5. John Ritter - Wholly Moses! (1980)
This is one of my favorite Devils. Satan (played by the late, great John Ritter) meets up with Herschel (Dudley Moore) outside of Sodom and Gomorrah (or some other city; I can't remember right now) after God destroys those wicked cities. Ritter plays his Devil as a disillusioned former partner of God who is embittered by God taking credit for Satan's ideas. Even Ritter's wardrobe is hilarious. An obvious Halloween costume, the cheesiness of this ensemble perfectly matches the tone and attitude of Satan in Wholly Moses!.
Weird or Wonderful? - Weird. With lines such as "Trees...my idea", Ritter cracks me up every time I see this movie.
4. Jack Nicholson - The Witches of Eastwick (1987)
The small and somewhat repressive New England town of Eastwick is the setting for an unusual story about Satan and his wiles. Three previously-married women (played by Cher, Susan Sarandon, and Michelle Pfeiffer) continually lament the availability of suitable male companionship. After one particularly powerful lamenting session, Satan comes to town in the form of Daryl Van Horne - a man so disgusting and so vulgar it would seem he couldn't seduce a rubber sex doll, yet he proceeds to have his way with each of the three friends, who seem to blossom from the experience. Eventually they figure out what's going on and attempt to remove the Devil from their lives.
Weird or Wonderful? - Wonderful. Nicholson is so thoroughly repulsive in the first part of the movie and so thoroughly evil at the end that it's hard to believe he's playing the same character. That may sound like the recipe for a bad performance, but it's not.