Britney - It's like no one see's the light her fans see. (Or those wack ass closet stans pretend they don't)
Miley Cyrus - Can sing, write music, perform, act (all very well) and more yet people write her off because she's a teen star.
Christina - So, so, so, musically and commercially under rated. Like her music is amazing. I know it's subjective but I think people would really like her music if they looked past the floppage and her "attitude".
Missy Elliot, she was a pioneer of creative music videos (going back to the 1990's). Beastie Boys in terms of breaking the racial barrier in rap/hip hop music (before Eminem ) Grace Jones with her fashion.
I've realized through this whole Push and Shove era that No Doubt is too underrated for their status. They have a decade-crossing career, a string of popular hits, and a unique and dare I say 'future classic' discography? They don't get the recognition other long time acts get, perhaps due to the hiatus? But Gwen had a successful solo stint during the hiatus, so you would think more people would be here for them still. It's just weird to me, they should just be massively successful for their status.
Others: Kelly Clarkson, Ne-Yo, Jason Mraz, maybe P!nk, Missy Elliott, and Kylie Minogue in the US