The Justice League Unlimited version of The Question is a conspiracy nut who is an excellent detective perhaps because of his paranoia. He's also depicted as being highly eccentric; in one instance, he interrogated a man using a girly pop song, and then was later shown humming that same song while casually smashing through a glass door. By his own admission, he rummages through everyone's trash and believes the Girl Scouts of America are responsible for crop circles. When Batman recommends him for a major investigation, everyone at the League's fancy conference table groans. Upon being tortured:
Interrogator: Tell me what you know! The Question: The plastic caps on the ends of shoelaces are called aglets. Their true purpose is sinister!
His origin story in the comics shows that he isn't (or wasn't, anyway) really crazy. He puts his costume together as a spur of the moment disguise, and when the first opponents he encounters afterward freak out because anyone that would wear that is clearly nuts, he decides to play it up for effect. Cultivating a reputation for being so crazy the Joker steers clear of you is actually pretty brilliant.
The Justice League Unlimited version of Toyman is about the only guy in that world that can beat the crap out of other supervillains with a yo-yo.
I shall now quote the opening theme. "You dig giant robots, I dig giant robots, We dig giant robots, CHICKS dig giant robots."
Only Ms. Frizzle from The Magic School Bus could get away with putting children in mortal danger on the inside of a magical school bus. And this is why she is better than you.
Freakazoid! is pretty much the Anthropomorphic Personification of Crazy Awesome. He's got a Freakmobile, the ability to travel through Cyberspace, and can turn into lightning, but prefers to get around by throwing up his arms and making whooshing noises. He's got super strength, but will more often than not defeat his opponents by confusing them into submission or whining at them until they run away. As the theme song puts it:
He drives the villains crazy, 'cause he's a lunatic!
Freakazoid promptly cemented himself as Crazy Awesome forever by the way he denies looking at Jeepers' magic watch, which also showed kids how to handle creeps in real life: scream at them for two minutes until they crawl away.
"NOOOOOOOO!!! GET OUTTA HERE WITH THAT WATCH! LAY OFF THE POOR BEAVERS, WILL YA?!? SHEEEESH! YOU'RE A CREEP! GO AWAY! WE WERE ALL HAVING A GOOD TIME UNTIL YOU SHOWED UP, JEEPERS! UUUUUUUUGH! GO HAVE SOME COFFEE, WITH CREAM, OR SOMETHING! BECAUSE I'LL TELL YOU SOMETHING: THIS IS A HAPPY PLACE!!"
In the one-shot Jonny Quest spoof, Toby Danger, the Race Bannon expy Dash O'Pepper certainly qualifies, down to his perfect impression of Mike Road. "JUST LET ME THROW A BARREL AT IT!"
Clopin from The Hunchback of Notre Dame. He has an oddly adversarial relationship with his hand puppet, and presides over a bizarro Kangaroo Court where he captures, tries, and nearly executes the movie's heroes—all in the span of three minutes. And this guy is also the heroic leader of the rebellion against Frollo.
Stork of Storm Hawks. In an episode when the Condor is laid low and being invaded, Stork holes up in the cockpit—which the villains manage to break into anyway. Cue Stork activating innumerable traps, as he mutters about the rest of the Storm Hawks laughing at him for putting defenses in an area of the ship boarding parties won't reach. All of them, incidentally, work without a hitch. Crazy Awesome.
Although it doesn't always result in success, eponymous Invader Zim invokes this trope on numerous occasions, such as flattening a city with a water balloon, altering the past with rubber piggies, and setting a giant hamster loose in the city to create havoc.
GIR also fits this trope—heck, pretty much the entire cast does. Not so much Dib. Definitely Gaz though.
Soundwave. Reasons? 1) He uses a guitar (and later, a keytar) as a weapon. 2) His minions Laserbeak and Ratbat transform into said guitar and keytar, respectively. 3)He's a "freedom fighter" for machinekind on earth. 4) It's friggin' SOUNDWAVE we're talking about!
The original series had some moments as well. For example: A mental hospital planet, in an all-else-has-failed attempt to cure Galvatron's insanity, has him interfaced with their planet for lobotomization. He immediately drives the planet insane.
One mustn't forget Wheeljack, a mad scientist who creates weapons of mass destruction and transforming robot dinosaurs, and he's a good guy. Said robotic dinosaurs are Crazy Awesome themselves, being fire-breathing robot dinosaurs that transform into robots, have no respect for the main hero, don't care what they smash, and they're also good guys.
The Joker, because he can't be mentioned enough times. "I should've picked the fat guy."
Escaping a madhouse by riding a Christmas tree that was also a rocket right out through the roof, all while singing "Jingle bells, Batman smells"? Yup. And keep in mind this was his first scene in his first episode.
King Bumi — there is no end to his crazy awesome shenanigans.
Aang: Bumi, you're a mad genius!
Aang later named his oldest son after him. In his brief introductory appearance in the first season of Legend Of Korra, he demonstrated he was worthy of his namesake with his one line of dialogue.
