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It's on the tip of my tongue... It ran for many chapters (I think, to a reasonable conclusion), as well as a sequel, and a side story in "the other pants leg of time" (yes, they acknowledged borrowing from Discworld). The basic premise of it, as I remember, is that yet another bizarre martial artist shows up, but in a twist, he's after Ryoga. He also wields an umbrella, but his is a fancy black one, which he wears with a dapper suit (at one point, he points out his annoyance with how his theme results in him having to replace a lot of suits due to fights). He has a younger sister, who has a bit of a crush on Ryoga. When he explains why he's opposed to Ryoga, I seem to recall it more or less came down to that Ryoga showed up at the school (entitled something like "The School Of Unorthodox Combat Weaponry") and learned the umbrella techniques effortlessly (umbrellas were only one branch of it, although I remember them referencing The Penguin and I think Shizumaru Hisame as people who trained, or had trained, at the school. His little sister did some other weapon).

After much fighting back and forth, with the new antagonist doing his best to maim Ryoga while Ryoga treats it as friendly combat just like it always is in the series. Bits that I remember include an all-night Jackie Chan film festival with most of the characters attending at one time or another between fights (Ukyo dressed up in a trenchcoat for it, I think to watch Ranma and Akane on a date?) and a climactic battle on a bridge between the new guy and Ryoga.

That battle was a big set-piece in the fic. They meet on the bridge and respectively destroy opposite ends of the bridge using the Exploding Point Technique (the rival had picked up the Exploding Point technique by watching it being done, and had thus missed out on the toughening aspect. He was very disappointed to find out it didn't work on flesh after he tried to poke Ryoga with it). During the battle, there's a part where the rival throws his umbrella much like Ryoga does, and it's noted that his technique isn't as good, which means the umbrella kind of loops around unpredictably. And near the end, they wind up doing multiple chained suplexes to each other before the bridge gives way and they're washed away.

For a while, both of them are gone with the younger sister wearing Ryoga's bandanna in memory of him. There are interludes involving amnesiac umbrella-wielders where it's left ambiguous as to which one of them it is, including something where they run into M. Bison and accidentally get some of his Psycho Power. At some point, they both come back. The rival has been working as a criminal enforcer (I think as some sort of hitman) and is now able to concentrate that Psycho Power into the leather gloves on his fists (there was a scene where he stood on a rooftop and continuously "flexed" the power into his fists to get stronger) and has also figured out a way to use the Breaking Point Technique on living things (he has a needle point on his umbrella, and triggers the Breaking Point on the bone).

The spin-off fic (or maybe it was the sequel) had the same characters, but were traveling through dimensions due to a locket of some sort.

I read this probably in the early 2000s? It was on an author's website, but so many of those have gone down over the years. I don't remember what other stories might have been on the site.

Another thing I just now remembered, the author also did an MST of the infamous fanfic "Ukyou Can Cook" using the original characters from this story.

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After doing some Google searches targeting thekeep.org, which seems to be one of the larger bastions of Ranma 1/2 fanfic, I tried site:thekeep.org gaijin umbrella (hoping to find it via the side reference to The Penguin being the gaijin teacher at the school where they studied combat use of the umbrella) and got a chapter of "The Pursuit of Happiness", which sounded familiar. I clicked into that, and then up the chain, and the name of Ryo sounded familiar. It's a sequel to "The More Things Change", which has a side story of "Converging Series". "The More Things Change", by RPM, was what I was looking for, probably first read off of the M Productions website.

You know the old saying. THE MORE THINGS CHANGE... the more they stay the same. Ranma chooses Akane! Akane chooses Ranma! Within the span of a day, things seem to be changing drastically in Nerima, with that one important issue cleared up. Life seemed to be settling into an almost normal state. And then Ryouga got engaged to Shampoo... and then there's that chemical accident with Kodachi... did we mention he's living with Ukyou? And now there's someone from his past with a grudge showing up... does all this sound familiar?

The antagonist was Ryo Muhoshin, who looked like Gosunguki in a suit, and indeed, the catalyst for the rivalry was Ryoga showing up out of nowhere to interrupt a curb stomp of another student, and then proceeding to outpace Ryo, much to the joy of the teachers of The Unorthodox Weaponry School of Martial Arts who were worried about Ryo's sadistic tendencies. Indeed, there's a Jackie Chan film school. I'm pretty sure that, with a little more digging, I could find all of the other references too, but that's enough to satisfy me that I found the right one. Oh, and The More Things Read was where I remembered the MST from.

FWIW, the other trouser leg:

This, the 'right trouser leg of time', is the one that theologists of the pantleg school of chronal theory generally refer to as the 'main' timeline, or leg. The leg that's at the center of things anyways.

For example, if the reader wishes to follow the right leg, they'd stop right here and read part twelve.

The other leg, however, the 'left leg' of the trousers, is generally used to describe 'alternate realities', where things aren't as they normally are.

Of course, the left pant leg is the one that the scientists aren't in, so by logic the left trouser exists only in theory. However, this doesn't stop the scientists from wondering exactly how things might be different in the other leg.

Yet another branch of time theory insists that if moments of destiny were branched off like trousers, those trousers would have a bloody lot of legs to fill.

Anyways, this is how one of those non-right legs went...

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