My vote for prettiest TW song is Cold Cold Ground, but I love this song. I clicked on this very cautiously: there's this weird pattern of celebrity deaths coming in 3's. Tom Waits still walks among us.
I've got pretty mixed feelings on Tom Waits but this is a good one. I'd probably vote for anything on The black Rider as my favorite though, sine he didn't write any of the lyrics and his lyrics are the thing that sometimes puts me off. they alternate between really good and painfully maudlin, sometimes in the same song. When he's on he's really on, though.
My parents would always listen to Tom Waits when I was a little kid (Mostly Rain Dogs) and they also had those old Sesame Street records.. since I wasn't really listening to the lyrics I always thought they were playing Cookie Monster songs at BBQs and stuff, maybe just for me and the other kids.