Seto Kaiba did this once in the Yu-Gi-Oh! anime; so did Edo Phoenix in GX.
Spoofed in the "New Year's Cleaning" episode of Keroro Gunsou, where Keroro does a Super Window Jump into the bathroom to tell Natsumi she's not cleaning the bathtub properly... only to get knocked back out the window for getting broken glass all over the floor.
In one episode, Keroro is watching a movie where a hero jumps through a window into the villains' lair. He actually thought it was open, though.
In Sumomo Mo Momo Mo, Uma Kamen bursts through a stained glass window in an outfit FAR too small to avoid the death of a thousand razors. None of the debris even reaches the ground to harm the non-martial artists in the wedding ceremony.
Matsuri busts through a stained-glass window early on in Sola, but she's immortal, so whatever.
Anita does this to rescue Nenene in Read or Die the TV Series, she does, however, cut a little "X" in the glass before impact.
B-Ko smashes a window in the palace section of the alien ship in Project A-Ko to get in. She's protected by her special (and skimpy) armour but somehow C-Ko, sitting motionless in the room, is unsliced.
In the Cowboy Bebop Movie, Spike jumps through a train window to get to the villain. He shoots the window first, so it'll shatter easily, and is apparently protected from injury by just being that Bad Ass.
In the CG-animated Appleseed, several cyborgs bust through the stained glass windows of a church to surround Deunan. In the sequel film, Briareos does it. Twice.
Zelgadis in Slayers does this as his stylish return to the series, also providing some much-needed reinforcements for the heroes.
Used totally straight in the Princess Tutu episode "Black Shoes", when Fakir jumps through a window to face the Dark Magical Girl—and then proceeds to pick up a glass shard from the window to use as a weapon. He has no powers that would protect him from the glass, and he's only wearing his school uniform...he's just fond of being very dramatic and badass.
The various MADMs from Ranma 1/2 would indulge in this from time to time, but there was a subversion early in the story: after being tossed out an open (third-story) window, Ranma bounces back up from a tree branch to get back inside... only to smack solidly on the pane of glass when Akane closes the window on him.
Subaru of Magical Girl Lyrical Nanoha jumps through glass windows at times, but it is eventually justified since she's revealed to be a cyborg
Mori the Ninja Maid does this in Haruhi-chan. Just for this trope, she and her butler partner get out a trampoline so that she can do this on the second floor of the school. "I'm just a passing maid!" Kyon: LIAR! Given her later abilities, she probably didn't need the trampoline.
In Tom Sawyer no Daiboken, the scene described below in Literature is quite dramatic. During Moff Potter's murder trial, Tom finally confesses to witnessing Injun Joe commit the murder. The villain tries to kill Tom, but is forced to flee by the sheriff and he leaps through the courthouse window, in slow-motion, with nary a scratch. But then, Injun Joe is pretty strong, not to mention huge.
Lupin III has many charactes doing variations on the trope. The titular thief has bailed through several windows, open and closed alike, in the course of his career. Lupin III (Red Jacket) had Jigen do it just before shooting down a helicopter with a revolver in the first opening sequence.
An immortal leaps out a window in Baccano!! to escape the one thing that can truly kill him.
Berserk's Skull Knight does this to a solar eclipse when he rides in to save Guts and Casca during the Eclipse.
Nichijou - When Mio sees her crush walking arm-in-arm with another girl, the first thing she does is jump headlong out the window and start running. And that's only the beginning...
In the Pandora Hearts anime, the Baskervilles make their first appearance by jumping through the windows in the church where Oz is having his coming-of-age ceremony. Given the Baskervilles' near-invulnerability to physical injuries, it makes sense that they are not shown to be injured as a result of this.
America from Axis Powers Hetalia did this twice in episode 13 of the fifth season. The first time he ended up with a shard of glass stuck in his forehead, although he was uninjured the second time. When a little kid asked him why he went through the window, he claimed it was because he had just gotten back from Hollywood.
Various incarnations of Spider-Man comics have Spidey regularly performing the trope as an entrance to shake up goons.
Miguel O'Hara, the Spider-Man of 2099tries to just open a window to slip out of his high rise apartment, but the windows are "sealed for [his] safety".
