Okay, here's a convoluted attempt to go from "Lemmings" to Hitler:
Lemmings (video game)
The Good, the Bad and the Ugly
PCF theory
Power set
Multigraph
Ordered pair
Coordinate system
Galilean transformation
Ball
Kitten
Average
Domesday Book
Honey
Radioactive decay
Avalanche
Pyroclastic flow
Sumatra
Marco Polo
Coal
Lewis and Clark Expedition
Beaver
Israel
Bible
Kabbalah
Tiferet
Abracadabra
J. K. Rowling
Monty Python
Tim Curry
Four Dogs Playing Poker
SAV
Erwan Vallerie
Nono
List of Planetes characters
Cattle mutilation
Space Invaders
List of Robot Chicken episodes
Adolf Hitler
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I started with "Lemmings" and did the same thing as last time, but right around when I got to "Beaver", I thought I should start from the end and try to make the links into Hitler as unrelated to Germany or Nazi etc. as possible. So I did that, making use of the "What links here" feature of Wikipedia. That eventually leads up to "Bible", and surprisingly it was only 2 clicks to go from "Beaver" to "Bible", so boom!
I do think making Hitler the endpoint makes the game a little too easy. A comparatively more esoteric topic like "Lemmings" might make for a more interesting endpoint for this sort of game.