Songs where the object of affection is NOT attractive...

Fat by The Violent Femmes sort of qualifies. He’s hoping she gets unattractive.

Since I linked Big Legged Woman, this seems only fair…

Skinny Legs and All - Joe Tex

Wouldja believe that tune goes back to 1938? Here’s Mildred Bailey singing it with the Red Norvo band.

Going back to 1931, you have a British hit, *Miss Elizabeth Brown.

Tho’ I know she doesn’t look like beauties in a picture book
I’ll be broken hearted if she turns me down
Her father is a millionaire, he hasn’t got a son and heir
That’s why I want a love affair with Miss Elizabeth Brown*

Al Bowlly, Britain’s crooner of the day, sings it here, along with a bunch of his other platters.

Rosie by Jackson Browne? :smiley:

I also wanted to add Cholly by Fishbone

“I love you Cholly with your big fat body/ Oh golly Cholly you’re just chubbly wubbly wobbly”