"A good landing is one you can walk away from. A great landing is one where they can use the plane again afterwards."
— Common aviation proverb
Everyone's encountered or at least heard of this fellow. He's the Patrician of Demolition, the Czar of "Fubar", and the Master of Disaster.
He's supposedly an accomplished captain/pilot/driver, but whenever he gets behind the controls of any vehicle, he crashes it.
Even if he's in the desert with nothing to crash into, he'll somehow find a way. To his credit, having a reputation for crashing repeatedly means his crashes are, at the very least, survivable, so he does have that going for him.
Sometimes the crashes are not his fault; he just seems to attract bad luck. Still, with all the crashes he's been in, it's a wonder anyone trusts him to drive or his license hasn't been revoked. His insurance rates are probably through the roof. Is often depicted as Innocently Insensitive or a Nightmare Fuel Station Attendant, if not an out-and-out Cloudcuckoolander. "Crash course" puns are obligatory.
This trope can be convenient for characters hiring or having a pilot - no one else wanted Captain Crash, so he was available.
Can be somewhat justifiable for rookies crashing planes, because taking off and flying are much easier than landing. The landing is where the real skill shows itself.
Sister trope of the Disposable Pilot, who generally doesn't even survive his first crash. See also: Drives Like Crazy.
It's so bad, that even his coma delirium mocks him for it repeatedly (and even has him crashing a bicycle!) in the episode Phantasm.
Though not nearly as much as Alto in Macross Frontier, who trashes a new plane every other episode or so. In the epilogue, he managed to set his perfectly-undamaged Valkyrie on fire, after the battle was over, and scuttled it as it was breaking apart.
Seta in Love Hina usually enters a chapter by crashing his van, but emerging without major injury. His protégé Keitaro picks up the trait by the final chapters.
They're rarely the ones piloting them, but there's a rule that if someone of the Joestar bloodline gets into a plane, it will crash. No exceptions.
Cars, trains, boats and submarines have a similar tendency to crash somehow when a Joestar is near. Oh, and an helicopter, but that was highly intentional.
Joseph, in particular, is the king of this, having crashed at least 4 planes, one ship, a submarine and a car during the course of his life. The fun part is that when he was a kid, he dreamed of being a Royal Air Force pilot like his father. (He became a stockbroker instead.)
Sagara Sousuke from Full Metal Panic! seems to be this. Of course, part of it might be explained by how most of the instances where he's driving have been dangerous car chase scenes (where it's only natural that he would be crashing through things and driving crazy). But then one starts to wonder when, during an instance where he wasn't even being chased, he ended up running an obvious red light and crashed into another car. And then there's his crazy "driving" when he was riding on a bicycle... honestly, people should get the idea and just not let him drive.
Area 88: While very much an Ace Pilot, Shin Kazama manages to get at least three or four planes shot out from under him, depending on the continuity. His luckier comrades also have tendencies in this directions. The rest, well, Anyone Can Die.
Mobile Suit Gundam Wing: Heero Yuy. Utterly lethal in mobile suit combat, but the number of suits he's totalled or seriously damaged defies belief. He has had at least two Leos and the Mercurius shot out from under him, as well as wrecking Wing Zero in Endless Waltz (although that took some doing.) And then there is Wing Gundam. Poor, poor Wing Gundam. To date, Heero has crashed it into the ocean, attempted to self-detonate it, attempted to blow it up with torpedoes, actually self-detonated it, then finally had it shot out from under him before getting his Mid-Season Upgrade. One has to wonder what Trowa was thinking when he lent him Heavyarms... Ironically he actually got Heavyarms through that mission totally intact.
In Gundam SEED and Gundam Seed Destiny Kira Yamato and Athrun Zala have each had only one of their mobile suits survive the end of the series (one each across two series), every other suit they used was totaled, though Athrun went though far more suits, to the point if he touched it it was probably doomed and Kira's tended to be rebuilt and destroyed again. To be specific Athrun self destructs Aegis to fight Kira, self destructs Justice to stop the Genesis laser, and gets Savior damaged beyond repair by Kira. Kira meanwhile gets the Strike wrecked against said Aegis selfdestructing (It's repaired and given to Mu, who gets it completely destroyed), gets Freedom wrecked against Rau in the final battle of Seed. In Destiny Freedom is repaired and Kira pilots it again, until Shinn also wrecks it, this time beyond repair. Only their final Strike Freedom and Infinite Justice units manage to remain unwrecked.
