Doesn't have to be a singer/artist, I just put it here because people talk about celebrities here the most.
For me:
India Arie - she's deep, too bad she's going out with Chris Tucker now

Close Runner Up:
Alicia Keys
Photo of them together:

Two years ago I would have said some dumb sh*t like Beyonce or Trina, but I think I'm thinking maturely and they just seem like dumb b*tches to me