Do you mean the song he sings when Drillbit is on his date? It's Enrique Iglesias - Hero
But I can't remember anything else :P
It is All Along The Watchtower
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Rachel patten and taylor swift
Taylor Swift - WRONG ! its actually Shiloh that sings it :)
Sounds like Zach Braff to me.
Dire Straits Taylor Swift - Love Story
Livingston Taylor