Characters from The Trigan Empire used to get away with this, despite the bare arms and legs exposed by their pseudo-Roman outfits. Trigo, for example, once escaped a room full of baddies by leaping through a window with his bare arm covering his eyes and his sandaled foot leading and maybe kicking the glass. Not a drop of blood anywhere!
Batman. At least he typically has an armored costume to handle the glass.
In one story in the Batman Black And White collection one-shots, Batman comes crashing down through a glass ceiling while the Joker is mid-speech. It turns out they're actors (...in a comic book), and as they head to the canteen after the shoot, Joker points out that Batman always gets the big dramatic splash pages, while Batman admits he wishes that he got to make speeches.
Like his mentor, Robin usually plays this one straight, but in one of the last issues of his own comic, the Boy Wonder tackles someone through a large window, and the internal monologue mentions, "I'm going to be picking glass out of my hair all night. Remind me why I just wear a domino mask again?" This becomes a "Funny Aneurysm" Moment later on, when half of his head is horribly burned in an explosion because of the lack of protection.
Rorschach from Watchmen jumped through a window to escape a building he had set on fire. Of course, it ended up pretty badly for him because he landed in a trash can, preventing escape from his pursuers, but still, he didn't seem to have any injuries from actually jumping through the window.
Although later we see that he has sustained some lasting damage to his ankle because he "landed on it badly" during the jump, and consequently injures it again when the Owlship crash lands in Antarctica.
Lucky Lukeexpects to have to get out this way when he enters a building, so he always parks his horse under the window. The only time it ever inconvenienced him in any way was when he did it through the wrong window and, instead of a dramatic horseback escape, got a painful stomach landing.
Once, he landed on a horse that wasn't Jolly Jumper. When JJ arrived, he explained to readers he put friends in each of the saloon's windows as he couldn't know which one Luke would escape through.
Subverted early on in Grant Morrison's Doom Patrol - Crazy Jane telekinetically smashes through a plate glass window, then ends up with shards in her hair and blood streaming down her face. Cliff then gives the shop owner the Doom Patrol's address so he can send them the repair bill.
The minor Marvel villain Mad Dog had what was largely considered his Crowning Moment Of Awesome when he attacked his ex-wife Hellcat's wedding; Just as they get to the part where the priest asks if anyone objects, he bursts through the stained glass of St. Patrick's Cathedral.
The National Lampoon did a parody of Nick Fury in the Nixon years - G. Gordon Liddy, Agent of C.R.E.E.P. - where Liddy entered every room in this fashion.
Lampshaded by Shiva in an issue of Birds of Prey when Cheshire jumps out of a window and Black Canary jumps out after her.
Shiva: Perfectly good set of stairs...
Ethan, Ashleigh & Skink do this from the Raven castle in Scion to escape from Bron. They land in water.
In Bookhunter, the Library Police's SWAT teams regularly smash through windows during arrests, and Agent Bay does likewise when he needs to get to the roof via fire escape in a hurry.
Sin City windows are made of Soft Glass since Marv and other characters have jumped out of windows in order to escape multiple times. In fact, in at least one instance, Dwight escaped by being thrown through a window. They are always unharmed, of course.
Lampshaded by Catwoman in Knightfall. Chased and outnumbered by enemy agents, she got into an empty room. She broke the window with a chair, hide behind the desk, and think "Let's see how stupid they are". The gunmen appear, saw the broken window, and understood that she jumped there. Hidden behind the desk, she thought "Very stupid!"
Yoko Tsuno has to do this in the "Devil's Organ" story, to make the Big Bad believe that she was dead.
The skylight variation is used in Kyon Big Damn Hero when Kyon interrupts a meeting whilst holding a spy.
The Dark Knight continuation fanfic A Piece Of Glass has OC Breech Loader throw a chair at a window, which only cracks. She uses the weakened glass and her running momentum to smash through it and drop three stories to the ground, to escape Arkham Asylum. The Joker, who was using her much louder escape as a diversion for his own, is very impressed.
In the My Little Pony fanfic Article2 it is subverted and deconstructed at the same time. Shane shoots the glass panel first to only then dive through it, and the cuts he suffered are very frequently mentioned.
