An old hare hoar,
And an old hare hoar,
Is very good meat in Lent
But a hare that is hoar
Is too much for a score
When it hoars ere it be spent.
My mistress’ eyes are nothing like the sun;
Coral is far more red than her lips’ red;
If snow be white, why then her breasts are dun;
If hairs be wires, black wires grow on her head.
I have seen roses damasked, red and white,
But no such roses see I in her cheeks;
And in some perfumes is there more delight
Than in the breath that from my mistress reeks.
I love to hear her speak, yet well I know
That music hath a far more pleasing sound;
I grant I never saw a goddess go;
My mistress when she walks treads on the ground.
And yet, by heaven, I think my love as rare
As any she belied with false compare.
Gram Parsons: She
but he didn’t mind if she wasn’t very pretty
for deep inside his heart he knew she was the only one
ooh, but she sure could sing
I came in here to say this, and there’s no supposedly about it - Leonard Cohen describes writing it about Janice Joplin when he performs it live. 
Nobody can touch Mike Smith’s performance of this song (it’s my favorite DC5 record), but just so you know, it was first recorded in 1959 by Marv Johnson.
My entry in the sweepstakes is The Lovin’ Spoonful’s Bald Headed Lena. (I don’t know if it’s their song or a cover.)
Bald Headed Lena
Has anybody seen her
Cute as she can be
She’s got a cue ball head
That’s hard as lead
But she’s all right with me
The Lonely Island - “Dream Girl” (Brought to you by Chex Mix)
“Dream girl you amaze me, all dressed in paisley
Love how not one but both eyes are lazy
When I first saw you you were drivin’ the bus
Thick skin, strong nose like a rhinoceros”
Joe Tex Skinny Legs and All
Louis Jordan- You’re My Meat.
A flashback from my childhood - The Banana Splits Two Ton Tessie
Huggin’ and Chalkin’, Hoagy Carmichael: about how great it is to have a fat woman, and how you need a piece of chalk so you can tell where you began huggin’ her.
Your Feet’s Too Big, Fats Waller
“She’s got freckles on her BUT: she’s nice.”
Let’s Do Something Cheap and Superficial, Burt Reynolds
Big Boned Girl - k.d.lang
Big Legged Woman - Jerry Lee Lewis
Not sure she’s an object of affection…
Is this a whoosh?
I thought it was common knowledge that Lola wasn’t a she.
Kevin ‘Bloody’ Wilson - She’s The Sorta Sheila - NSFW
Solomon Burke’s “Uptight Good Woman” is about an ideal woman, not someone specific, but it contains the line:
Now she don’t have a lot of pretty clothes
and a pretty face
Just two loving arms
to keep warm and safe
The Crystals’ “He’s Sure the Boy I Love”
He doesn’t look like a movie star
He doesn’t drive a Cadillac car
He’s sure ain’t the boy I’d been dreaming of
But he’s sure the boy I love
No, a fat bottom is good.
Has no one yet mentioned My Guy by Mary Wells?
No muscle bound man
Could take my hand
From my guy.
No handsome face
Could ever take the place
Of my guy
I’m also rather fond of I Go For That by Audrey Morris, in the “My Funny Valentine” vein:
Your kiss just misses,
Your dancing is rough,
But I like that stuff,
I guess I don’t get around quite enough!
And of course there’s Tom Lehrer’s My Girl…
Gilbert and Sullivan, the Judge’s Song from Trial by Jury
Lyle Lovett - She’s Hot to Go
Well I could handle it behind her
And I like it on the side
But don’t make me look around her man 'cause she’s
Ugly-ugly-ugly-ugly-ugly