World of Warcraft has its share of Crazy Awesome characters scattered around the worldspace, but the grand daddies of all things both awesome and completely batshit crazy are: the entire goblin race. To wit, Azeroth's goblins are your run-of-the-mill green midgets hopped up on intelligence-boosting kaja'mite which turns them into a race of Mad Scientists. They put that mad science to work being Azeroth's premiere hustlers, con-artists and extortionists, as well as being the reigning kings of stuff which blows up as well as some of the wildest inventions you could possibly imagine; shark-shaped submarineswith head-mounted laser cannons are just the tip of the iceberg with these guys.
You can find a fair few topics asking why the Cenarion Circle, or the Earthen ring hasn't decided to turn on any of the goblin franchises because of the repeated, guiltless, and blatant environmental damage assosciated with the entire race. The simple truth is, They can't. The economy on Azeroth is controlled by said goblins. If they were challenged, it would ruin the worldwide economy.
And this is assuming the combined might of both Horde And Alliance could withstand the sheer number of resources the goblins could level at them.
What is a Worgen rogue fighting a Forsaken rogue besides a tophat-wearing werewolf-zombie knifefight? Why, it's apparently rather awesome.
One of the bosses, Biggy Man from Splatterhouse. Possibly because he has CHAINSAWS where his hands should be.
Once again, The Joker, with special mention to Batman: Arkham Asylum. Ridiculous thematic weapons? Check. Sauntering, acrobatic brawl maneuvers? Check. Bomb threats to keep the GCPD from entering? Check. Finding out said bombs consisting of marzipan and kittens? Check.
Not to mention that one of his newer tactics, Jarate, involves attacking people by throwing the contents of his jars on them. Now what would a sniper who spends days at a time holed up in his perch keep in a jar? That happens to also be a yellow liquid?
Some of the background characters, too. Saxton Hale (head of Mann Co—"We sell products and get in fights") in particular. One letter from him that has been seen out there can be, depending on which boxes are ticked, either "thank you for your submitted product idea, we'll get back to you" or "you bastard, you tried to steal from me, I'm going to hunt you down and beat you to death with my own bare hands."
Heavy: Doktor! Are you sure dis will work?! Medic: HAH! I HAFF NO IDEA!
The Heavy deserves an special mention for having a WORKING finger gun.
Currently theirs don't take Violation of Common Sense as the exception but the norm. This means they have inane ideas such as using a neon light underwater, punching people with mitts in a fight to the death, beating people to death with a fish, death by icicle, hacking your own arm of just for a prosthetic you had no need for in the first place, shooting people with a crossbow to heal them, above mention grenades and "Yellow Liquid" weapons and that hand grenade club, a rocket launcher, flamethrower and Heal-Gun thingy made from random household items, holding bear claws over your hands in a fight, and we're just grazing the list.
Destroyman: A dirtbag mailman that cosplays as a superhero that convinces Travis to turn his back on him, get zapped by his joy buzzer to the brink of death, has machine guns in his nipples, and a laser codpiece. And he likes announcing his attacks.
He's not cosplaying. He's actually the star and producer of the independent Destroyman films. And calling attacks actually activates his SFX converter, which is the device that launches his attacks.
Harvey Moseiwitsch Volodarskii: He's a stage magician, for starters. A stage magician that you fight in the middle of a live performance, while he summons pigeons to attack you, flips the screen upside-down (not that it helps him much) and getting out of his instant-death attack involves a Houdini-esque escape trick.
Speed Buster: A deaf little old lady with a shopping cart... that turns into a (roughly) fifty-foot long Wave Motion Gun. And her BGM is called "Mach 13 Elephant Explosion".
Bad Girl: In her spare time she chugs beer and beats gimps in S&M get-up with a baseball bat...in a lolita getup. She'll also spit booze on to the bat to light it on fire halfway through the fight. Be careful when she goes down.
