Well, I'd give Stan Rogers the nod for "First Christmas Away From Home"--which he mercifully hardly ever performed. Kind of an anti-Christmas song, I think the cheeriest line is: "At least it means no beating from her dad..."Talk about cheap emotional manipulation! At least with "Yeastcake Jones", mentioned above, he had the excuse that he didn't write it, and that album was for the family, not for us.
The really greatest songwriters seem to be able to come up with the worst songs, sometimes... Willie-O