And then there's Patrick Collasour from Gundam 00, whose habit of being shot down in every single mission he's assigned to, but always surviving for the next, became a Running Gag for the show.
In Gunsmith Cats, Rally Vincent wrecks her car on multiple occasions despite proving her worth in multiple street races. At one point it is even mentioned that she can't get insurance anymore.
Enryu from GaoGaiGar has a tendency towards this, despite being a transforming fire truck: any time he's launched out of the Mirror Catapult, it can be safely assumed that his return to the ground will be devoid of any grace whatsoever. And apparently his Chinese counterpart, Rairyu, shares the same problem, as do both of the French Dragons, Kuryu and Anryu. 2/3 of the Dragon Braves, it seems, are masters of the divine art of the faceplant.
Rosette Christopher of Chrono Crusade has gotten into so many car accidents that even the mangaka isn't sure whether or not she has a license.
In the manga adaption of Kingdom Hearts, Sora takes control of the Gummi Ship at one point... and rams it into a meteor near Traverse Town, causing Donald to furiously ban him from the controls.
Donald himself seems to show signs of this trope when he accidently grabs onto a Magnum Loader and causes it to go wild all over the place while Sora and Goofy try to help him. Played for laughs, mostly, until he crashes into Tron, causing the latter to drop a required piece of data and destroy it.
Whenever we meet Spaceman Spiff in the Calvin and Hobbes comics, he's crash landing on some planet.
There's a Shout-Out to this in the card game Cosmic Encounter, with the "Spiff" race, who have the power to "crash-land" when they lose a battle.
Also, Calvin rarely pilots his sled or wagon without flying off a ravine or crashing into a tree.
Almost everyone in Sin City crashes his or her car, often due to Car Fu.
In the Lucky Luke episode Going Up the Mississippi the machinist, "Bangs", is stated to have exploded fourteen river boats. Subverted in the end: This time the other boat explodes, much to his surprise.
Cyclops of the X-Men is this. Starting when he was orphaned during a plane crash (although aliens were involved), then there was that time with the first mission of the new X-Men, then once with Lee Forrester, then again with Storm and Xavier. Other characters have started calling him out on this.
In Luna's Power and Rainbow's Love, Luna spends the first two chapters poking fun at Rainbow Dash's tendency to crash. It doesn't help that Rainbow pretty much starts the story by crashing into a tree.
The X-Wing Series gives us Ascended Extra Derek 'Hobbie' Klivian and his much-lampshaded tendency toward spectacular crashes and long periods in a bacta tank. Despite this, he's unquestionably an Ace Pilot and even seems to make it work for him: no matter what violent fate befalls his vehicle, Hobbie will always eject, survive and be back kicking ass within the week.
The first-published comic arc in that series, The Rebel Opposition, makes it necessary to mention Hobbie's squadronmate Tycho. He put on Imperial guise and reported in saying that his TIE had crashed. They gave him a new one. He flew on a mission, was shot down by his own X-Wing (long story), ejected and survived, then returned to the Imperial base. They gave him a new one. Then he betrayed them. In fairness, TIE fighters are light, cheap, unshielded Fragile Speedsters mainly used for Zerg Rushing.
'Face' Loran's backstory notes that he essentially bought his way into Starfighter Command, including buying his own starfighter... and on not one, but two occasions, a replacement fighter after being shot down.
Face's wingmate, Ton Phanan, is stated near the beginning of Wraith Squadron to have trouble landing. Furthermore, he loses no less than three fighters during the course of the series (though the first was just bad luck, and not really his fault). He's mortally wounded after the last one, though Face does at least manage to speak with him one last time.
Starfighters of Adumar includes the character of Tomer Darpen, nicknamed "Ejector" after a notorious crash landing in which his Ejection Seat fired after he managed to get his fighter stopped.
Sometimes it's because they're drunk. On fermented nectar. Yes.
Q makes a point in some of the later James Bond movies of asking 007 to bring his gadgets back in one piece. They never do, especially the cars.