Dark Star: Giant Dragon Beam Katana, for starters. Story-wise and metafictionally speaking, the only reason he exists is to set the player up for a Mind Screw as he, by revealing his face, convinces Travis that he's his killed-in-front-of-Travis'-eyes-dead father... only he's not, which ought to qualify for something—if not crazy-awesomeness then a defining moment in Suda51-ism.
From the sequel: Skelter Helter: Has a fairly bizzarre gun, but other than that, is fairly unremarkable... until a few minutes after his decapitation, he tells Travis he's not done with him, then raves on about how killing someone isn't the same as ending their life.
Charlie MacDonald: Not only is he an assassin, but so's his harem of twenty-four cheerleaders, and apparently their collective modus opperandi is summoning a Humongous Mecha from space (or they transform into said Mecha, either way is awesome).
The demon Glottis from Grim Fandango has a mindbogglingly huge enthusiasm for driving really fast. So when Manny Calavera, an unsuccessful Reaper and the game's protagonist, is in need of a driver to take him to the Land of the Living after his rival gave his usual driver the day off, he desperately persuades Glottis to become his new driver. Glottis begins his career as a driver by sending Manny to get the boss' approval to make "slight alterations" to Manny's company car. It all goes downhill from there.Beholdtheawesome.
Francis York Morgan from Deadly Premonition. He talks to his imaginary friend all the time, in full view of everyone, and launches into monologues about old movies and horrific past cases he was on even if they only loosely connect to the subject at hand.
Sheogorath! How, you ask? Well, his quests in Morrowind and Oblivion respectively involve killing a giant floating cattle-like jellyfish with a cursed fork and fulfilling a prophecy involving stinky cheese and burning dog corpses raining from the sky.
"I once dug a pit and filled it with clouds... or was it clowns... come to think of it, it began to smell... must have been clowns. Clouds don't smell, they taste of butter. And tears." "Time for a celebration! Cheese for everyone! Wait, scratch that, cheese for no one. That can be just as much of a celebration, if you don't like cheese. True?" "I'm so happy, I could rip out your intestines and strangle you with them!"
In The Shivering Isles, attacking him causes him to paralyse the player, before teleporting them about a thousand feet over the island. If you can actually find the area he teleported you to, you find a man who was similarly executed... for the great crime of having a moustache. Of course, this is the realm of a Mad God.
Sheogarath also fulfills this trope in a somewhat more literal way, what with being the God of Madness and all—the less crazy he is, the less powerful he is! He also inspires this trope in his followers, sometimes.
Cicero in The Elder Scrolls V: Skyrim doubles as this and Creepy Awesome. Despite dressing as a jester and coming across as nuttier than Sheogorath, his insanity belies the fact that he's a highly skilled assassin of the Dark Brotherhood.
Albert Wesker, from the Resident Evil series, is a perfect example of this trope: his master plan involved getting stabbed through the chest (by a Tyrant's large, clawed hand, no less) so that an experimental virus he injected into himself would reanimate him, with glowing red, cat-like eyes, superhuman strength and speed. It sure as all living hell worked.
Come Resident Evil 6...In Chris' campaign, his partner Piers gets infected with the C-Virus during the final boss fight. Infected he may be, Piers jumps into the fray, complete with mutated arm, and helps Chris out by shooting friggin' lightning at the boss. Hell. Yes.
Drei from Phantom of Inferno starts off as a sweet, somewhat bratty little girl but the Not as You Know Them after the timeskip is made of this. Stepping out in front of big gangsters and daring them to shoot her, sniping items off the belts of her targets from atop a motorcycle, walking down the streets of Tokyo in a rage and trying to pick fights with random youths despite not knowing a word of Japanese, having sex with the main character in the middle of a gunfight...
Disgaea 3: Absence of Justice: Princess Sapphire Rhodonite is gloriously off her nut, and that's why we love her. Take her idea for "opening up Mao's heart," for example...
Kefka, the main villain of Final Fantasy VI, manages to be both an Laughably Evil source of humor and a genuinely threatening (or outright scary) Monster Clown by the virtue of being Crazy Awesome. To bully around a foreign leader, he sets a whole castle on fire and quips about having started a barbeque.
