump out of a helicopter far above the skyscrapers, fall for about a minute, and then do a nose-grind along the asphalt, without taking any damage whatsoever. This goes well with your immunity to car crashes until your car blows up and your own character's resistance to things like point blank machine gun fire.
 * The opening scene of Metal Gear Solid 3 has Jack arrive at the site via HALO jump (i.e, plane's about 3-12 miles up, he falls at 150 MPH, he doesn't pull the cord until he's about a mile up), but since he's a Green Beret, member of the FOX Unit, and all-around pretty cool character as well, it's OK.
 * All of the Battlefield games except for the first Bad Company game feature a Magical Parachute that comes standard in every footsoldier's backpack. It's deployable anytime while airborne and slows you to a safe speed instantly, resulting in silly (but very useful) scenarios like using a parachute to safely jump off a tall building, or to bail from a jet, free fall for a minute, and deploy the parachute just before hitting the ground. Oh, and you can use it as many times as you need to without all that obnoxious repacking.
 * Averted in Wii Sports Resort. In the "Air Sports" skydiving game, the player jumps out of an airplane and has three minutes to link up with other divers for photographs. The chute opens automatically with ample time to spare, avoiding the trope.
 * Except for the fact that a three minute free fall would require about 35,000 feet of altitude, which would only be accomplished through the use of high altitude HALO gear, and the chutes opened rather low, in reality, that altitude would only be a few seconds from the ground. Also, and automatic opening from an AAD is truth in television, but no one would ever actually rely on it.
 * The "ribbon parachute" from MDK might count. It works like a charm no matter if you're jumping off a six-foot ledge or from orbit.
 * In the indy computer game "Spelunky" The parachute item will automatically deploy after falling for a certain amount of time, and will save you from being hurt even if you are inches from hitting the ground.
 * In Tomb Raider Legend, Lara performs a BASE jump to enter an abandoned military base in Kazahkstan. As part of a interactive cutscene/quick-time-event, the player has to press a key at precisely the right moment as indicated by the screen and by Mission Control yelling in your ear, in order to deploy the chute. If Lara deploys the chute too late, she falls and dies.
 * Just Cause 2 kind of zigzags this trope. On one hand opening your parachute too high won't cause you to suffer any damage when you land, but opening it too close will cause you to suffer a slight degree of damage that fortunately heals rather quickly. Humorously you have an infinite amount of parachutes available to deploy and it is possible to go parasailing by using your hookshot to propel yourself. On top of that you can even buy rocket propellers for your parachute to fly yourself around. You know a game is fun when the act of falling out of the sky is so fun you could do just that and not get bored with the game.
 * World of Warcraft parachutes (the player-deployed kind, not the automatic ones that the game sometimes provides) are a bizarre case. They work instantly, so you can fall as far as you wish, deploy your flexweave underlay half a second before you hit, and suffer no damage. However, they only last a short time, so deploying too early can find your parachute expiring while you're still far off the ground.

Western Animation
"Pilot: Wait a second, did he just jump now?
 * Spider-Man and His Amazing Friends: Spidey lounges on top of the Kingpin's parachute. For comedy purposes, I suppose, since every iteration of Spider-Man ever can make parachutes out of webbing.
 * The "jump whenever" part of the trope is averted and lampshaded in the second season finale of Archer; Archer spends a good two minutes monologuing before jumping and ends up miles away from his drop point. You can see a light in the background go from red (no go) to green (go) and back again before he jumps, and the pilot quickly calls in and asks why the door was left open for so long.

Other agent: Yep."