In Diaries of a Madman, Navarone does this in order to escape from an amorous in-heat Celestia, though his wings take the brunt of the impact.
In the Anime/Blood+ fic Waking Dream, Reeve pulls this off to escape from Diva after she tries to drink his blood. He gets several shards of glass embedded in his body in the process.
Star Trek Into Darkness: Harrison crashes through a large glass window while fleeing from Spock, and gives it about as much attention as the air he was running through a moment before. Justified in that his genetic engineering makes him Nigh Invulnerable.
After running out of arrows in The Avengers, Hawkeye swings down and crashes right through a massive window. He isn't badly hurt, but his pained body language seems to imply that he got poked by a few pieces of glass.
While running from Ellen Brandt in Iron Man 3, Tony Stark jumps through a store glass window. His expression afterwards implies that it was painful at least.
In Captain America: The Winter Soldier, after the Elevator Action Sequence in SHIELD HQ, Cap jumps through the glass of the elevator all the way to the lobby using his shield. He does another version when chasing The Winter Soldier who had just shot Fury, jumping across the street and through a window. He does have the advantage of his shield to protect him compared to most examples.
And earlier when Cap grabs Natasha and jumps through a window to escape a grenade that's about to explode; in a blink-and-you-miss-it-moment, it's Natasha who breaks the window with a pistol shot just before they crash through it.
Averted in Lockout when Snow attempts to leap from one building rooftop to another, misses, slams into a window (which doesn't break) and falls to the street below.
Done in Batman to confront The Joker who has taken over the museum and it about to do something to Vicki Vale.
Batman Forever, Batman does this through a ceiling window to confront Two-Face after he crashes Edward's event.
Edward to Two-Face "Your entrance was good, his was better."
In Die Hard, John McClane does this and doesn't hurt himself, even though the rest of the movie realistically depicted him getting his feet horribly mangled due to the broken glass everywhere he had to walk on.
The first kick didn't break the window, though, forcing him to shoot the glass.
In the original Gremlins, Billy jumped inside a window, because the door was locked and he needed to kill the last gremlin. First, however, he broke through the glass with a toy vacuum cleaner.
Near the end of the movie The Game, Nicholas, who thinks he has just killed his brother, decides to commit suicide by jumping off the roof of the skyscraper he's on and falling through a glass ceiling. However, it's quickly revealed that the entire movie was a Gambit Roulette and Nicholas' brother predicted that he would jump off the roof (another person later thanks him for jumping, since he was supposed to push him if he didn't). Thinking ahead, he places an airbag on the ground and replaces the glass ceiling with safety glass to keep Nicholas from hurting himself. He is even told to keep his eyes shut while they remove the glass from him because: "even if it's fake glass, it can still cut".
The Bourne Ultimatum is guilty of this, where Jason Bourne leaps across an alleyway, through a closed window, jumps up and immediately starts fighting the assassin sent to kill him.
Superman II, when the three Kryptonian criminals invade the Daily Planet: "When are these people ever going to learn to use a doorknob?"
Played straight in Minority Report, though the people coming through the skylight were armored police officers who, impliedly, do this sort of thing on a regular basis. However, they were coming down into someone's bedroom, where they knew two people had just been having sex.
The eponymous character in Spawn. Justified with his costume and cape acting as armor and Spawn being undead and thus unharmed even by bullets. That, and the fact that the movie hardly takes itself seriously.
1994's The Shadow does a variation on this. Villain Shiwan Khan jumps out a window, to be sure, but he first breaks the glass telekinetically.
Bond smashes through a window unaided in a highly dramatic fashion in GoldenEye as he escapes interrogation.
In Quantum of Solace, both Bond and one of the fellows from Quantum manage to fall through a skylight after scrapping with one another, fall onto some scaffolding, and scrap for a single pistol in order to shoot the other bastard.
In The Wizard of Oz, Cowardly Lion turns away from the fake Wizard effect, sprints down a hallway screaming, and jumps out a glass window into some bushes.
Played straight in The Addams Family, when Gomez comes back to the house to rescue Morticia. Justified in that, well, if you can survive electrocution and consider torture foreplay, a little glass isn't gonna be much of an issue.
In The Mummy Returns Rick and Jonathan jump through a window, land on an awning, roll off that awning onto another one, and finally jump to the ground.
