Winner: Justin Timberlake Need this even be explained? Post-Timberlake, Spears became an utter mess: the K-Fed marriage, the head shaving, the psychiatric hold, the paparazzi dating, the custodianship. An trying to make a comeback too soon didn't help her cause much either. Meanwhile, everybody loves the charming J.T. From his dating a cougar ( Cameron Diaz) to his Emmy-winning "SNL" appearances. Oh, and his music ain't half bad either.