Joshua Norton, AKA the "Emperor of these United States and Protector of Mexico" was celebrated in the mid-to-late 1800s as one of these by the people of San Francisco, and is generally considered the patron saint of lovable crazies everywhere. The residents of San Francisco treated "Norton I" as if he really were an Emperor, and some 30,000 people (at a time when San Francisco's population was less than 235,000) attended his funeral. Heck, we have even put him on the Crowning Moment of Awesome page!
So crazy awesome is Emperor Norton that the Discordians (a religion more or less dedicated to becoming more Crazy Awesome) had to create a special category for non-fictional homo-sapiens deserving sainthood ("Saint, Second Class") just so St. Norton could be canonized.
A census taker once tried to question him. He listed his occupation as "Emperor".
He was once arrested in order to commit him to involuntary treatment for a mental disorder. The arrest outraged the citizens and sparked scathing editorials in the newspapers and the police chief eventually released him, reasoning that he may be a wackjob, but he wasn't dangerous, which was more than the chief could say for his peers. Norton granted an "official pardon" to the arresting officer. From that day until his death, the San Francisco police saluted him whenever he passed.
He shows up in fiction on occasion—including a memorable appearance in The Sandman where he gets the better of no lesser a personage than Delirium of the Endless through his unique brand of crazy. "His madness keeps him sane" describes it rather well.
He also appears in the Commodore64 game Neuromancer.
Richard Garriott, the game designer behind the Ultima series. His house is a D&D style castle, he insists on being called 'Lord British', and he's been into space.
The Other Wiki basically confirms this when you read the burglary section. Long story short? Burglar tries to break in. Garriot fires off warning shots from an UZI, while calling the police.
Film director Werner Herzog once ate his own shoe as part of a bet to encourage Errol Morris to finish Gates Of Heaven, a weird documentary on pet cemeteries. He stood down an actor who was shooting at the crew. He pulled Joaquin Phoenix out of a crashed car. His reaction to being shot at by a sniper with an air rifle while he was being interviewed? "It's not a significant bullet."! He also met a principal actor in Strozek while on a roadtrip to dig up Ed Gein's mother's grave. Also, he thinks chickens are the devil.
He once walked from Munich to Paris in the middle of winter, on a whim because he was sure that he could save the life of movie critic Lotte Eisner by doing so. It worked.
His relationship with Klaus Kinski is a mutual example. Herzog met Kinski as a child when Kinski stayed in his family's apartment for three months. Kinski made an impression on young Herzog by doing things like locking himself in the bathroom for two days and smashing all of the fixtures while screaming like a maniac. Years later Herzog hired Kinski to play the lead in Aguirre, the Wrath of God and despite the on-set insanity (at one point Kinski accidentally shot an extra's finger off) he went on to cast him in four more movies. Their intense disagreements and personality clashes resulted in the greatest performances of Kinski's career and Herzog's greatest films.
Lt. Colonel Jack Churchill, who fought in WWII with a longbow and claymore, while carrying his bagpipes. When he was eventually captured, the Germans put him in the Sachsenhausen concentration camp, which he later escaped from. After recapture, Churchill was transferred to another camp. He and the other prisoners were eventually released and Churchill walked something like 90 miles to Italy, where he met up with an American armoured force. When the war was over, he simply expressed disappointment, citing that he could have kept going for 10 years.
He once was on a mission where most of his team had been killed, and only he and six others were left, and an entire battalion of Germans were advancing. The Germans started hammering them with mortars, killing everyone but Churchill. Knowing he had no chance of fighting them and living (and how could he kill more Germans if he was dead?), he instead whipped out his bagpipes and started playing "Will Ye No Come Back Again?"
On the same note, Walter Cowan, 1871-1956. British admiral who first served as a gunboat commander in Queen Victoria's time. He then commanded a battle cruiser in World War One. It is said that he spent his leave in the trenches and cried when the war ended. In WW 2, he helped train the Commandos and was captured in Africa, attacking an Italian tank solely with his revolver. On being repatriated out of mercy, he rejoined and fought again in Italy in 1944.
