"Ugliest Girl in the World" is the first song on the second side of Down In The Groove
. It's also one of the album's two collaborations between Dylan and Grateful Dead lyricist Robert Hunter, the other being "Silvio."
Both Hunter and Dylan are known for layers of poetic complexity in their lyrics, but with "Ugliest Girl in the World," it's safe to say that it's just for fun. The song comically describes an outlandishly unattractive woman, with each verse punctuated by a sincere declaration of love for her.
She's got a hook in her nose. Her eyebrows meet. She's got two flat feet and snores in bed. Still, though, Dylan is hopelessly in love with this, the ugliest girl in the world. In that way, it's similar to Dylan's "God Knows
," released in 1990 on Under the Red Sky
. That one opens with the lines: God knows you ain't pretty
God knows it's true
God knows there ain't anybody
Ever gonna take the place of you
The likeness ends there, though. At least, it appears to, as "God Knows" is unambiguously spiritual/religious.