Is this DOA by Bloodrock?
Fool in the Rain- Led Zepplin
AudreyK - The Night I Fell Asleep at the Wheel (or something like that) by the Bare Naked Ladies?
Yeesh!
“Tom Dooley” Kingston Trio
how quickly they forget…
This one is a hint to my previous selection, which has not yet been solved:
A wrestling tournament in which an extraordinarily small competitor, an extraordinarily immese competitor, a polygonal competitor, and a sad-sack competitor vie for victory.
hmm, I am tempted to say Particle Man by They Might Be Giants, but I am not convinced that is right.
A sensitive grunge rocker describes his codependant relationship with his wife.
Correct! My other tune is on the same album…
amarinth and Grelby, you got 'em. 
[sub]Actually, it’s Tonight Is The Night I Fell Asleep At The Wheel, which has got to be one of the longest song titles ever.[/sub]
Another one:
A romatic drifter bad-boy cowboy-type wants to die during his finest hour.
An idiot jock has sex with an allegedly lesbian girl, who proceeds to partially castrate him. He then becomes a gay sadomasochist.