The Molasses Gang was a gang from New York during the 1870s. They would ask the owner of the shop to fill their hat with molasses (saying it was a bet to see how much would fit). When the hat was full the gangster would shove the hat onto the shop owner and take what they wanted with no resistance. Also Refuge in Audacity, they were able to do it for six years because nobody took them seriously.
Mark Cuban took a desire to follow Indiana Hoosier basketball from Dallas and turned it into a multi-billion dollar internet business. Then he got out of that business just before the bubble burst. Then he lived out every sports fan's dream by buying his favorite team just because he doesn't like how it was being run. Within a couple of years he turned the Dallas Mavericks from the NBA laughingstock to a contender and, eventually, champions. Oh, and he's still willing to act like a die-hard fan in the stands even though the league can fine him for his remarks. Not like any fine they can hand down would matter to a multi-billionaire, after all.
He once remarked that he wouldn't let a particular NBA ref run a Dairy Queen, a major fast food burger/dessert restaurant chain in the U.S. In response, Dairy Queen offered to let him work for them for a day. And he did.
When the documentary on him won an Oscar, he balanced the statue on his chin. A+
Ned Kelly, Irish-Australian bushranger; he and his gang made a last stand against policemen wearing home-made body armour that protected their heads and chests. Kelly reportedly only went down when the policemen shot his unprotected legs, and had twenty-eight gunshot wounds.
He survived that gunfight, only to be sentenced to be hanged. After the judge delivered the sentence, Ned told the judge he'll be seeing him in hell. About 2 weeks after Ned Kelly was hanged the judge died.
If Top Gear is to be believed, Finnish drivers are fucking crazy! (Though, admittedly, crazy by necessity.) Yet that is exactly why they're such good racing drivers.
John "Doc" Holliday was once an ordinary dentist from Georgia. Then he contracted tuberculosis. He headed out west, believing the dry climate would be good for him and, no longer fearing death, became a card player and a gunfighter.
I pity the fool that don't! Not to mention his mohawk! It's PERFECT! It's been proven by science, foo!
About that mohawk? His original idea was to get it in the shape of a T, so that when people asked him his name, he could just point to his hair.
Mr. T once got cancer. What kind of cancer? T-cell lymphoma, of course.
Andre Gregory from My Dinner With Andre. If he was not insane the movie would be just two guys having a meal.
According to Bill Murray, cinematographer Christopher Doyle. He refers to himself as Super Chris, or may be referred to as Sir Christopher. He wears platform shoes while working, and, while living in Hong Kong, he lived across from the world's longest escalator. He would strip naked for all of the escalator riders to see. By the time they got off, they would forget which building he was on. He is also an immensely talented cinematographer who has won awards for his work on numerous American and Hong Kong films.
He was the one who did the cinematography for Zhang Yimou's Hero and every film by Wong Kar Wai, so you now he's just THAT good.
French climber Alain Robert climbs tall buildings as a hobby, including most of the world's tallest high rises. Without any safety whatsoever. He's regularly arrested as a result of his antics. The most incredible thing is that the man suffers from permanent vertigo. A condition he got as a teenager, by falling from a height of 15 meters and surviving. Twice in the same year.
Skippy, of Skippy's List: The 213 things Skippy is no longer allowed to do in the U.S. Army.
48. I may not use public masturbation as a tool to demonstrate a flaw in a command decision.
58. The following words and phrases may not be used in a cadence—Budding sexuality, necrophilia, I hate everyone in this formation and wish they were dead, sexual lubrication, black earth mother, all Marines are latent homosexuals, Tantric yoga, Gotterdammerung, Korean hooker, Eskimo Nell, we've all got jackboots now, slut puppy, or any references to squid.
72. May not wear gimp mask while on duty.
100. Claymore mines are not filled with yummy candy, and it is wrong to tell new soldiers that they are.
One of Skippy's friends gives this really important piece of advice.
Never tell a military pilot “There’s not enough room to fly under that!“, unless you want him to try.
