Twenty-one things one needs to know about one Jiraiya... or not.
1.) Jiraiya spent four months, three weeks, two days, eleven hours and thirty-nine minutes practicing his grand entrance sequence, to the exclusion of anything but sleep and food. It is because of this that he gets so miffed when someone insults it. After all, those who mock him have yet to try hopping around on one foot in a pair of uncomfortable geta.
2.) He is the only man to ever take a direct hit from Tsunade who lives to tell the tale. Where Orochimaru swapped bodies and Tsunade regenerated, Jiraiya was content with nigh-invincibility in life. He thinks he got the best deal of his team.
3.) There is little about sex and sexuality that Jiraiya has not explored in-depth. Yet, while he is no homophobe by any means, performing with another man never resulted in the same kind of extatic pleasure he gained from doing the same with women.
4.) Jiraiya is the only person, living and dead, to know why Orochimaru so desperately seeks immortality. He is the only one who was able to see past the hunger for knowledge and into the depthless, abyssal fear that lurked in the mind of his pale comrade.
5.) He is an orphan, not knowing his origins to his dying day. His burning desire to carve his name into the tablets of eternity stems from lacking a past, and he succeeds beyond his wildest dreams. While he often suspected who and what his parents where, he could never prove it.
6.) His team broke his heart twice over. His nerdy, pale brother betrayed everything they fought for together in the past, broke all bonds of comraderie and cast down all pretense of humanity later in their lives. His brash, quasi-royal sister broke his heart when she gave herself up, when she cast away the spirit he had helped nurture, when she gave up on the memories of their bond. There are times when Jiraiya genuinely wants to kill Tsunade and Orochimaru for those reasons alone.
7.) Despite the fact that his white hair and red face marks never made him good with disguises, Jiraiya is an expert infiltrator. But where others creep silently through the night, clad in grey and green, Jiraiya dresses in the most expensive of garbs, wields his rougish smile like a scythe and gets by virtue of daring and charisma what others fail to achieve by sneakery and silence.
8.) Morino Ibiki will never know it, but it was the white-haired toad summoner who rescued him from the torture-chambers that disfigured him so. Jiraiya, after all, cared for his children, and none of the fools who dared to lay hand upon his family escaped his wrath - even though it took him almost two decades getting the last ones.
9.) On the subject of children, Jiraiya has surprisingly few. Tsunade, in her infinite wisdom, taught him and Orochimaru the best contraceptive jutsu known - or not known - by mankind. He has left a child in every major city of the elemental countries, but, in his own, subtle way, he sees to it that they are properly cared for.
10.) He once wrestled a giant bear into submission, after refusing to back down from the stupid, stupid bet he had made with Orochimaru after a cup or two of sake too many. Still, the multitude of gashes the animal left upon him were well worth the look of surprise on Orochimaru's and Tsunade's face when he rode back on the majestic animal.
11.) Tsunade and Jiraiya are the only people in the world who saw Orochimaru cry. It was when they arrived - after a long, violent campaign against the Grass - at his home for a quick snack that they found his remaining family butchered. While Orochimaru might not have had parents any more, the sight of his brutally murdered sister was enough to drive even the hardiest of sannin to tears.
12.) The three of them, after finding out who was responsible for that started a campaign of bloodshed and terror that the Waterfall Village has yet to recover from. It is one of the few places Jiraiya never, ever visits, because he knows that the demonized version of the sannin the Waterfall knows isn't so far off the truth at all.
13.) He created the needle-guardian hair technique on accident, after an embarassing match against Orochimaru during their shared jounin exam. When Orochimaru managed to miss his shoulder and instead bit into his - long and luscious, so he said afterwards - hair, the shocked Jiraiya simply pushed a lot of chakra into said hair. Orochimaru still hasn't forgiven Jiraiya for the indignity of having to eat through a straw for two months.
14.) There is a special reason why he hates Uchiha Itachi more than any other of the Akatsuki. Just as he did with his children, Jiraiya cared about his students - and even if cute little Miko-chan hadn't become as famous as the boy who grew to be the Fourth, killing one of his former students was, in his eyes, an open declaration of war.
15.) He owns enough clothing to outfit the entire Hidden Leaf thrice over, and only one in ten pieces is nin-wear. He's a smartly dressed man, he will admit that to everyone. And, after all, those who mock him for it should see to it that they look as great as he does when they grow as old as he did.
16.) Jiriaya is a passionate man, living to the fullest in every action - and he has proven this time and time again, from the first time he won an eating contest against three Akimichi to the last time he and Tsunade tried to drown their sorrows and see who'd last longer. Jiraiya is a man who can enjoy the best and worst of food and drink equally, because he knows that every meal might be his last.
17.) He made the crystal scrying ball for the Third. It is his greatest masterwork, the proof of his ability as a Master of Seals. It is this item and the theories involved that made the Third sign the decree that Jiraiya needn't follow the ordinary chain of command or rules of conduct of the Leaf, that he could - and should - do as he pleased. Jiraiya considers it to be the best deal of his life.
18.) Jiraiya hopes Tsunade dies before he does, because if not, he knows that she'll resurrect his carcass, beat him until he'd wish he was dead again and then have him clean up the mess his last will would create. Still, he figures that it'd be nice, if only to see the horrified, disgruntled or panicked faces of all those idiots who'd have to deal with everything from marriage contracts to assassination attempts because of the information he will unleash with his death.
19.) He has never been in a committed relationship - some would say that he is afraid of marriage. Those who say that, though, usually end up being chased by hallucinogen-carrying toads, sinking into suddenly appearing swamps or ending up with otherwise unidentifyable maladies. And yet, despite his vindictiveness, he knows they're all wrong - the only woman he'd ever marry is as broken a wreckage as he is when it comes to commitment, and he doubts that he'd survive a full-on hit a second time.
20.) Jiraiya knows that, for all his passion and zest for life, he has a dark side. He knows that a moment of inattentiveness could lead to depravity on a scale that would send Orochimaru screaming, clawing his eyes out. He knows that one moment of laxity could spawn a lifetime of madness, and because he knows all this he acts upon it, always confining himself to bonds unbreakable. And yet, it is because of this restraint that he grows above and beyond the call of duty, both to himself and others.
21.) Jiraiya has been there, has done that and he has the scars to prove it. He has suffered the biting cold of the uppermost reaches of Glacier Country as well as the parching heat of the desert sun, he knows the unrelenting fury of the oceans as well as the gentle flow of any river. He knows every type of animal, the myriad of insects that exist everywhere. He knows everything and everyone, and Life itself knows him.
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All of this was written before the sad, sad mess that the revelation of our favorite hero's parentage and the real antagonist have wrought. I reject reality and canon and substitute it with my own.