Natalya Simonova: Do you destroy every vehicle you get into? Bond: Standard operating procedure.
The absent-minded Admiral Benson in Hot Shots!! gives us this line:
You know, I've personally flown over 194 missions and I was shot down on every one. Come to think of it, I've never landed a plane in my life.
Trinity in The Matrix. She's a great fighter and one of the best characters, but make sure you aren't in a car, helicopter, or motorcycle with Trinity at the wheel! (Granted, most of her crashes are either deliberate, or happen because she didn't need the vehicle anymore and had no time to do anything but jump off and discard it while it was still running.)
A romance novel where the hero, an airplane pilot, was called "Crash" ... because he crashed a car.
Marco from Animorphs apparently hates trash cans. To be fair, he was a teenage gorilla without a license.
Harry Potter is a natural flier, but people seem to love making him crash or fall. In Chamber of Secrets, he spends most of the Quidditch scene dodging a Bludger jinxed to go after him in particular. He catches the Snitch, only for the Bludger to break his arm and send him into the mud. In Prisoner, he blacks out and falls off the broom when Dementors invade the stadium. In Order of the Phoenix, Crabbe hits a Bludger at his back out of spite right after he catches the Snitch.
Callista Carmel of Tour of the Merrimack earned the nickname "Crash Carmel" for totaling a number of shuttles.
Live Action TV
Lt. Frank Drebin of Police Squad! (1982) would park by smashing his car into something (trash cans, bicycles, other cars) at least Once per Episode. The running gag is that in the first episode he hits one trash can, two in the second, three in the third, etc. The series was cancelled before this got truly ridiculous.
Possibly "borrowed" by Sledge Hammer! four years later as a running visual gag for Sledge, whose car was a bright green disaster area on wheels driven by a man whose parking skills were as bad as Drebin's.
Although being a competent pilot, Boomer in the re-imagined Battlestar Galactica is known for her terrible landing skills, causing a dent on her ship every time she lands.
Racetrack and her co-pilot Skulls fall into the bad-luck variety. There is nothing to show that Racetrack is a bad pilot. That doesn't change the fact she seems to attract errors, breakdowns, sabotages and attacks. Did the striking workers spike the fuel, casing a Raptor to spin out of control and crash into Colonial One? It'll be Racetrack's. Did chief mess up the repairs and caused a Raptor to crash on the landing deck? It's Racetrack's. Did a saboteur plant a bomb in a Raptor to kill Baltar's attorney? It's Racetrack's Raptor. Did the experimental jump drive cause a mis-jump? It was Racetrack and how she discovered New Caprica.
And yet she manages to perform a post-mortem Deus Ex Nukina, taking out the Cylon Home Colony with her.
Lee "Apollo" Adama should also bear mentioning. He doesn't necessarily wreck a lot of stuff, but he has a penchant for wrecking important stuff. From the mini-series he manages to first disable his father's old fighter and then utterly trash it before the the end. He goes on to wreck the only stealth fighter another character spend an entire episode fabricating. And then he wrecks The Pegasus, the more advanced of the pair of battlestars. It's a wonder why Daddy keeps giving him the keys.
Richard Hammond of Top Gear has a... not-undeserved reputation for being accident-prone.
This is pretty much Chakotay's nickname in Star Trek: Voyager. He ends the second part of the pilot episode crashing his original ship into a Kazon cruiser, and nearly every shuttle he touches from then on is doomed.
Inevitable. The pilots seen on the show either handle the incident very professionally, committed errors that caused the incidents, or were victims of hijacking attempts. On two occasions, the show covered a pilot who may have purposefully crashed the plane in a murder-suicide.
Captain Lutz of Crossair Flight 3597 was almost literally this before his fatal accident, and yet his airline continued to let him fly.
The Fleet Air Arm squaddie song "The A.25 Song" which begins as: They say in the Air Force that landing's okay/if the pilot can get out and still walk away/but in the Fleet Air Arm the prospect is grim/if landing is poor and the pilot can't swim. Each of the twenty or so verses of the song describe the protagonist crashing his aircraft in various ways. The A.25 is the Fleet Air Arm damage report form, very detailed and notoriously agonous to fill.