The King of Bling! The Ayatollah of RocknRolla! The Man of 1004 Holds! Y2J! Chris Jericho!!!
For clarification on how crazy awesome the man is, go to his other Wiki page, and try to read the whole thing. You'll be exhausted before you finish the wrestling section, let alone his music, acting, writing, hosting, etc., etc., etc. Either he never sleeps or he's figured out a way to have 36 hours in a day.
Sir Ranulph Fiennes. Highlights of his life include his expulsion from the SAS because he blew up a dam in a Wiltshire village as a protest against 20th Century Fox, hacking off his own frostbitten fingers with a power tool, forgetting his own frostbitten toe and leaving it beside his bathtub when it came off, discovering the motherfuckinglost city of Ubar, and reaching the peak of Everest in his sixties, but perhaps the best has to be running 7 marathons, in 7 days, on 7 continents, only a few months after a heart attack and bypass operation—and, with doctor's orders not to let his heart go over 130 beats per minute, he forgot his heart monitor.
Wesley Willis. Was diagnosed as paranoid schizophrenic, and wrote some truly inspired songs, such as "Birdman Kicked My Ass", "Kill That Jerk", and "Rock & Roll McDonalds".
Larry Williams is either this or a Bunny-Ears Lawyer. He did things like pimp out prostitutes, deal drugs, and convince Little Richard to go into priesthood by waving a loaded handgun in his face, but he was one of the coolest Band Managers Ever. He died in the eighties, from "Suicide", but he is still revered as a legend.
French composer Erik Satie (d. 1925), whose works for piano include titles such as: Gnossiennes, Gymnopedies, Three Pear-shaped Pieces and Dressed As A Horse, and who collected umbrellas and pianos in his tiny, one-room apartment, where he never let anyone else in.
He also composed a piece called Vexations. Consisting of two bars of music with instruction to repeat it 840 times, it takes around 24 hours to perform. At least one pianist attempting a solo performance started panicking and hallucinating before quitting:
I would not play this piece again. I felt each repetition slowly wearing my mind away. I had to stop. If I hadn't stopped I'd be a very different person today... People who play it do so at their own great peril. ... [I] had to stop because [my] mind became full of evil thoughts, animals and "things" started peering out at [me] from the score.
Evidently Satie was, constitutionally, an austere minimalist:
I eat only white foods: eggs, sugar, grated bones, the fat of dead animals; veal, salt, coconut, chicken cooked in white water; fruit mold, rice, turnips; camphorated sausage, dough, cheese (white), cotton salad, and certain fish (skinless).
Steve Irwin. He constantly got a bit too close to snakes, crocodiles, sharks and many other dangerous animals almost on a daily basis, and not only wasn't afraid about doing it, he was more excited than a five-year-old.
Joe Davis. Part scientist, part avant-garde artist. To quote a Cracked article featuring him: "He has a map of the Milky Way broken down into a series of base DNA pairs, and is coding it into transgenic lab-mice. He insists on landing microbes like Marlin... because he considers it "only sporting". In protest of what he viewed as censorship, Davis beamed his own, female-friendly version of the famous Arecibo Message toward a distant star cluster. He stuck microphones inside the vaginas of the entire Boston Ballet, and shot the sound of them contracting into space." Just to give Carl Sagan the finger!!! He also is building "a memorial for hurricane victims that happens to be a 10-story tall tower in Mississippi that harnesses the excess electrical nitrogen in the air brought on by lightning storms and fires it back into the storm in the form of a giant laser."
The laser does nothing, incidentally. He just wanted to shoot a laser at storms.
The Chinese Cavalry of 1967. Shooting when riding horses is okay for any cowboy, but how about firing AK and RPD Machineguns? When charging a MUSHROOM CLOUD? Go watch the last minutes of Trinity and Beyond: The Atomic Bomb Movie. It's filmed by those cavalrymen themselves.
Admiral Hyman Rickover, father of the nuclear Navy. Well known for making candidates endure such crazy trials as conducting interviews in total darkness, trying to balance on a chair with one of its legs shortened, and berating them for anything short of an A in technical courses. Then, there was this one time when the Senate called him in to testify because they were concerned about the safety of Naval nuclear power, which he personally demonstrated by drinking a glass of a reactor's primary coolant on the floor of the US Senate.
