Raymond Reddington (played by James Spader) in "The Blacklist." He's an internationally wanted criminal with smirking overconfidence made only slightly less offensive by the fact that he's usually right. In real life he'd be intolerable. In a TV show he's extremely entertaining.
Pretty in Pink (1986) - James Spader
James Spader Supernova. Yea, this was James only 16 years ago!!!!