Captain Jet Morgan of the old BBC radio serial Journey Into Space could fit this trope. He captains the spaceship Discovery, and when it's required that the ship lands, Jet is always the one who pilots her down. Unfortunately he tends to crash, or at least make hideously bumpy landings, more than he manages to bring her down smoothly. Of course, one of those times he had actually been knocked out before the ship was quite fully landed, but most other times it's just Jet. Nobody ever really comments on this.
It may also count that he does extensive damage to a Martian asteroid ship when he tries to slow it to a stop. Granted, it doesn't actually crash—they are in space, after all—but it does the next best thing.
A naval example in The Navy Lark, Mister Phillips's standard method of docking is this trope. He caused more damage to Naval property than both world wars.
Ironically, the one time he was asked to deliberately crash HMS Troutbridge into another ship (as part of a ploy to allow Captain Povey to escape his overbearing mother-in-law and join the rest of the crew at a pub) a fault in the steering mechanism ensured he couldn't hit anything... 42 times in a row!
Resident Evil: Leon is this to Running Gag levels. If he gets behind the wheel of a vehicle, ten-to-one says he's gonna crash it or it'll end up destroyed pretty soon. Actually lampshaded by Ada in 4, where she immediately recognizes a busted bulldozer as "Leon's handiwork." Justified to some extent, as typically when he's driving said vehicle there are monsters attacking and trying to eat him; anyone would have a hard time concentrating under such conditions, but one would expect he'd get enough practice to eventually learn how to drive safely in a crisis, or at least look in the back seat.
While Lyner from Ar tonelico isn't really at fault for what happened at the start of the game, a special mention should be made about his OVA incarnation. To be more specific: He managed to crash the same ship three times, on the same day.
Halo has numerous scripted crashes. One of them, Cortana assumed the Master Chief did on purpose.
Excluding Foehammer, it seems that the typical Pelican pilot doesn't know how to land without crashing.
Much like the case above with Jojo's Bizarre Adventure, despite not always being the captain, most of the ships that the Chief embarks on within the games end up crashing, exploding, being chopped in half by a collapsing portal, etc. About the only exception is the UNSC Infinity, which is the most powerful ship in the UNSC fleet.
In Knights of the Old Republic 2, Atton manages a total of four crash-landings - twice on Telos, once on Dxun, and once on Malachor V. The first three involved getting shot out of the sky, while in the last case there probably wasn't any way to make a smooth landing on the planet in question.
To his credit, Carth from the first game only crashes the Ebon Hawk once, despite how many times it was shot at.
Ibis Douglas of Super Robot Wars, nicknamed the "shooting star", because just like a shooting star, she inevitably falls to earth...
Reality Ensues in one continuity, as her tendency to crash killed an NPC!
Namely her best friend's fianc?nd rival's older brother. Oh, and whatever confidence she had before goes straight down the tubes because of this.
Maya Amano from Persona 2 crashes every vehicle she commandeers. Including a dirigible. It's something of a running gag.
Kreyg (AKA Hot Blooded Gaming) from Justin TV does this a lot when he plays GTAIV, he even made a company for it!
Grand Theft Auto: San Andreas. Woozie, a very bizarre ally, can drive maginificently. Walking into walls, however, is a frequent occurence. Even More amazing is the fact that he can drive while being blind.
Even more amusing is that his gang acts like he isn't blind at all. It is rather confusing especially since you meet him during a high speed race. Through the countryside. The Crowning Moment of Funny is when he confesses to CJ that he is blind. No shit, homie.
Ratchet & Clank showcases the former of the two protagonists destroying every single starship he pilots in the series, at one point or another.
This even happened to poor Aphelion in A Crack in Time— though, to Ratchet's credit, he tried everything to keep her from crashing, and she gets repaired.
More of a player Captain Crash than anything else, but in Saints Row 2, if the Boss is driving in a car with Johnny Gat and s/he crashes into something, Johnny is liable to muse, "Just like old times."
World of Warcraft: At the end of the Alliance Questline to Twilight Highlands, Fargo Flintlocke says he ditched the landing gear among other things to make the plane lighter - he doesn't "land" usually anyway. Fargo's remark at the end of the trip is a Crowning Moment of Funny.