One story is of him interviewing a potential Nuc officer by taking him to lunch, then telling him to leave about ten seconds after the food arrived. Why? Because the guy reached for the salt shaker before tasting his food to verify it need salt.
To this day, Rickover remains the record-holder for longest time spent on active duty in the US military: over 60 years. And that "father of the nuclear Navy" bit? He did most of the work himself, while Obstructive Bureaucrat after Obstructive Bureaucrat stood in his way. As a boy, he quit his job in order to go talk to politicians and wound up going to the Naval Academy because of it, and thenceforth never let "rules" stand in his way.
Some guy in Florida caught a shark on a fishing line while surfing (why he had a fishing line while surfing is anyone's guess) and allowed it to pull him along for half a minute before the line snapped.
Chef Jose Andres, molecular gastronomist (think Mad Scientist/Mad Artist chef), known for deconstructing food such as the "blasphemous" clam chowder (all the ingredients are more or less whole and separate, and the potato chowder is actually a foam).
Relating to the above clam chowder, Ivar Haglund, a Seattle businessman, was unquestionably out of his damn mind and very successful at it. He parlayed a third-rate aquarium into a wildly successful chain of restaurants, owned one of the local TV stations (and took advantage of that fact to give himself a show singing Norwegian folk songs for an hour each week), and bought the Smith Tower (at one point, the tallest building west of the Mississippi River). When the Seattle Building Department took issue with a salmon-shaped windsock he flew from the tower's flagpole, he sent them several protest letters in the form of pun-loaded poetry. His publicity stunts were legendary; having a wrestling match between a retired boxer and an octopus, putting a baby harbor seal in a baby carriage and taking it to see Santa, taking advantage when a train car full of syrup sprung a leak in front of his restaurant by racing out with pancakes, encouraging his patrons to feed the seagulls, running for office and getting elected as a joke, and peppering his advertisements with a Hurricane of Puns. He died very wealthy, and the chain of restaurants bearing his name is still thriving.
He died after his army had taken a castle, but hadn't yet cleared it. He decided to tour the castle walls without wearing chainmail, and when he saw a 13 year old boy shooting arrows at him, he applauded the kid's spirit. Then one of the arrows hit him, the wound got infected and on his deathbed he ordered the kid to be brought to him so he could forgive him and give him a reward for valor.
He got it from his mom, Eleanor of Aquitaine. She was more Awesome than Crazy, and a side order of Refuge in Audacity when you consider women had no legal standing in the era. Insisted on joining her first husband on a Crusade tour, marched with the vanguard, and argued for a plan that would have caught the Muslim army off-guard, possibly winning the Second Crusade. (Louis ended up throwing her in prison instead and got his ass handed to him with his bad tactics) She brought the beginnings of Admiralty Law with her to France and England, and actively helped (and/or encouraged) her sons' revolt against her husband, leading to another period of house arrest. She ruled England as regent when her son was off Crusading, and personally traveled to Germany to bail him out when he was captured. And, called out The Pope himself when she thought he was not acting with enough urgence to aid in securing Richard's release! And did NOT get excommunicated for that.
Charlie Wilson, of Charlie Wilson's War fame, is practically the embodiment of this trope. The filmmakers intentionally left some of the craziest things he did out of the movie because audiences didn't believe it.
Milton H. Erickson. Check the stories about how he told a woman who felt ill about her in-laws' visits to vomit in their presence and cured a man of his fear of elevators by instead making him scared of the operator girl kissing him. Oh, and then there's the part about where he survived polio because he overheard the doctors telling his mom he'd be dead by morning and inadvertently hypnotized himself into surviving by focusing on the sunset (what he at the time believed to be his last).