Dissidia: Final Fantasy actually lets Kefka speak, and if anything, he's even more Crazy Awesome in the cutscenes. In addition, he subscribes to the Confusion Fu school of fighting—his fighting style revolves around wacky, unpredictable spells that zig-zag through the air, home in on the opponent, or hit around the opponent to catch them on the dodge. In essence, his entire fighting style is that he's Crazy Awesome - if he used normal spells, his entire gimmick would go out the window.
And then there's Gilgamesh, the Ensemble Dark Horse who has managed to cross the Final Fantasy multiverse on a search for rare swords. Amazingly hammy, boisterous and absurd, he manages to combine being badass and cool with being a complete moron. Dissidia's prequel gives him attacks reflective of this—Missile fires a giant homing missile that he pulls from Hammerspace, Rocket Punch has him launch a pair of giant boxing gloves at opponents, and his Jump attack has him leap into the air and descend to deliver a diving headbutt. And if he misses, he crashes into the ground head-first and has to pull himself out.
In The Sims 3, you can give your Sims the "Insane" trait, which lets them to do all sorts of hilariously ridiculous things, like fishing in swimming pools (and actually catching fish this way!).
Similarly, the "Neurotic" sims get compulsive, yet easily fulfilled wishes (like checking the oven) which put them in a positive mood, and have access to a special "Freak Out" command which puts them in a "happy place" mentally that means that for several hours, their Fun need meter won't degenerate no matter what kind of stresses they're subjected to. Quite a powerful ability in the Sims universe!
Adventure Mode takes it Up to Eleven...even the rules are Crazy Awesome, such as armour-piercing throwing sand and the use of entire skeletons as melee weapons.
The following lines are all taken from the Bay 12 forums. Context can sometimes be inferred, but is rarely necessary.
"I like the fact that we are seriously discussing how to drop dwarfs off towers using kittens as cushions." "I would fill it with magma if there was any on my map; there isn't, so I'm filling it with rhesus macaques." "Apparently having a redundant creature entry causes the game to say "Oh look, it's crazy world now. Nothing makes sense! Alligators live in houses!" "Exactly, except that instead of watering lawns, it's destroying ecosystems!" "To this day, I'm not sure how a grizzly bear manages to sneak into the fort and steal my beer." "Odd how 'experiment' in DF is often synonymous with 'raging inferno of death and despair'." "And now the thread is about starfish porn." "Only geologists and Dwarf Fortress players get this excited about pictures of rocks. Although for geologists it's professional, wheareas for Dwarf Fortress players it's more like porn." "Personality-wise, dragons are nothing more than giant, scaly, fire-breathing cats." "If in doubt, magma." "The Pointless Tower is progressing according to plan, which is impressive since I don't have a plan for it." "I have a 'drunk fort', which I only work on when significantly under the influence. I checked it out one time when sober, and couldn't make head or tails of what the flip was going on." "The best part of the thermonuclear catsplosionnote a minor mod that raises a cat's body temperature to that of the surface of the sun is that they don't explode if they're in a cage...you know what I'm thinking. Place cages throughout the map, link them to levers...you now have cat-mines." "[...]of course, I could never have predicted that duplicating a creature entry would result in boiling silk that freezes people to death. Go figure." "Such is life. Sometimes you succeed in your goals and sometimes you and everyone around you is murdered by a gigantic spider." "I even had a dwarf woman marry a male livestock dwarf, then milk him, then butcher him, and cook his meat along with his milk." "You have proven yourself to be a real dwarf, by nuking hell with cats, impaling demons with ballista arrows and crushing them catapults. Armok would be proud." "But lo and behold! Flat worm clownnote "clown" being the Unusual Euphemism for The Legions of Hell corpses! My prodigious butcher shop gets to work and pretty soon I find myself the proud owner of 118 globs of flat worm clown tallow. I'm currently waiting for it to be rendered, but the solution is obvious: I need to make me some flat worm clown soap." "But wouldn't poison squirrel demon soap dissolve the flesh of anyone who uses it? I THINK WE HAVE OUR NEXT EXPORT TO THE ELVEN KINGDOMS, GENTLEMEN!" "Now all you need to do is wield 300 shields and 300 spears and then singlehandedly reenact Thermopylae"
Baldur's Gate. Minsc, especially in the second game, as his already-tenuous grip on sanity seems to slip further and Jim Cummings really throws himself into the role. This is, after all, a character who believes in solving problems with swords, thinks "shirking" is a painful sharp thing you do to people who would steal nuts from squirrels, and gets most of his inspiration from a hamster.