Subverted in The Parole Officer, when a character attempts to escape from a police officer in the bank he has just robbed by swinging out through a window, only to bounce off of it. He picks himself off the floor and sheepishly says "toughened glass" to which the officer replies "Its a bank!".
Subverted in the Made For TV The Wild Wild West movie. After knocking down the British agent who had captured them, they try crashing through the window to escape. Unfortunately, the window features a new invention - bulletproof glass. They bounce.
. . . and later on use a different trope to get away.
Done by the Bug to effect a dramatic escape in Men In Black.
Help! - the Beatles dive out the window in a pub to get away from bad guys.
And earlier, bad guys dive in the window of the Beatles' flat, taking them by surprise.
The Good, the Bad and the Ugly starts off with one. The introduction of Tuco (the ugly) consists of him crashing through a window to get outside after the building he's hiding in gets stormed by his enemies. In this case, he couldn't use the door because said enemies were blocking it.
The 1979 Universal version of Dracula has Mina, now undead (Lucy and her roles were switched in this film) escaping from a insane asylum like this after feeding on a baby and being discovered by the horrified mother.
Averted in the Tony Jaa movie The Protector. Tony's character is being chased by a four-wheeler down a hallway with large window at the end. Instead of jumping through, Tony runs vertically up the glass, and the four-wheeler crashes through below him.
Waring Hudsucker, in The Hudsucker Proxy, sets off the events of the film by impulsively leaping to a spectacular death through the window of his company's boardroom.
Later subverted when a lesser executive panics about the company's future and attempts the same thing through the same window, only to find the Big Bad had the window replaced with Plexiglass.
Deconstructed in The Matrix. Trinity jumps through a glass window and gets her face cut for it.
Deconstructed again in The Matrix Reloaded. Bane and Malachi jump through a skylight simultaneously. Even though they have shades on, Bane waits until the glass has settled before looking back up.
Done during the climax of Transformers: Dark of the Moon Sam, his girlfriend Carly, and the marines they're with have to jump out of a window of a tilted building, hundreds of stories up to escape a Decepticon chasing them they don't land on the ground per se but slide along the building till they're force to shoot the glass to drop to a lower floor or else fall to their deaths.
Used in the climax of Black Moon Rising, when Quint and Nina jump from a skyscraper to another with the eponymous super car.
Kane escapes from the Devil's Reaper by jumping thrpugh a stained glass window in Solomon Kane.
Total Recall (1990). Richter jumps through the front window of The Last Resort brothel to escape the firefight going on inside.
Played for tension rather than Dynamic Entry in Mission Impossible Ghost Protocol. Ethan Hunt has to free-climb up the outside of the highest building in the world to get to its well-protected server room. He does so using adhesive gloves, but as he's cutting his way through the glass, one of the gloves malfunctions. Cue Climb, Slip, Hang, Climb sequence, but Ethan's dropped his laser cutter so has to smash his way through the partly-cut window. It won't break, so he has to swing outwards (hanging by his one remaining glove) and kick his way through.
Averted in The Krays (1991). Jack the Hat tries to throw himself through a French door to escape being killed, but just gets stuck in it, easy prey for the gangsters who simply haul him out.
Interestingly, in light of the notes on vampires above, Dracula, in the Bram Stoker novel of the same name, only does this once despite his preference for windows above doors. In other instances, he either slides into cracks between the window and frame, or he has something else break the glass for him. In the example of this trope, however, it's daytime and he can't change forms, but is still tough enough to just leap through the pane.
Allegiance has Mara Jade performing this trope, though she uses fancy Force-assisted acrobatics to cut a round hole before she actually hits it. She does this to both a stone wall and a window, and notes that the window was much easier.
Mistborn: The Original Trilogy: The Final Battle of the first book takes place at the top of a tower whose exterior wall is made entirely of a single, cylindrical sheet of multicoloured stained glass. Vin, whose Mistborn powers include Not Quite Flight and shooting coins, enters by first piecing the glass with a series of coins, then crashing through the weakened section. The scene is written from the perspective of one of the villains, who first sees a single coin shoot through the glass and roll across the floor, then more coins, then POW. Brandon Sanderson knows how to write awesome.