Camillo Benso, conte di Cavour, the Italian Bismarck, had a penchant for holding diplomatic negotiations in airless rooms with either no windows or ones that could not be opened. With the temperature always slightly too warm. After having eaten/while eating garlicky food (or sometimes just plain garlic). And he was physically quite intimidating. The result? He typically got what he wanted in these negotiations, and got it rather quickly.
Phil Spector. While unquestionably a lunatic, as the many friends and prostitutes whom he shot at will attest to, he is rightfully a legend as a music producer and songwriter. Any Phil Spector story, from someone who knows, will be attached to a comment about how he changed music.
Werner Forssman- A medical student who wanted to learn more about the heart, but decided the usual method, dissection of specimen from a corpse, wasn't enough. No, he decided he was going to study a living heart by jamming two feet of cable into a person's circulatory system. The Crazy Awesome part? He used his own.
Roosevelt "facts" that he inspired predate "Chuck Norris Facts" by quite a long way, as this quote from his eulogy makes clear:
"Death had to take him sleeping, for if Roosevelt had been awake there would have been a fight."
2nd Lt. Audie Murphy is the most decorated American soldier of WWII and the epitome of crazy awesome! Just read his Medal of Honor citation:
2d Lt. Murphy commanded Company B, which was attacked by 6 tanks and waves of infantry. 2d Lt. Murphy ordered his men to withdraw to prepared positions in a woods, while he remained forward at his command post and continued to give fire directions to the artillery by telephone. Behind him, to his right, 1 of our tank destroyers received a direct hit and began to burn. Its crew withdrew to the woods. 2d Lt. Murphy continued to direct artillery fire which killed large numbers of the advancing enemy infantry. With the enemy tanks abreast of his position, 2d Lt. Murphy climbed on the burning tank destroyer, which was in danger of blowing up at any moment, and employed its .50 caliber machine gun against the enemy. He was alone and exposed to German fire from 3 sides, but his deadly fire killed dozens of Germans and caused their infantry attack to waver. The enemy tanks, losing infantry support, began to fall back. For an hour the Germans tried every available weapon to eliminate 2d Lt. Murphy, but he continued to hold his position and wiped out a squad which was trying to creep up unnoticed on his right flank. Germans reached as close as 10 yards, only to be mowed down by his fire. He received a leg wound, but ignored it and continued the single-handed fight until his ammunition was exhausted. He then made his way to his company, refused medical attention, and organized the company in a counterattack which forced the Germans to withdraw. His directing of artillery fire wiped out many of the enemy; he killed or wounded about 50. 2d Lt. Murphy's indomitable courage and his refusal to give an inch of ground saved his company from possible encirclement and destruction, and enabled it to hold the woods which had been the enemy's objective.
He also bit his co-star, Karen Gillan, to get Enforced Method Acting, and the reason Steven Moffat had to kill The Fez was he feared Matt Smith would insist it become part of the Doctor's outfit... and wear it all the time out of character too. Matt Smith seems as Crazy Awesome as the Doctor he plays.
This anecdote about by Steven Moffat sums up just how much of his physicality as the Doctor is just him.
That first anecdote gets funnier when you learn that Matt Smith was a torch-bearer for the 2012 Olympic Games.
Troy Hurtubise: Inventor, Canadian, and lunatic. He invested two decades and tens of thousands of dollars developing the Trojan armor to protect coalition soldiers (such as his own brother) from I.E.D.s. The Trojan is based on armor he developed for fighting bears, with input in equal amounts from real-life soldiers and the HALO games. He bankrupted himself developing it, and has thus far failed to attract the interest of any government. Yet in live fire tests, the Trojan has been strapped to a lump of wet clay, taken multiple rounds at point-blank range from a 9mm pistol, a .357, and a 12-gauge shotgun, without so much as a dent in the clay underneath (which he then demonstrated was soft enough for his finger to gouge a fissure into). Just in case there's still doubt as to whether or not he's worthy of the Crazy Awesome tag, it should be noted that the Trojan armor includes a solar-powered air-conditioned helmet.
In order to test another one of his inventions, the heat-resistant clay he calls "fire paste," Hurtubise smeared it on his own face, let it dry, and then aimed a blowtorch at it. For ten minutes.