A miniature giant space hamster no less.
Who is mighty and wise and probably quite stringy.
Minsc's insanity gives players what is actually one of the most hilarious ways to get into Spellhold Asylum. Can be found in its entirety here. His fight dialogue:
Minsc: Butt kicking for goodness!
Minsc: I grow tired of shouting battle cries when fighting this mage. Boo will finish his eyeballs once and for all, so he does not rise again! Evil, meet my sword! SWORD, MEET EVIL!!
Minsc: What? Boo is outraged! See his fury! It's small, so look close. Trust me, it's there.
Minsc: Go for the eyes Boo, GO FOR THE EYES!
Minsc: (as he is promoted to party leader) Magic is fine, but now Minsc is in charge! Swords for everyone!!!
Minsc: (alternate party leader promotion quote) Minsc will lead with blade and boot! Boo will take care of the details. *squeak!*
HK-47: Statement: It's just...you have all these squishy parts, master. And all that water. How the constant sloshing doesn't drive you mad, I have no idea.
HK-47: My master had quite the collection of tortured individuals that seemed unable to confront their basic personality conflicts. Let me cite some specific examples. Mockery: (as Carth's voice) 'Oh, master, I do not trust you! I cannot trust you or anyone ever again!' Mockery: (as Bastila] 'Oh, master, I love you, but I hate all you stand for, but I think we should go press our slimy, mucus-covered lips together in the cargo hold!' Such pheromone-driven human responses never cease to decrease the charge in my capacitors and make me wish I could press a blaster pistol to my behavior core and pull the trigger.
Jade Empire. Black Whirlwind, to whom killing is like drinking wine.
Black Whirlwind: These Lotus Assassins really aren't all that tough; they're just trained well. I've seen men a lot tougher than this run scared from a fight, but not these guys. They're like well-trained dogs, and just as dangerous... though they smell slightly better, and I'm willing to bet they wouldn't taste as good over a plate of rice. Damn it, now I'm getting hungry... and thirsty. Let's get this finished so I can get something to drink.
Effective use of the Vanguard'sCharge ability requires a degree of this, since you're flying headlong into the middle of the enemy's ranks. If that doesn't do it, you can use the Nova ability to biotically explode your barriers in their faces.
In the third game, Shepard has taken to charging at Reaperson foot before destroying them!
In the first game, upon seeing that the Conduit is seconds from closing, Shepard decides that the only option available is to gun the throttle, charge through a ton of Geth including several Colossus and hurl the Mako through a Mass Relay. Considering that Shepard has no way of knowing if either they nor the Mako could even survive the trip, this plan was downright bonkers in retrospect.
Anytime Shepard gets behind the wheel tends to involve a degree of this, such as the above example on Ilos and the Ilium car chase in Lair of the Shadow Broker.
Jack is stark raving mad and awesome enough to tear apart three YMIR mechs with her bare hands (despite the fact that they are still rather difficult boss monsters individually at that point in the game).
Though she is much more serious than the typical example of this trope, and the link between her craziness and her awesomeness is sufficiently well-explored that she probably serves as a Deconstruction of this trope.
Tales of Hearts took this one step further and gave Hisui two arm-mounted crossbows.
Anise Tatlin from Tales of the Abyss has the crazy awesome fighting style of riding on the back a giant, animated teddy bear, which then proceeds to plow enemies into the ground like it's nothing. HOLY SHIT.
