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Word Up!: Original artist Cameo, cover by Gun. The original version was (IMHO) quite lame but then comes a rock band from Glasgow (Gun) and makes a total mindbogglingly kick-ass version of it! Korn also made a version of it with a really cool video but musically quite boring.
Original: http://www.youtube.com/watch?v=EV4L0L4sAQo
Cover: http://www.youtube.com/watch?v=1xARbuaOy7c&feature=related
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Next is Nirvanas Smells Like Teen Spirit which needs no presentation. Unfortunately too many people have butchered this song with pretentious crap versions (like Tori Amos) so it takes a lot to make it interesting again. This version is performed by Steve Earl (banjo) and Patti Smith. Their version blows me away, it's mellow but still very very intense, they totally made it their own:
Cover: http://www.youtube.com/watch?v=QwpLqrh19Ws&feature=related
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Finally we have Johnny Cash doing a cover of Hurt by Trent Reznor (Nine Inch Nails) from the Downward Spiral album (94). Johnny Cash made a cover of it on his "American IV: The Man Comes Around " album. Both versions are awesome and the form quite similar; naked, accoustic and with the lyrics in focus but in my opinion Cash stole it from Trent just like someone steals your girlfriend. Note that Cash changed the line "crown of bleep" to "crown of thorns"
Original: http://www.youtube.com/watch?v=gjwgYvzQWS4
Cover: http://www.youtube.com/watch?v=SmVAWKfJ4Go