He claims to have developed a device which can make solid objects, like walls, stealth shielding, and HIS OWN HAND transparent. It also fries electronic devices and kills goldfish.
Melvyn Foster. He was a cabby that was accused of being the Green River Killer. However, he was trying to protect the prostitutes and runaways from people like Gary Ridgeway. He spent time in prison for other crimes and this lead to his conversion of him trying to protect those less fortunate than himself. He was sort of Jesus with a really bad temper.
Lieutenant General Henry "Gunfighter" Emerson was undoubtedly eccentric and his activities somewhat questionable by conventional thinking (he tried to make new sports out of basketball or soccer by fielding battalions or brigades instead of just a standard team, and this was just of many examples). But he was dedicated to the morale and welfare of his soldiers, and by all accounts he did an excellent (if eyebrow raising) job at making his soldiers feel like they could take on the world.
Butch O'Hare. Granted, the guy was Irish, so it comes with the territory, but anyone who takes on eight enemy fighter planes single handed has got to be worth mentioning here. (Technically, he was supposed to have backup, but his wingman's guns jammed.) First US Navy Ace of WWII. And that airport in The Windy City? Totally named after him.
Dragonflies, roses, lightning, and a viking helmet? Admit it: you wish you were invited to this reception.
Joan of Arc managed to convince a group of dispirited French soldiers, and the king of France, that the visions she'd been recieving since 12 weren't something they burned you as a possessed person for in those days, but in fact were the real deal, and she proceeded to live up to the hype by kicking the English out of half of France, leading the final charge at Orleans with an arrow in the neck. And she did this while being a sworn pacifist. She carried the banner into battle instead, one of the most dangerous jobs on the field as you literally have a flag over your head screaming "shoot me please!" Even when captured she managed to stave off heresy accusations despite being an illiterate peasant faced with cutthroat clergy with enough trick questions to fill a test paper. She was eventually put on trial for political reasons. She was put to death for heresy, having worn mens clothes, despite numerous officials at the time agreeing that her reasons for doing so were valid.
John Brown◊ the abolitionist. Favored a type of rifle known as the Bible, and split five slaveholders' heads open with a BROADSWORD. When he was caught and had to be put to death by the North, he quietly told his captors that all he wanted to do was help those who couldn't be helped and if he had to be put to death, then so be it.
Frank Frakking Zappa. Moon Unit, Dweezil, Ahmet Rodan, Diva. Watch Out Where The Huskies Go And Don't You Eat That Yellow Snow. Billy the Mountain. Magdalena. Poofter's Froth Wyoming Plans Ahead. We're Only In It For The Money. Frank Zappa And The Mothers Of Prevention. Ship Arriving Too Late To Save a Drowning Witch. Lumpy Gravy. Brown Shoes Don't Make It. Absolutely Free. And before anything else, he was noted for a phone conversation with Edgar Varese while still a teen, and serving ten days in jail (before he became famous) for producing an "obscene" audio recording—an experience for which he never forgave the Los Angeles Police Department. And yet, dying of cancer, he managed to come across as almost saintly. He is missed. God almighty, he is missed.
Andrew Hussie puts an insane amount of work into Homestuck, purely for the art. Considering that Homestuck itself is more or less Crazy Awesome: The Series, not to mention what Hussie's earlier work is like, it makes one wonder...
From the memoir Tokyo Vice by Jake Adelstein, it mentions that one group of thieves in Japan used little stickers of smiley faces and Hello Kitty to cover up the holes they drilled in a wall when doing a job so no one would no anything was amiss.
Adelstein himself could be considered an example of this trope, since he's a Jewish-American journalist that resides in Tokyo, works for a Japanese newspaper, and wrote the biggest exposé in recent history on the Yakuza and is still very much alive!