*Player awakens on a ship and looks up to see the plane burning on top of the mast*
Flintlocke: [his head popping into view, and looking down at the player] What? Like you could have done any better!
There's also a running gag about the Draenei, that any time they're piloting a vehicle they'll crash it. This is likely because their capital, the Exodar, is a magic interstellar space-ship that they note actually Blood Elf saboteurs crashed into Azeroth.
The Draenei arrived on Draenor in a similar fashion. Osha'Gun, the giant diamond mountain in the middle of Nagrand? It's the crashed wreck of their previous ship note Again not their fault, the Naaru piloting the ship darkened (a cycle where a Naaru turns evil for a time) and was unable to retain control.
The hero of Grandia III has designed, built and crashed over a dozen planes before the game even starts. After his personal hero builds him a new plane, he stops crashing. Maybe it was just that he couldn't design a plane that would stay in the air.
James Vega from Mass Effect 3 gets this reputation after he intentionally crashes his shuttle into another shuttle to prevent Dr. Eva from escaping with the plans for the Prothean device. Nobody will let him forget it. He can end up crashing again if he's the one to take over the skycar controls when Shepard abandons the control panel to shoot at Kai Leng during the Citadel coup—although that one is Shepard's fault.
Vega learned from the best. Shepard crashes the skycar no matter who is in the backseat with them. And when chasing Tela Vasir in the last game's DLC missions, Shepard used another skycar to sideswipe her into crashing. And let's not get into allthoseshenanigans with the Mako in the first game. One thing's for sure; if Shepard's driving, something is going to end up in a fiery wreck.
Although he's the best pilot in the Alliance Joker also has a tendency to crash during the finales, although he manages to keep the Normandy salvageable. In Mass Effect 2 it opens with the first Normandy getting shot down with him at the controls. During the finale he also crashes the second Normandy getting you into the Collector Base, but he also gets it up and running again in time for the dramatic escape sequences. In Mass Effect 3 he again crashes the second Normandy during the finale, but is again later able to get her in the air again.
In Dead Space 2 he climbs/gets thrown out of a train, a drilling machine and an escape pod. Outside influences causes the crash in those cases but still, guy climbs out of a lot of wreckage.
Nathan Drake often comes off as this in Uncharted, neatly complementing his status as a Walking Disaster Area, although he has specifically driven only a few. The vehicular victims of his escapades include two planes, a helicopter, two seperate derailments of the same train, two boats (one of them a cruise ship!) and an untold amount of trucks and jeeps. It says a lot when the two most popular games in his franchise depict him in the wreckage of a vehicular accident he's involved in.
Adol Christin of the Ys series doesn't have the best luck with seagoing vessels. He doesn't get into a shipwreck every single time, but it's happened often enough to become something of a running gag.
Launchpad's reputation follows him again in Duck Tales Remastered. He crashes a helicopter off-screen in the Amazon level, and the Himalayas level starts with Scrooge and Launchpad climbing out of the tangled wreckage of their plane. Unsurprisingly, when he needs a pilot to get him to the Moon, Scrooge goes with Gyro instead.
Rast: "I captained my first ship when I was no bigger than my papa's knee... and promptly crashed it into the dock, sinking three vessels with one wreck. It was then I knew, my destiny was to be a sailor."
Tails from the Sonic the Hedgehog series has been crashing planes in almost every Sonic game since his first appearance in Sonic 2. To be fair though, more often than not it's not his fault.
In Spelljammer, landing procedure for tinker gnome-piloted ships involve abandoning the ship, letting it crash safely, then putting the pieces back together. It's not known if any tinker gnome has ever considered developing a safe landing method - although given what they are, if they did there's a good chance it'd be even more disastrous.
Orks in Warhammer 40K. Their aircraft have speedometers reading "stop", "fast", and "WAAAAAGGGGHHHHH!!!", going any slower than the last one (even when landing) is considered cowardice. They also have gears (any but the highest are unused even when "landing"note known to non-Orks as "crashing") and brakes and a clutch (never used).
Ork ground vehicle drivers tend to be less destructive only because they have to decide between being "crazed drivers" and "crazed gunmen" when crewing a tank. Factor in their starship pilots generally being crazed ram addicts, and Orks own this trope.
