29. Eminem f/ Dido "Stan" (2000)
Director: Philip Atwell, Dr. Dre
Album: The Marshall Mathers LP
They did a bang up job of making actor Devon Sawa (aka "Stan") look like a total psycho slash Eminem clone in this video. Dido's on the hook to the song (it was her song first, after all) and she makes a guest appearance in the video as the pregnant girlfriend of Stan. The video shows the twisted effects of fanatical behavior, as Stan bleaches his hair like Eminem, then writes a letter to him. He puts Dido gagged in the trunk of his car and drives it off a cliff into a river. It's dark and morbid, and totally appropriate for the track.