Adrian Carton de Wiart. Just... Adrian Carton de Wiart. If you read up on his involvement in the Boer War and both World Wars, you'd see how one man could define "crazy awesome". To put short and simple, this British soldier received many injuries in various battles, including a missing left eye (resulting in a badass eyepatch) and left arm. It was reported that he once bit one of his own finger off when doctors where unable to decide whether or not to amputate it. Even his capture by Italian soldiers during WWII shows some badassery, seeing how he swam a mile to the Italian shore after his plane was shot down one mile from shore, despite of being in his sixties and missing an arm. He even once stated that a battle during the Boer War (in which he lost his eye) was "exhilarating fun". And this is only scratching the surface of his crazy awesomeness.
After fighting in three wars, losing half a dozen bodyparts, crashing airplanes in the ocean and charging trenches his entire life, the title of his autobiography? Happy Odyssey.
General Henry Knox, chief artillery officer for George Washington during the American Revolution. A rather overweight, out-of-shape, twenty five-year-old book-binder and -seller, he was an avid devotee of military history who had never, prior to joining the Colonial army in 1775, experienced a day in military service. A self-taught soldier, Knox rose to become one of Washington's right-hand men, and was considered by his enemies, the British, to be an outright genius when it came to the use of artillery. Fort Knox is named in his honor.
Anne Smith Strong, a farmer's wife in New York during the American Revolutionary War, was a key intelligence agent working for George Washington against the British. She came up with a novel and completely unsuspected method of passing intelligence on British troop movements to Washington based on her laundry: the specific order she hung the pants, shirts, and bedclothes, combined with the colors of said items, determined the content of the messages. Washington would later say that her genius at coming up with a code no one would ever think to look for was one of the reasons the Americans won the war.
Edward Teach, better known as the pirate Blackbeard. He put smoldering coals in hs beard just to scare the living hell out of people. The man took 20 slashes, 4-6 gunshot wounds, and a decapitation to finally die, and when he did it's said his headless body started swimming circles around the ship.
There's a story that says he once shot his first mate in the knee completely at random. When asked why, he said "If I don't kill a man every so often you forget who I am".
Timothy Dexter. Made a series of guaranteed-to-lose business deals (e.g shipping cold-weather gear to the Caribbean) and made a profit on all of them. Jealous rivals encouraged him to ship coals to Newcastle, a proverbially absurd trade, and he did - the coals arrived during a coal miners' strike and he made a substantial profit on the deal. On the strength of this, he wrote his memoirs, entitled a pickle For the Knowing ones: the original edition contained no punctuation whatsoever, and when some readers complained he published another edition that an entire page of punctuation marks and a note that readers should "peper and solt it as they plese."note Dexter's spelling was rather more crazy than awesome.
Lieutenant General Chesty Puller is one of, if not the, most decorated combat Marine in US Marine Corps history. He is the only Marine to be awarded five Navy Crosses (the second highest award for valor they give out, for extraordinary heroism in combat). Yes, that's right. In a military division already known for their badassitude, he managed to distinguish himself for valor five separate times.
Upon being shown a flamethrower for the first time, he is reported to have asked where the bayonet was supposed to go.
Sources vary as to the exact quote, but at the Battle of Chosin Reservoir, when he was informed that he was surrounded by 67,000 Chinese troops, he said some variation of "We're surrounded. That simplifies the problem." It takes a special brand of Crazy Awesome to decide that being surrounded and outnumbered more than two-to-one is a good thing. It takes an even more rarified brand of crazy awesome to then win the battle.
On an inspection tour, he once demanded to be taken to the brig so that he could meet the "real Marines."
English football player Terry Butcher got wounded during the World Championship qualifier in Sweden 1989. He got a nasty cut in the head, but stitches and bandages didn't stop him from keeping playing. He bled throughout the game until his white shirt turned red.
George Patton had a tank named after him and popular myth holds that he spent some time in the war shooting down enemy aircraft with his trademark ivory handled revolver.
Though it is accepted that this tale is apocryphal, it should be noted that it's generally agreed that it is the sort of thing that Patton might have done. The general went far out of his way to appear larger-than-life to inspire his troops.