Launchpad McQuack. Throughout DuckTales, it's a marvel anyone gets in a plane he's piloting. He really is a very accomplished pilot, capable of taking off on any surface, flying through any storm, and weaving through any enemy air space, but he can't land without crashing (One episode even had him celebrate his 100th crash). No doubt he's the only pilot Scrooge could hire for a penny a mile.
It's not just planes - in one episode (after he's crashed a submarine), he pulls out a bingo card from his insurance company with pictures of various land, sea and air vehicles and marks it off. Several other types of craft are already crossed out.
Interestingly, Launchpad may crash all the time, but he's so good at wrecking his planes that he's an expert at crashing safely. This is exploited to save the day in one episode where Scrooge orders Launchpad to pilot a sabotaged blimp that's about to crash on its own. With Launchpad at the control, they still crash, but everybody survives with minor injuries.
By the time of Darkwing Duck, he seemed to have improved (or forced himself to get better because they only had one plane, as opposed to DuckTales' never ending supply). He'd crash occasionally, but that was usually due to getting shot down. There were still a lot of jokes and Shout Outs to his poor landing skills, but on that show it had become more of an Informed Flaw.
Received Shout Outs at least twice on Gargoyles, with the drivers of crashed helicopters musing, "Any landing you can walk away from..."
Ace in the cartoon and comic. Lampshaded in one instance when he says over the radio, "I'm going in!", to which Duke replies, "Every time you say that it gets expensive!"
Cobra troops often joke about their own Air Devil pilots. "What's the last thing to go through an Air Devil's head when he hits the ground? His engine."
Also the notoriously clumsy and oafish Wildcard, who seems to break everything he comes in contact with by random chance except for his vehicle of choice. His filecard says that they put him in that thing because siccing him on the enemy personally is probably against the Geneva Convention.
Fillmore! can be pretty much guaranteed to wreck any ride he gets into, much to Vallejo's frustration.
Batman in The DCAU. IIRC, the Batwing was destroyed in every appearance it made in JL/JLU. It does have landing gear; it lands once in the very first JU episode, although Superman has to catch it and land it for Batman because a wing was shot off.
The pegasus Rainbow Dash exhibits the non-vehicle version of this trope. Dash is a superb flyer; her landings, however, are sometimes far from graceful, as Twilight's library can attest. Taken Up to Eleven when she's afflicted by Poison Joke, which inverts her wings, leaving her crashing into things every few seconds, thrust-vectoring into the floor, and other such mishaps.
A lot of crashing is indicated to come from constantly attempting impossibly difficult stunts in an effort to impress the Wonderbolts. She also has a tendency to lose concentration or get distracted at critical moments (if she starts talking to someone while flying, it's a safe bet she's going to hit something in the next few seconds).
Like owner like pet: Rainbow Dash's pet tortoise Tank, who flies by way of a magically-powered mini-helicopter, is shown constantly crashing into things and people, much to Rainbow Dash's chagrin.
In Star Wars: The Clone Wars, Anakin Skywalker proves the apple didn't fall far from the tree in some ways. He's the finest starfighter pilot in the galaxy... and the worst starfighter lander in the galaxy.
In the tie-in novels, Obi-Wan develops some Captain Crash tendencies, which is lampshaded by Anakin. In three books, he's involved in three separate crashes, although he would (jokingly) protest that he was merely the common denominator rather than the pilot each time.
Due to Continuity Reboot, it may not technically count, but nearly every incarnation of Transformers begins with the Autobots and Decepticons (or Maximals and Predacons) crashing on Earth or recently having done so. Very rare is the Cybertronian ship that has actually landed. Apparently, robots who turn into vehicles are terrible drivers.
For that matter, wouldn't one expect their vehicles to just turn into even gianter robots? Maybe then CAN but they all just keep crashing themselves and dying before we can see any of them transform...
The spaceships that turn into robots also crash frequently. Cosmos seemed to be the worst - almost every appearance in the G1 cartoon had him crashing into something.
The old Rocky and Bullwinkle cartoons featured the world's most incompetent sailor, Captain Peter "Wrongway" Peachfuzz.
Dulcy the dragon in Sonic Sat AM almost always messes up her landings. The only time she doesn't is when she's carrying another dragon's egg.
