LoL, Beren, I love the "Time of Your Life" idea!
Okay, how about
-"Down" by Fuel for Gollum? Really Sméagol to Gollum..."I know you want me to love you/All you ever do is bring me down/Won't you go away forever..." Of course, that last line clinched it for me.
-"Last Time" also by Fuel for Frodo. I can't really point out any particular lyrics, the whole song really fits him as he relates to the Ring..."I'm not the first you sucked down," etc. He keeps promising himself that "this is the last time," as in the last time he uses the Ring.
-If you change the pronouns around a little bit, the chorus of "Bad Day" by Fuel (I got "Something Like Human" for Christmas, so sue me) rather fits Sam and Frodo, as narrated by Sam.
-In addition to "Hey, Ho, to the Bottle I Go" can you imagine "Closing Time" by Semisonic at the Green Dragon?
~*~Orual~*~
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"Oh, my god! I care so little, I almost passed out!" --Dr. Cox, "Scrubs"
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