Bumi': WWWWWWWWWWWWWOOOOOOOOOOOOOOOOOOOHHHHHHHHHHOOOOOOOOOOOOO! *claps and grins crazily*
From Season 2, we are introduced to Varrick, a fun-loving corporate executive. A mad inventor who invented film for fun, whose girlfriend (?) is his smoking hot leading lady, and who, when he gets in a pinch, hides in a Platypus-Bear to remain undetected! Oh, his yacht? It's also a giant speedboat and carries a biplane ("What sort of ship wouldn't have a plane?") but no runway. Not only that, he owns one of the very first Battleships ("I wanted one so I got it!"). When he's later arrested for attempting to kidnap President Raiko, he reveals he has already built himself a custom cell in the prison which his company made since he always thought he'd end up there someday, and finally when his cell is busted open during Unalaq's attack on Republic City, he immediately puts on goggles and Zhu Li, his Hyper Competent Sidekick, jumps onto his back, attaches herself to him and they both fall out of the cell, then glide away on a glider he had just in case!
Varrick: Zhu Li...do the thing!
Zhu Li: *attaches a box to her back, runs over and jumps on Varrick's back and both jump out of the cell and glide away*
Red Hood. Considering he's an alternate (good) version of the Joker, it stands to reason that he'd also be crazy awesome, and he definitely is. He laughs maniacally while being tortured, saying, "Oooh, tickles!"
He wears the completely-lacking-any-kind-of-hood-but-quite-red-indeed Red Hood costume originally worn by Joker before he was Joker. And is still much too awesome to have been confined to one episode.
Jade from Jackie Chan Adventures is the epitome of the trope. I mean, she replicated herself several thousand times to beat Po Kong the Mountain Demon. She uses Stealth Hi/Bye in every episode, along with Off Screen Teleportation. She manages to stall the Demon Sorcerers from eating/destroying her until a portal enables her to escape the Netherworld (and still has time to blow a mock kiss at Hsi Wu). She tears a page out of the Book of Ages, for crying out loud!!!
Ben Tennyson from Ben 10 and itssequels, on his better days. He's a kid/teenager with a watch that makes him a Henshin Hero, and uses it exactly how you would expect.
His Crazy Awesome alien form Rath takes the cake. Basically, he's a tiger standing on two legs who looks like he took trash talk lessons from Randy Savage or Hulk Hogan, and fights like them. He cemented his Crazy Awesome status by jumping down into the stomach of an intergalactic overlord to save the prince of a planet he had to tend for and threatened that he'd knit a sweater out of his organs if it happened again because "EATING BABIES IS NOT! COOL!" Not to mention that he is super strong, very angry and all around BADASS.
Hunter Gathers from The Venture Bros.. The man faked a sex change to avoid capture, for one. He's also Brock's mentor, and a truly badass one at that. "...Are you still ready for anything?" "Ye-" "Wrong! *slices Brock* Lesson number one, trust nobody. The second God crapped out the third caveman, a conspiracy was hatched against one of them. Get up, damn you!"
For the record the sex change wasn't fake. He actually had a sex change operation. Twice.
Then there's his boss... General Treister.
I want notes, lists and answers by the time I finish this here Juicy-a-Box! WARNING: I am Thirst-ay! And it is Fruit Punch! And it is Delicious!
General Treister outstrips Hunter Gathers by miles: the season 4 finale has Treister pretending to think he was a 'hulk' to root out traitors in his organization. He then revels that he engineered the circumstances for Hunter Gather's defection to see if he had the balls to replace Treister. And he tops it off by reveling he has cancer, and launching himself into space in a rocket wearing nothing but an American flag and a sticky note that says 'Fix It!', addressed to alien races that may be able to cure him.
Cheese Sandwich from "Pinkie Pride" pretty much outdoes Pinkie Pie as party planning pony. That Party Cannon Pinkie has? He has a Party Tank. He's also got "Weird Al" Yankovic as a voice actor. His episode escalated into an all-out duel for the title of the ultimate party pony, before he revealed that he was anything but the Life of the Party until Pinkie inspired him.
Pinkie Pie's older sister Maud Pie (from the eponymous episode) continues the Pinkie trend with her obsession over rocks, her emotionless deadpan tone, and her ability to throw rocks over the horizon that are unlike bombs going off and pummeling boulders into rubble with her bare hooves. She is loved by a lot of the fanbase.
The Space Pirate Hondo Ohnaka from Star Wars: The Clone Wars has earned this as of late. Not only does he have the balls to snark off to not just Dooku, not just Grievous, but also Darth fucking Maul, he just so happens to fight off droids not with a blaster...but with a sword. This guy breathesCrazy Awesome.
Gravity Falls: Mabel Pines. Ditzy and enthusiastic about everything, but also quite capable of dealing with the supernatural weirdness that pervades the town of Gravity Falls.
Quentin Trembly, the eighth-and-a-half President of the United States. The guy declared war on pancakes, tried to ban pants, and appointed babies to the Supreme Court. He also cryogenically froze himself in peanut brittle... and it worked! He eventually leaves town by leaping onto a horse and riding it backwards.
Old Man McGucket. He's not just the self-declared local kook, he's also a Mad Scientist who builds things like a giant mechanical replica of a local lake monster.
Bill Cipher. He's insane, and our point is that it makes him awesome.
The Simpsons: Groundskeeper Willie, a drunk, insane Scottish janitor who fistfights with animals and apparently thinks movies are real.