Why is Ashley so popular?

Ashley's popularity comes from 3 factors.
She has a cute and simple design with a slight gothic/halloween vibe to it, a somewhat relatable personality that makes her stand out from the rest of the more upbeat Warioware characters (For better or for worst, depending on how you see it) and has a pretty catchy song to boot.

There's some other variables in there too (Such as her song being in Smash Bros.) But those are the 3 main big factors really.

At least, based on my experiences around social media. (Which is 100% totally and utterly scientifically accurate, no questions asked!)
 
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I think there's some snowball effect involved: Nintendo is aware of Ashley's popularity, which makes them decide to give her more attention, and that in turn makes Ashley gain even more popularity.
 
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