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wouldn't you know who won the pony

refers to the story told by Jim Cornette when a local wrestling promoter , faced with declining attendance , rigged a lottery to give a way a pony so his son won it , so we did not lose money on the deal . As a result anything is is obviously rigged is referred to as wouldn't you know who won the pony .
Billy got picked to be hall monitor again .
Well Wouldn't you know who won the pony
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Even I don’t know who to root for

What you say when caught in the middle between 2 of your enemies/unpleasant problems personified as people

When you don’t know what’s worse or better in a situation determinate of 2 or more parties
*uncle and stepdad fighting over who’s going to Molest the 14 yr old daughter

Daughter: tf ?

God: even i don’t know who to root for

Do you know who else has dementia? 

Do you know who else has dementia? Do you know who else has dementia? Do you know who else has dementia? Do you know who else has dementia? Do you know who else has dementia? Do you know who else has dementia?
Do you know who else has dementia?

Do you know who else has dementia?

Do you know who I am? 

A line often uttered by self-absorbed asshats who feel they are being wronged by someone in a particular situation. History often proves that these douchebags, who might have an extremely low level of fame that most people are unaware of, are being treated on equal footing with the rest of the general public. This angers them even more.
BOUNCER: You're going to have to leave this club, sir.

DOUCHE: Wait a minute, wait a minute...do you know who I am?

BOUNCER: No. Get the fuck out of my face.

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!

You-Know-Who 

The name in the Harry Potter wizarding world for Lord Voldemort. He has also been called "He Who Must Not Be Named", "Lord Thingy", and other appellations of the sort.
Ron: "Hey, Hermione, I heard that You-Know-Who is trying to find Harry. D'you think he wants to kill him?"
You-Know-Who by Lizzi K April 21, 2006

You-Know-Who 

A person, usually an acquaintance, who you find completely detestable. The mere mention of their name is enough to fill you with a feeling of dread, while an encounter with this person inevitably leaves a cloud of misery hanging over an otherwise pleasant day. This term is derived from a common reference to Lord Voldemort from J.K. Rowling's Harry Potter series.
"I bumped into You-Know-Who the other day...that basically ruined my week."
You-Know-Who by Bumpalicious February 6, 2010