Buffy and Faith actually use this as a weapon in "Bad Girls" when they burst into a vampire nest through a blackened window in broad daylight, setting one vampire on fire and causing the rest to flee in panic.
Spoofed when Angel does this and later complains about being billed for the broken window.
But the Fourth Doctor did it first. And headfirst. So there.
The Fourth Doctor also did it a second time - leaping straight down through a ceiling skylight to ambush the enemies in the room, defeating them all in the confusion with only his bare hands, retrieving someone's gun, pointing it at the room and announcing "I win".
In The Adventures of Superman, George Reeves as the title character wouldn't bother finding a window — he'd just break through a wall. (One, he's Superman, dammit — and two, foam and papier mache debris was cheaper and safer than stunt glass.)
Ray Kowalski on Due South did this on a motorcycle once.
Claire Bennet does this on Heroes to get away from the Petrelli clan. And honestly, if Mama Petrelli cornered me in my real father's office, and he were on her side, and I knew I'd regenerate from any wounds I suffered anyway, I'd jump out a 10-story window, too.
He does this again in the season 2 premiere, when he's trying to escape from Cameron after she'd temporarily gone rogue.
Omar Little did this to escape certain death on The Wire. Unusually for the trope he was badly injured by the move, but it was from a fourth-floor window. This was taken from Omar's real-life inspiration, Donnie Andrews, with one difference: Donnie jumped from the sixth floor. The TV show had to turn it down to make it believable, and even then...
Marlo Stanfield: That's some Spider-Man shit right there.
Col. Flagg tries this in an episode of M* A* S* H, after telling the others in the room to look away since he has to leave like the wind, traceless. Crash.
Hawkeye: [Looks out the shattered window] "The Wind" just broke his leg.
In Father Ted, Father Jack repeatedly exits the parochial house by jumping through the window, whether it's fleeing in terror from a nun or just because he can't be bothered to use the door. Subverted when they install the Plexiglass. The window remains undamaged as Jack bounces to the floor.
When Seth Green gets Punk'd, the setup involves a supposed raid on an illegal casino, requiring at least one federal agent to enter by somersaulting through a window. In the post-prank interview Seth Green recalls thinking "that was really unnecessary".
Happens in the last episode of Birds of Prey when Barbara and Dinah swing into their villain-occupied headquarters through the gigantic clock tower window.
Done a couple of times in Highlander: the Series. It helps when you know you're immortal and will heal within minutes.
Slan Quince both enters and leaves this way when he first introduces himself to Duncan. (Complete with rubber sword blade hilariously boinging around in the slow-mo exit after hitting the window frame.)
Richie Ryan escapes out a second-story warehouse window on a motorcycle.
Mika, Pete, and Claudia of Warehouse 13 all get trapped inside a house stored at the eponymous Warehouse. If they try to leave, the house simply warps space so that they are instead entering the house again. So Pete does the (semi) logical thing to do and jumps through a window instead. ...Which causes him to jump in through the window right next to it.
SCTV - hippie tv show host Dr. Braino (John Candy) gets too high and does it - then does it again in the only other skit he's in.
In the second episode of Third Watch, Maurice "Bosco" Boscorelli tackles an armed felon and they both go through a second floor window.
Daniel Jackson pulls this in an episode of Stargate SG-1. He has to shoot the glass ahead of time, but manages to get through without injury (of course, the radiation on the other side was not so accommodating).
Sam and Dean in Supernatural do this to escape from the demon Alistair. Unfortunately for them, they aren't made of steel - the following scene has them pulling shards of glass out of their bodies, and Dean even having dislocated his shoulder from the fall. It's logically treated as a Godzilla Threshold sort of thing, with their options being "jump out the window and hopefully survive" or "stay inside with the angry psychopathic demon with skills in torture who just laughed off our magic demon-killing knife."
Season 2 Opener of Sanctuary has Ashley and her squad of near-vampires entering through sanctuaries throughout the world through their skylights and proceed to tear things apart.
A 24 Day 8 episode deconstructed this; a suicide bomber broke out of the window when he was surrounded by Jack Bauer and his crew, but ended up limping as he walks into the oxygen chamber.
The A-Team does this frequently. Usually by Murdock.
