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Kingdom Hearts was definitely a big shock. Though it's less of a full on crossover and more of a Disney game with a splash of Final Fantasy (till now...)

When I read Snake was going to be in Smash in IGN (they showed the trailer first behind close doors to press at E3) I legitimately thought it was some kind of prank.

Nobunaga's Ambition and Pokemon was not a crossover I was expecting, mainly because what the fuck is Nobunaga's ambition. Surprisingly good game though.

Sonic and Mario at the olympics was surprising. Just cause we never thought we would see it... and when we did it was in a Sports minigame collection. Someone made a magic monkey paw wish.

Spoiler!
Donkey Kong.

in Punch Out!!!

Going along in title defense mode... Got two losses but feel like I have a grip on the patterns. Then this fucker comes along. 

But the biggest surprise gaming crossover has to be Mario and Rabbids. Because that was three surprises in one.

First, when it leaked you were surprised that this game was being developed in the first place. What does Mario have to gain from fucking with Rabbids who have been irrelevant since minions came along?

Second, it was surprising when you actually saw what the game was. Wait... this isn't a mini-game collection? It's a turn based tactical shooter? Wtf?

Third, it was surprising that the game was actually really fucking good. Nobody saw that coming.