Just last year, Emma Stone starred as Cruella, of 101 Dalmatians fame, for starters. But also for instance Jesus Christ Superstar, the musical/movie from the 70s that depicts Judas Iscariot as the sensible, level-headed guy who wants to protect Jesus more than he wants to hurt him. Or all sorts of books or shows with vampires or other monsters as main characters instead of baddies, including kid's movies like Shrek or Monsters Inc.

Or even, though I may be taking it a bit far, Milton's Paradise Lost, which has often been described as depicting Satan as more sympathetic than Jesus/God. Certainly he's more interesting to readers today, however Milton intended it at the time. Though your man CS Lewis strongly argued against that view, as I just learned from Wikipedia...

Sounds interesting!