In Danger 5, this is done Once an Episode by no one other than Hitler. The Danger 5 team, having fought their way through another slew of improbably freakish bad guys, will confront Hitler only for him to escape through the nearest window. Head first. Sometimes while he's duel-wielding machine guns. And in a Running Gag, it's always Stock Footage from the first time he does this. Our heroes only succeed in killing him (or so they think) when they finally corner Hitler in an undersea base which doesn't have windows.
White Collar: Neal grabs a banner, cuts one end free, and dramatically swings across a courtyard and straight through the window on the other side.
The X-Files, episode "Colony": One of the clones jumps through a closed window to escape the alien bounty hunter.
The Scarlet Pimpernel (the 1999 miniseries): In the first episode, Pimpernel throws himself against a closed window in order to escape from Chauvelin after those two confronted each other in a French café.
Tori Amos executes a particularly random one a few seconds into the music video for "Pretty Good Year," jumping into a building. The scene replays in reverse at the end. Chalk it up to the 'supernatural creature' category.
Billy Idol rides a motorcycle through a stained glass window in the video for "White Wedding".
Harsher in Hindsight: While it didn't involve crashing through windows, he would later be injured in a motorcycle accident several years later.
Lampshade hung in Sa Ga 2: The main character's father always leaves buildings through windows, leaving the other characters wondering aloud what the point is.
In Resident Evil 4, Leon is capable of jumping through windows without injury, simply by covering his face, which is good, because he tends to exit buildings this way. He also almost never climbs down a ladder.
Leon really takes it to the extreme in this game. Almost any window you can walk up to can be leapt through with no consequence (and thanks to the giant flashing button on the screen, it's encouraged). Leave a house through the door? NEVER; OUT THE SECOND FLOOR WINDOW! Climb down a ladder in the three story tower? NO, JUST JUMP STRAIGHT DOWN! It's worth noting you can break a window and still jump through it, but it often just has Leon hop over the windowsill instead of diving through it.
Hell, even Ada, who's wearing a skin-bearing qipao, can pull it off exactly like Leon, without getting a scratch.
Once during the campaign, while zip-lining INTO a window.
In multi-player, diving through a window into a prone position, then offing an opponent within 2 seconds or so will get you a gamerscore achievement.
Averted in the old click and drag game Uninvited, any attempt to break the windows to get out of the haunted house lead to you bleeding to death; no you can't clear the shards with a chair or something; it just doesn't work.
Possible in Deus Ex, but only with ceiling glass, and unless you have something soft to break your fall or the right augments it will likely result in broken legs.Impossible to do with windows, as they have to be shot or otherwise broken before making the jump.
Also doable in Deus Ex: Human Revolution, again only with ceiling glass, and only in one spot while infiltrating the port in Hengsha. You do need augments to avoid killing yourself in the process, but it can be done completely stealthy (by activating your cloak before breaking the glass).
In The Legend of Zelda: Twilight Princess, Link, in wolf form, has to break through a window to get into one of the buildings. It's not particularly dramatic, but it is effective without being harmful to Link.
Possible by crouch-jumping through a window in Postal 2, though realistically you take a bit of damage. The police also tend to get very perturbed when you do it around them.
Assassin's Creed: Revelations: Altaïr crashes through the big window behind the Mentor's chair during his escape from Masyaf. It's a bit of a Despair Event Horizon since he's forced to leave the castle he called home in the hands of the Big Bad, not to mention the fact that he's leaving his wife's corpse in the garden.
All units in XCOM: Enemy Unknown can, and will, bash their way through glass windows when they need to get to point B. Justified, as your XCOM soldiers are wearing body armor (and later Power Armor), the aliens are rather callous towards their infantry and most are strong enough anyway, and any surviving civilians during Terror missions are probably desperate/terrified enough that they won't care about the potential injuries.
Hilarious example in Fate/stay night: in the Heaven's Feel path, Shirou and Kotomine have to quickly escape from a castle. Kotomine jumps out the window, and Shirou, after a moment's hesitation, follows. Problem is: they're on the eighth floor, and Kotomine is a very experienced magus who knows how to soften his landing. Shirou barely avoids crippling physical damage (he notes it's a miracle he didn't break anything), and afterward all his companions are staring in wonder at what a colossal idiot he is.
