Well, he says in a later email:

You have made a sort of 'joke' song work, tho: I think Lady Luck is a great song. It is not a serious song, but it COULD be, it has a powerful emotional resonance other than being just 'funny.' That's why I can listen to Lady Luck 2,000 times and still think its a good song.

So he likes there to be a little more going on than just humor. I think that it probably is more a question of taste than anything else, and my tolerance for songs that are just out and out goofy is a lot higher than his, I think, but I try to respect that when I pick out songs to bring to him.

Here's Lady Luck, by the way: http://killdevils.com/demo/LadyLuck.mp3