Wouldn't you know who won the pony

Implies that the previously stated is rigged; local wrestling promoter, as told by Jim Cornette, gave away a pony to increase ticket sales and, to avoid losing money, rigged the raffle to ensure his son would win the pony

Of course, that asshole was late again!
Oh, wouldn't you know who won the pony!

Wouldn't you know who won the pony by Jack_Bongos January 15, 2020

i wouldn't be surprised if we never saw denise richards again 

A phrase so commonly used by Trixie Mattel, that it is canon now.

Jake: Yo dawg, where is that chick Denise Richards nowadays?
Logan: I wouldn't be surprised if we never saw Denise Richards again.

i wouldn't be surprised if we never saw denise richards again by Glass Half-Full August 29, 2021

I wouldn't piss on him if he was on fire

phrase describing a male person that you extremely dislike

My boss is a real asshole. I wouldn't piss on him if he was on fire.

I wouldn't piss on him if he was on fire by Studly Hungwell November 8, 2008

you would think so 

A phrase that is of literal agreement, but underlined with sarcasm. Particularly used when someone is extremely frustrated with something.

"What's wrong with this piece of shit?! When I push the power button it should turn on."
"You would think so."

you would think so by Skylak April 20, 2009

wouldn't've'e'er

A contraction of would not have ever

1. I wouldn't've'e'er creampied her if I knew she was going to get pregnant.

wouldn't've'e'er by Takamura_Drummer December 14, 2010

Wouldn't touch her with a 10 foot pole 

A female that is repulsively skanky/ugly.
Not only would you never sleep with her, being 10 feet away is still too close.

"I wouldn't touch that slut with a 10 foot pole, unless I was smashing her over the head with it."

Wouldn't touch her with a 10 foot pole by Diego November 12, 2003

I wouldn't piss up your ass if your guts were on fire. 

The ultimate FUCK YOU.
I would rather watch you die from internal hellfire, rather than extinguish your flaming innards with my urine.

Suzie: Hey man you are a fucking dick, why do you treat everyone like shit?

Balls Hampton: Fuck you bitch! I wouldn't piss up your ass if your guts were on fire.

Suzie: Weeps uncontrollably

I wouldn't piss up your ass if your guts were on fire. by GGR September 29, 2008