Invincibility and unlimited strength and power don't prevent Underdog from crashing mid-flight several times per episode. One episode where he drives an armored car shows he doesn't need to be flying to crash, either.
A research team hypothesized that rollerblades are, technically, vehicles. We tested their hypothesis by having Gerald skate into the IRG's headquarters in Tehran. They were right. (This description is a subtitle of a picture showing an exploding building)
When asked if he can land a plane, Grif answers: "That just means stop flying, right?" He is a little better with cars.
Agent Sergio Turbo from the Protectors of the Plot Continuum has been nicknamed "Crash-It Turbo" for his tendency to destroy or at least damage vehicles in some way during missions. To date, he crashed a fighter jet, nearly ran over the whole Department of Sufficiently Advanced Technology while landing another, squished several cars while taxiing an airliner and scraped the hull of a spaceship on the ground while trying to park it... and that's only what happens on-screen. Apparently, he somehow managed to crash a Zodiac inflatable boat too.
This is how Chuck Sonnenberg of SF Debris views Captain Janeway of Star Trek: Voyager, due to a habit of blindly ordering the ship into suicidal situations. One of the ways Sonnenberg views Janeway, at least. Specifically, one of the nicest.
Edward Smith: First he was captain when a ship called the RMS Olympic nearly destroyed a tugboat that was guiding it into dock. Later on, it collided with a British warship. Then Olympic lost a propeller blade and she returned to her builder for emergency repairs. Then he was captain when a ship called the RMS Titanic sailed from Southampton to New York City. Perhaps you have heard about what happened during that voyage.
Not just that, but Olympic and Titanic actually were sister ships (the third sister of the trio is Britannic - originally Gigantic). All three ships experienced some kind of disaster upon their first launch, too (though Olympic managed to avoid getting sunk, and served for many years).
Christopher Columbus crashed his flagships on three of his four voyages to America. On his first voyage, the Santa Maria ran aground and sank off Hispaniola. Second, the Niña ran aground on a small island near Cuba and suffered badly, but remained afloat. On the fourth, two of Columbus's ships were intentionally grounded off Jamaica because of severe storm damage.
He has the excuse of no European In recorded history having been there before...at least the first time. After that this trope was in full force.
Considering the time and effort it takes to accurately chart shoals, shallows, reefs, rocks, and other underwater obstructions, without modern sounding equipment I think you can safely give him a pass on all of them.
Chesley Burnett "Sully" Sullenberger III is a rare good pilot remembered for this. On January 15, 2009, after bird hits took out the engines of his Airbus A320, he calmly landed in the Hudson river - saving the lives of all 155 people on the aircraft. As air traffic controllers panicked and continued to offer him alternate landing places, Captain Sullenberger calmly told them "We'll be in the Hudson". Listen to him here. While this was his only crash, he fits the trope well in this instance and is honorably remembered for it.
Cpt. Hans Ulrich Lutz, Swiss aviator with the Crossair airline, worked as a pilot-in-command and a training pilot, even though his competences were somewhat slim: flying a Saab 340, he failed an upgrade exam to MD-80 eight consecutive times; he crashed an aircraft while sitting on the tarmac (he tried to retract the gear to show the student that it is impossible on the ground due to pressure sensors in the landing gear, but on this particular aircraft, these sensors were temporarily disabled and he simply retracted the gear, resulting in a Saab 340 write-off); once, he almost landed in Italy instead of Switzerland due to navigational errors; and once, he almost flew his aircraft into a lake, confusing it with a runway. Sadly, on 24 November 2001, Crossair Flight 3597 crashed into a hill on final approach due to his major error (he descended well below the minimum safety altitude in heavy snowfall and borderline visibility), claiming 24 of 33 people on board.
Charles Hamilton, an American aviation pioneer and "frequently drunk" stunt pilot, was issued the 12th pilots' license ever...and survived over 60 crashes. Strangely enough, he walked away from most of the wreckage and died of tuberculosis.
John McCain had a longstanding reputation for being unable to stay airborne, pulling stunts like crashing into suburban power lines even though his flight plan was high altitude. It's rumored that his father being in charge of his branch of the armed forces was a factor in his keeping his wings.