A little while back, I was thinking about a Fate/Stay Night scenario with more modern servants and had the most ridiculous yet strangely appropriate idea.
L. Ron Hubbard as Caster.
It works better than you'd think - Hubbard claimed that he was trained by a Blackfoot shaman and went on a spiritual tour of Asia as a child, and Aleister Crowley records him as performing magic rituals with some of his other acquaintances. Scientology could be a deliberate attempt to set himself up as a Heroic Spirit, with the "MONEY" aspect as a plausible cover.
Also, Lee Harvey Oswald as Assassin, with the Noble Phantasm "Magic Bullet."
(Rider is glutted for choice - Manfred von Richthofen aka the Red Baron is the obvious one, but I would pick Erich Hartmann for being the top fighter ace ever as well as being totally balls-out, though I also have a fondness for America's top fighter ace, if only to have a guy named "Dick Bong" running around - as is Archer - Simo Hayha, probably, though really you can go to Badass of the Week and take your pick. Saber is pretty much limited to Jack Churchill, Berserkers would almost all be in incredibly bad taste, and I don't really think there is a modern Lancer.)
L. Ron Hubbard as Caster.
It works better than you'd think - Hubbard claimed that he was trained by a Blackfoot shaman and went on a spiritual tour of Asia as a child, and Aleister Crowley records him as performing magic rituals with some of his other acquaintances. Scientology could be a deliberate attempt to set himself up as a Heroic Spirit, with the "MONEY" aspect as a plausible cover.
Also, Lee Harvey Oswald as Assassin, with the Noble Phantasm "Magic Bullet."
(Rider is glutted for choice - Manfred von Richthofen aka the Red Baron is the obvious one, but I would pick Erich Hartmann for being the top fighter ace ever as well as being totally balls-out, though I also have a fondness for America's top fighter ace, if only to have a guy named "Dick Bong" running around - as is Archer - Simo Hayha, probably, though really you can go to Badass of the Week and take your pick. Saber is pretty much limited to Jack Churchill, Berserkers would almost all be in incredibly bad taste, and I don't really think there is a modern Lancer.)