Crazy Awesome/Tabletop Games

Mortasheen as a setting has plenty of this, but one of the most notable examples is Harlequeen, which is noted to be blitheringly insane even by Joker standards, but their plans turn out as if they had been calculated by a tactical genius.
Pretty much every popular Ork, and half the popular characters period, in Warhammer 40,000. Crazy and awesome are both plentiful in this setting, but Orks really excel at combining the two. They're so crazy that their technology is fueled by Insane Troll Logic and STILL manages to work......somehow.
- Then there are characters that are Crazy Awesome by Ork standards, like Mad Dok Grotsnik. There aren't that many beyond that though, as most characters in Warhammer 40000 tend to go from being awesome to being Complete Monsters the crazier they get, like Fabius Bile and the entirety of the Dark Eldar.
- Wazdakka Gutsmek is an Ork who decided his bikes guns weren't big enough. So he mounted fully automatic tank cannons on it. And thats tame by the standards of most Ork Characters...
- Kharn the Betrayer, according to Memetic Mutation.
- And the Skaven over at Warhammer Fantasy Battle
- Also Eldrad Ulthran at least according to http://1d4chan.org/wiki/Eldrad.
- Ork freebooter Kaptin Bludflagg.
- If you aren't Crazy Awesome in the Warhammer or Warhammer 40000 universe, you won't live past 2 seconds.
Mr. Welch is the embodiment of Crazy Awesome.

182. No figuring out the plot and killing the actual villain five minutes into the adventure.
337. Even if the rules allow it, I cannot control 20,000 pigeons and use them as flying piranha.
598. Any adventure that ends up with my character being worshipped as an orc god was just a dream. Retroactively if need be.
680. My axe doesn't go off accidentally when I'm cleaning it.
806. My character cannot have a noticeable impact, positive or negative, on a town's population.
1273. Any character that makes a seasoned Rifts player flinch is vetoed, and shall never be spoken of again.
1317. My character will refrain from appearing with Hitler in any history books. Especially if I?m chasing him with a wheat thresher.
1411. Despite what the rules say, bobsledding through the Vatican is much harder than it looks.
1939. Even if the rules allow it, can't parry an artillery barrage with my fists.
1951. Can't use the international date line to get around once per day restrictions.

Most successful games of Genius: The Transgression:
- To give two examples, the first playtest game ended up with Lemurians in a flying giant metal squid attacking a Nazi island by draining a giant emerald shaped like Hitler's head. The second playtest game ended with the PCs fighting Nazis on top of a blasphemous pyramid in Jakarta, with one character directing temporally displaced Persians from atop a jury-rigged flying machine and the other going toe-to-toe against the Big Bad to stop him from sacrificing the PC's sister to release a Timeline eating True Fey.
- Another game started with a character stepping off Hauptmann Kreuzfeur's Eargersplittenloudenboomen Fliegeden Untertasse. Words fail.
Pretty much every incarnation of The Loonie player archetype attempts to be this, although the balance between crazy and awesome varies.
Exalted. It has two martial arts dealing with flamethrowers and another that uses a chainsaw version of Captain America's shield. The main characters are assumed to go Serial Escalation on a daily basis. The default starting character types, the Solars, have to deal with fate ninjas who don't like them, elemental-powered samurai monks who really don't like them, and extradimensional living cities that absolutely hate them. Oh, and the mechanical spiders that control fate have a soft spot for feats of epic awesomeness, making the really insane stuff more likely to succeed. Given that it has been described as Dungeons & Dragons meets Tengen Toppa Gurren Lagann, this was frankly inevitable.
- The Ink Monkeys blog has produced some new enhancements. References to a First Age Solar setting up a special location for using tyrannosaurs as skis are just the start.
In the Pathfinder Campaign Setting, there is the deadly Test of the Starstone, which turns any mortal who passes it into a god. The adventurer Cayden Cailean went on a roaring drunken bender one night and took it on a dare. He woke up the next morning as the god of bravery, freedom, and alcohol. He still doesn't remember how he did it.
There's also the infamous Old Man Henderson, the only man who ever won at Call of Cthulhu (tabletop game). Specifically, he did this by BLOWING UP GOD-DAMN HASTUR WITH AN ICE RINK FILLED WITH DYNAMITE AND C-4.
- The crazy part comes in when you realize that this is a heavily Mini Maxed Schizophrenic Scotsman who's convinced he fought in Vietnam when he really didn't, and is a Crazy Survivalist to boot. He also joined the investigators solely because he thought Hastur had stolen his lawn gnomes.