King Richard of Windor - Badass with a sword, King of a major nation, extremely pretty...also possessed by a space demon Energy Being and totally hell-bent on essentially destroying the planet. Watch any anime cutscene from Tales of Graces and tell us he's no badass...then watch his infamous TOMODACHIII HUAAAARGH breakdown and tell us he's not nucking futs.
Patricia Tannis from Borderlands. She leaves a series of recordings you can listen to, following her quick descent into various forms of madness. For example, after killing an intruder, she then comes up with an entire backstory and name for him out of starvation for human contact. All this after a rocky relationship with her personal audio recorder? Also, she was the person to actually discover the location of the Vault?
Several playable characters qualify as well, the most obvious being the Borderlands 2 DLC character Krieg, the Psycho.
If he's anything like Naked Snake AKA Big Boss, who practically finds zen enlightenment from hiding in a cardboard box, then yes.
Otacon's argument was that Snake was insane for going up against a tank with grenades, alone, and winning, and not finding that remotely unusual. However, amongst other things, Snake has punched a man dressed entirely in metal plates, identified a female soldier by stalking her until she needed to use the bathroom, grabbed a statue's penis, deliberately enticed a wolf to pee on him to disguise his scent, blown up a rat with industrial explosives, disguised himself as a woman, disguised himself as a corpse, shot a bunch of hamsters with a machine gun, shook a woman to death using a psychic puppet, and hatched an owl from an egg to use its hoots to convince a guard that it was nighttime. Big Boss has murdered people with a fork, recharged his batteries by eating glowing mushrooms, disguised himself as a bishounen, an androgynous Japanese diety, a zombie, a monkey and a crocodile, and defeated enemies by tying them to helium balloons.
Eggman's plans include: Trap Sonic in a space ship, drain the chaos emeralds from his BODY, power up a large gun, blow up the planet, then turn around and build an amusement park.
Doctor Wily from the Mega Man series. He built a robot made of wood.
Wily in the Battle Network series, too. He constructed the server for SoulNet inside an active volcano...and it works. He also has the balls to walk into said volcano while aforementioned server is exploding (NOT from the heat of the volcano, mind you) and give his son, Dr. RegalLaser-Guided Amnesia that makes him forget all about what he's done for the past two games.
Saints Row. Any of the major Saints will have an element of this, but Johnny Gatt and the Boss are particularly vibrant examples.
Male Boss 1: (while on top of a huge steel ball dropping 30 stories just to catch up to Loren) I'M COMIN' FOR YA, FRENCHIE!
Faust from Guilty Gear. He's nucking futs, even after his Heel-Face Turn. Turning into a baseball player, swimming through air, attacking you with a giant scalpel, and implanting a nuke on you, all while trying to save the world. Gotta love him.
Also Slayer, whose Insta Kill involves punching you to a different galaxy using only the power of haiku.
Well, there's a reason why he's in the Tropes Pantheon as the God of Trolling.
Also from Blazblue, Bang Shishigami, who is so Crazy Awesome that listing everything he's done would probably double the length of this page. Suffice to say, his super mode involves him jumping into the air, yelling the most manly battle cry ever, and then teleporting and dashing around the opponent with THIS plays.
"Quicker then the wind and as still as the forest! Hotter than flames AND MORE MAGNIFICENT THAN A MOUNTAIN!"
Also from SSFIV, Hakan. A blue-haired, red-skinned Turklish oil wrestler who lugs around a gigantic barrel of said oil with him everywhere he goes (think Gaara's giant gourd of sand), which he then proceeds to dump on himself at the beginning of every match. His moveset revolves around using his oily body to slide around the arena, and one of his Ultras has him almost literally launching you out of his ass. His motives for joining the tournament are no less crazy. While most of the others are there to defeat a rival, destroy the world or some other dastardly plot, Hakan simply wants to travel the world to find the best olive oil. He's stated to be a multi-billion dollar Olive Oil Tycoon, so he could have done it without travelling the world beating people up. He also has a hot wife with 9 daughters he loves very much.