Doable in Command & Conquer: Renegade. Most windows that are big enough to jump through are breakable, which means if you get pinned down in the upper floors of that Hand of Nod you can make a hasty exit through the window.
Averted with PAYDAY: The Heist. SWAT will usually use explosives to destroy windows before rappelling inside. You can't jump through a glass window yourself; you have to shoot out the glass first.
Thematrix Path Of Neo has a few examples. Notably, the SWAT teams on the skylight version, and Neo doing a normal window version to try and save somebody, being Made of Iron Neo doesn't take any damage.
Homestar Runner features its own take on this, with Strong Bad's action hero alter ego Dangeresque, who often goes out of his way to make this exit (preceded by his Catch Phrase "Looks like I'm gonna have to jump!")
Critic: * crash* Aaaaaahhhhh....! * thud* My God what a tall building!
Adam Dodd in v3 of Survival of the Fittest escaped a grenade thrown into the barracks he was hiding in by jumping off a cot and through a window, somehow avoiding injury.
Parodied in Code Ment. When Lelouch jumps out of a second story window, a corresponding clip from Resident Evil 4 plays as a sort of "stunt double".
One DarwinAward was given to a salesman who ran into a window to show how strong it was. When the window was installed on a skyscraper. However, it was subverted in that the window didn't break, the frame holding it did.
In the Whateley Universe, Tennyo does this during the Halloween invasion of Whateley Academy, to get two students she's carrying out of the line of heavy machine gun fire aimed at her.
's Speed Highway has a tall building with a glass structure jutting out the sides; Sonic breaks the glass by standing on it for a second. From there, he runs down the building without being injured by falling shards.
In The Rifters it's not very obvious, but this is how Jo gets into Carnby's tower (see here)
Sal Walters, one of the alien-enhanced abductees in It's Walky! jumps in and out through upper story windows more often than not, leading comments from her boyfriend about all the broken glass. The Big Bad eventually gets to cause an excellent anticlimactic moment with Sal-proofed windows. (She then promptly bursts through the floor, but it was a good try.)
Happens to not just Elan, but to Belkar and Miko too. Given that they're already bloodied from their fight, it's impossible to tell whether any of the wounds are from the broken glass. And of course, being moderately-high level D&D-based characters, they're explicitly far more durable than real-life humans.
Subverted in Megatokyo: "Great Teacher Largo" jumps through a window to escape Ping, and badly hurts his leg. It later bites him in the rear in a DDR match.
Ellen tries this in El Goonish Shive shortly after her creation and subsequent Cloning Blues, with added coolness from making her duplicate (or original?) throw her at the window. The coolness factor is negated when the window lacks any glass. And is a story up. THUMP.
In The Adventures of Dr. McNinja, Dr. McNinja gets the jump on some thugs by entering the warehouse via the skylight. This comes immediately after he asks himself "What would Batman do?"
In Homestuck, Roxy's favorite means of transportation involves jumping through portal windows, though she tends to break them first. Dirk however, in the "[S] Dirk: Synchronize" animation, does several bona fide breakings through windows on his rocket board.
The creator of Antics said "if I ever draw a window, you better believe something is about to bust through it"
In the Futurama episode "Less Than Hero", the mayor attempts to summon the New Justice Team - Actually Fry, Leela, and Bender - while they're right in front of him in his office. In order to not blow their identities they quickly make up excuses; Fry declares that he can't take life anymore and jumps out through a window, and instantly returns in-costume through a different window.
In The Grim Adventures of Billy & Mandy, when Billy is scared by Grim and Mandy dressed as clowns, he throws himself out the window to escape, then immediately reenters the house, only to be scared again and jump out the other window. This continues until every window is broken. When Billy realizes he's run out of windows, he runs over to a neighbor's house, politely knocks, enters the house and jumps out ''their'' window.
Stewie does this in one episode of Family Guy; when it happens he's replaced with a very noticeable Stunt Double.
Subverted for laughs at the start of the My Little Pony: Friendship Is Magic episode, "Dragon Quest". Fluttershy rushes towards a closed window in panic, enters a 'ready to jump' pose, and... gently opens the window in an exaggerated manner before continuing her jump.