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

With a very effective gut-punch at the end.

She’s Just My Style” by Gary Lewis & the Playboys?

“Other guys who meet her, they don’t think she’s much to see
I can’t even tell you what she always does to me”

Then there are a variety of songs that appear to be about women who perhaps do not fit the ideal of conventional beauty, such as:

Short Fat Fanny
Skinny Minnie
Boney Moronie

Jimmy Murphy’s “Put Some Meat on Them Bones

I once heard a bluegrass tune with the chorus:

Always marry an ugly girl.
That’s my favorite kind.
She’ll never ever leave you
but if she does you won’t mind.

U Stink But I Love U– Billy and the Boingers

Lyle Lovett - She’s Hot to Go

Stay With Me - Rod Stewart
Won’t need too much persuading
I don’t mean to sound degrading
But with a face like that
You got nothing to laugh about

Funny Honey from Chicago, though it’s meant ironically.

Lola perhaps? At the very least she walked like a woman and talked like a man which doesn’t sound all that great honestly.

Crank it up, somewhat…

A Better Place To Be, Harry Chapin

““I wish that I was beautiful, or you were half way blind.
And I wish I wern’t so dog gone fat, and I wish that you were mine.”

Martin Mull’s “(How Could I Not Miss) A Girl Your Size.” As a bonus, both the singer and his love are obese.

Mail order Annie - Harry Chapin
You know you’re not as pretty as I dreamed you’d be,
But then I’m not no handsome fancy Dan.
And out here looks are really not important.
It’s what’s inside a woman when she’s up against the land.

“Bill” from Showboat:
And I can’t explain,
It’s surely not his brain
That makes me thrill -
I love him because he’s wonderful,
Because he’s just my Bill.

Someone (I think it was Barbra Streisand) sang this to President Clinton and when I saw the clip, I thought, “Didn’t anybody think about the lyrics?”

A song about a skinny, bald woman.

BABALU’S WEDDING DAY
Featuring “husky Babalina”

He met his woman at a baseball game
Playing second base for the Milwaukee Braves
Husky Babalina was her name
Asked her for an autograph and made a date
Babalu, Babalu, Babalu’s wedding day

If we broaden the criteria to unconventionally attractive, I’d nominate “Dare To Be Fat” by Rootboy Slim.

“That’s okay, I’m portly too.”

Billy Joel “I Love You Just the Way You Are.”

*I don’t want clever conversation
I never want to work that hard
I just want someone that I can talk to
I want you just the way you are. *

Your clothes are crap, your hair is ugly, but at least you’re stupid. (sigh) SO romantic!

Rod Stewart also has “Maggie May”:

The morning sun when it’s in your face really shows your age
But that don’t worry me none in my eyes you’re everything

Nice Legs, Shame About Her Face by The Monks

“Baldhead” by Professor Longhair (Roy BYrd) “Oh looky there she ain’t got no hair.”