That "Christmas Shoes" one - makes me want to give myself an insulin shot, and I'm not diabetic.
Oh gawd. And the movies/story too!
That song makes me think "Why are you giving them extra money for the shoes? Their MOM is DYING! She doesn't need shoes more than her kids need food does she?"
And yes, this was before and after my own mom died. i could understand the kids POV, but not why any adult would let them spend their much needed money on something that was so unnecisary. Just tell the little tykes that God will give their Mommy some shoes.

For worst songs, any song that is unnecisarrily sappy and depressing. Either of those are fine in moderation alone, but never together.
Also, any song with a hastily added on war or patriotic refrence tacked on so it'll sell more. I support our troops, but am saddened when someone tried to make a buck off tragedy or someone else's hard work. To me this comes down to "All hat, No cowboy" (Although oddly, Toby Keith songs don't bug me, and I love the song "riding with private malone" No clue why those two don't bother me.)