The MC (main character) of the first anime you watched now has to fight the MC of the last anime you watched. Who wins?
If the result is obvious, change it to the entire cast instead of just the MC. For your first anime, try and use the first anime you watched [i]knowing[/i] it was anime. So no DBZ or Pokemon or anything like that.
Mine is [url=http://pluckyoutoo.files.wordpress.com/2009/01/bebop.jpg]Spike[/url] (Cowboy Bebop) vs [url=http://cdn.myanimelist.net/images/characters/4/146293.jpg]Ririchiyo Shirakiin[/url] (Inu x Boku SS)
Spike has experience but Ririchiyo is part youkai, so idk. Ririchiyo has the upper hand but I imagine Spike would be able to defeat her somehow.
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If movies count, the first anime I saw was Dead Leaves, which, I guess, would mean Pandy, maybe Retro, maybe both. Whoever it is would have to fight Natsu or Lucy, from Fairy Tail, or both. Two on two, I have to go Pandy and Retro. Pandy vs. Lucy. Pandy. Retro vs. Natsu. Close call, but I'd have to go with Retro. He's using guns, outside of Natsu's range.