Father Grigori from Half-Life 2; a Badass Preacher armed with a shotgun, holed up in the zombie-infested city of Ravenholm, where he's not only survived against the monstrous hordes, but also built several traps to kill said hordes easier on his own. Including at least three cars suspended in the air that are bound by nothing more than a few ropes, that act as falling anvils of death. The "crazy" part comes from the fact that he views the zombies as his congregation, considers shooting them in the head their salvation (he's not wrong there, though), and seems to genuinely care about them.
It's possible - and never entirely confirmed or disputed - that one day, Heck just happened to think it would be cool to become a super-secret operative and so became one on strength of nothing but his sheer undiluted batshit.
Also, he invented his own style of martial arts based on unpredictable movements and his own insanity.
In Just Cause, Rico Rodriguez has this as part of his job description. Part of the tutorial for the second game involves a carsurfing gunfight and two fights against helicopters with only his pistols and Grappling Hook Gauntlet. The hook itself allows for absolutely insane things (such as strapping a bad guy to a passing jumbo jet). The craziness keeps ramping up throughout the story, including a fights against an APC and a Kill Sat-
Durandal of Marathon has some elements of this: he loves composing songs and poems, waxing philosophical, and is very, very snarky. Some of his antics include "The Humbling of Battle Group Seven", in which he took on an entire Pfhor fleet with a single upgraded medium-sized ship and almost won, carving an epitaph (in Latin) into a moon visible from space using a Wave Motion Gun, and scaring the crap out of humanity by buzzing Earth in a Precursor warship for the lulz.
Cave Johnson of Portal 2, CEO of Aperture Science, and a grade-A certified Mad Scientist whose inventions are both brilliant and hilariously dangerous. His finest moment, though, is his proposal on what to do when life hands you lemons...note "When life gives you lemons, don't make lemonade - make life take the lemons back! Get mad! I don't want your damn lemons! What am I supposed to do with these? Demand to see life's manager! Make life rue the day it thought it could give Cave Johnson lemons! Do you know who I am? I'm the man who's gonna burn your house down! WITH THE LEMONS! I'm gonna get my engineers to invent a combustible lemon that BURNS YOUR HOUSE DOWN!" And it's actually not out of the question that he did.
Champions Online has probably one of the most awesome villains ever... in the form of the lunatic Foxbat. Using a ping pong ball gun that launches custard pies, massive amounts of pre-chewed bubblegum, high exlosives, and the homing device for an orbitally launched ten ton weight (that says "Ten Tons" on it), as well as robot fan boys, he proceeds to: 1 ) Use voodoo dolls to mind control an entire clan of vampires as part of a bid to marry a Superhero / Pop Star, 2 ) Manage to get a time machine that (in an alternate timeline) required more power than the city's power grid to work to somehow work multiple times, grabbing cowboys, samurai, vikings, cavemen, and Roman legionaires to help fight fallen angels, and 3 ) Takes over a local TV Station so he can broadcast the Foxbat show, in "thrilling Fox-O-Vision". Oh, and lines he spouts when fighting you include asking you if you want to be his sidekick. Only Grond has become more of a meme in the CO universe than Foxbat.
Lollipop Chainsaw is fixing to be this. In short, Buffy carrying around the severed head of her boyfriend as she uses a chainsaw to slice rock zombies in half from the groin.
Then there's Baofu in Eternal Punishment, who is a creepy guy with a perpetual smug smirk in sunglasses and a gold-colored suit. He never stops snarking at and insulting everyone around him, his choice of weapon is coins flung fast enough to hurt, and he can try to blackmail demons - and succeed! (Though some just think the mere attempt is hilarious.) Oh, and he's also on a personal crusade against the Taiwanese mafia.