The Allies actually managed to weaponize this image in the prelude to Operation Overlord. Relying in part on Patton's trademark image and bluster—along with decoy trucks and tanks—to bluff the Axis into believing that the Allies were going to land at Calais rather than their actual target, Normandy. After all, a man like Patton would obviously be leading the cross-channel invasion, right? The Nazis certainly thought so.
Hunter S. Thompson: Gonzo Journalism simply wouldn't have existed if not his willingness to do bizarre—even insane—things to himself and occasionally others. This mostly meant drugs, but it also meant things like going around in a bar waving a cattle prod and yelling at people to get out of his way.
Italy's infamous Gabriele D'Annunzio, with emphasis on the crazy. On the crazy side, he had his lower ribs removed to be able to use his mouth when having A Date with Rosie Palms (among his many antics). On the awesome side, his record during World War I: he charged at an Austro-Hungarian trench line while wearing a Badass Cape and with a revolver in each hand (yes, Italian military issue revolvers of the era were underpowered, but he remained the only one to actually do it) and a combat knife in his mouth, in the Backar's Mockery he took two speedboats with torpedoes strapped on them in the most well-defended harbour of the Austro-Hungarian Empire, fired torpedoes at the moored ships (that survived only because the Austro-Hungarian admiralty had placed torpedo nets everywhere just in case) and left mocking messages in bottles, and when the Austro-Hungarians carried a demonstrative bombing raid on Milan he personally led a raid on Vienna and dropped propaganda leaflets (a quarter with a poetic message written by D'Annunzio itself that was considered a war crime and so wasn't translated, and the others with a more understandable message that could be resumed in "You've lost the war, you're fighting against the whole world, surrender while you still can and before we change our minds and return with bombs") to prove that they could bomb the Austrian capital itself but were too civilized to actually do it.
The Bersaglieri, the elite shock infantry of the Italian army. On the crazy part, they don't walk but run all the time, even when playing brass instruments (and their marching band includes only brass instruments), and were originally created to countercharge against enemy cavalry. On the awesome part, during the Battle of the Chernaya they did countercharge Russian cavalry, and routed it, something that the Zuaves (at the time considered the most Badass infantry of the world) had just considered impossible (and prompting the Zuaves to admit the Bersaglieri were more awesome than themselves and gift them their fez as secondary headgear). Oh, and the Bersaglieri were tired because they had just feasted the previous day.
Still on the awesomeness, Erwin Rommel has admitted that any German soldier was inferior to the Bersaglieri, and in Africa (where he commanded both Italian and German troops) had the habit of throwing them at positions he could not attack with the usual mix of tanks and infantry and then wait for the enemy to run away in holy terror.
Admiral Charles "Swede" Momsen of the United States Navy was a decorated combat officer who commanded submarines and the battleship USS South Dakota with distinction during the Second World War. His contributions to science, medicine, and deep-sea rescue, however, made him Crazy Awesome:
While studying decompression sickness for the Navy, Momsen devised the first mixed-gas diving rigs (in this case, oxygen/helium) and through trial-and-error, developed the first protocols for safe mixed-gas diving. That's awesome enough, but the crazy part came from testing the mixtures on himself. He methodically and repeatedly gave himself the bends to research ways to avoid getting the bends.
In 1939, he rescued the survivors of a disabled submarine, the USS Squalus. Rescuing 33 sailors trapped 70 meters below the surface is amazing enough, but that could have never happened without two critical pieces of equipment: the diving rescue bell, and the Submarine Escape Lung (an early rebreather); both of which Momsen, himself, invented.
He also, incidentally, recovered the submarine, itself; which was repaired, renamed Sailfish, and went on to fight in the Pacific during World War II.
In 1943, the Navy was having problems with the Mark 14 torpedo, which would often fail to explode when it impacted a ship's hull. The Navy turned to then-Admiral Swede Momsen to lead an investigation into the defective torpedoes. Momen did so by live-firing armed torpedoes at targets, and then he personally dove in to recover the unexploded ones so experts could take them apart and figure out where the problem was. This bears repeting: as a flag officer, Momsen dove into the water to recover torpedoes with armed, high-explosive warheads that he was fully aware were equipped with defective fuzes.