While most people in Monkey Island deserves a mention, Guybrush Threepwood, while appearing normal on the outside is crazy once you think about it (sort of related to how the games themselves work), but he's killed zombie pirates by spraying him with root beer, he once locked a man in a coffin (which he sold, used) to steal a key, he took instructions to complete a maze by listening to his dead parents singing it to him in a dream, he purposely drank poison to kill himself, then coming back to life to claim a life-insurance all while stealing just about anything he could see.
Hatoful Boyfriend has Oko San, a super-fast track star pigeon who's completely obsessed with finding the perfect pudding that will awaken the pudding god and banish sadness forever. No really; he accomplishes exactly that in one of his endings where he becomes the pudding god himself and turns the entire world into gooey happy pudding.
In fact, Anghel Higure's route is the only one in which Dr. Shuu is actually defeated; all the other routes have you escaping his attentions (knowingly or no) or getting murdered.
Both Anghel and Oko San have moments of saving the day in the "Bad Boys Love" route, specifically because of the things that make them crazy: Anghel's hallucinations cause him to be more aware of actual threats and able to warn (in warped metaphors) and rally the other birds in response to said threats; Oko San's speed lets him pull a Big Damn Heroes moment, and his ignorance of social complexities enables him to reassure Sakuya when the latter is a broken haughty.
Holiday Star has Fallen Chronicles: Absolute Zero, where Anghel's unique quirk is weaponized - and countered by enveloping people in a fantasy that they are Magical Girls and using their magic powers to create a shield.
Let's not forget the biggest example of Crazy Awesome here...Moa, the game's creator. Making a Visual Novel/Dating Sim where the entire cast (except for your character) is birds? Crazy. Making such a game one of the greatest things you'll ever play? That's where the "awesome" half of the trope gets tacked on.
Xenobladedeconstructs this with the character of Dunban - while he is an awesomelyBad Ass character, his recklessness severely damages his right arm and almost gets him killed. Ultimately, the much more restrained Shulk gets his Monado, and he ultimately takes a level in badass when he gets a level in common sense.
Realm of the Mad God has Oryx, the titular mad god and a Drunken Master, at least according to fanon. His exploits include taking pity on orphaned drakes by turning them into trees, creating the recursive Mook MakerCube God, and reanimating his own puke (okay, it's bile, but you get the idea) to battle you if you trespass in his wine cellar.
The Panic Room campaign in PAYDAY: The Heist is based on being crazy awesome. The crew plan to rob a gang of drug dealers of their money, but the money is inside a fortified panic room. Does the crew brute force the door open? Nope. Do they interrogate the gang for the door codes? No. Blast the room open? Hell no! The crew steals the entire room by detaching the panic room with some saws, plant C4 on a few floors to blow a hole to the roof, and have their helicopter pilot airlift the panic room out with an electronic magnet.
While many bosses in the Metal Gear franchise would qualify, the patron saint of this trope is probably Fatman, a bomb-slinging man in an oversized flak jacket who rides around on rollerskates. If that doesn't qualify for Crazy Awesome, nothing does.
The Avatar in Fire Emblem Awakening. Informed that the enemy's fleet has just as many ships as them and the enemy ships are packed with soldiers while most of the good guys' ships are only half full, s/he decides that since they can fit all of their soldiers on only half of their ships, they should have half of their ships ram the enemy fleet, then set their own ships on fire and evacuate everyone to the other ships. Caught between multiple armies, s/he limits the enemy's avenues of attack by luring them to an active volcano. Needless to say, the Avatar certainly believes that fortune favors the bold.
Disgaea sort of specializes in this trope, as it takes place in a combined World of Ham / World of Badass. There are probably too many individual examples to list, but one of the first notable ones is Laharl; his ultimate attack involves jumping into outer space, landing on a passing giant meteor, and riding it down upon his enemies' heads. While laughing maniacally.
Cysero from Dragon Fable. He decided to stuff some people into a Tardis-esque time machine just to see if they would fit. They didn't even have to be in the time machine in the first place.
And that's ignoring how blase everyone is about him having made a time machine. As a later storyline shows, Cysero doing stuff like breaking spacetime is so commonplace it's not really worth getting excited about anymore.