Engaging in a frustrating pursuit that consumes more effort that it is worth. The idea is that "pissing upside down" is an ineffective way to do something very simple, and likely results in getting wet.

See Struggle-Bug
"I just wanted to get a quart of oil out of the garage but I bumped the boxes of scrapbooking supplies, which knocked over a bottle of brake fluid that split open and is getting everywhere. Now I'm pissing upside down."
by skippy123456 January 31, 2009
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raining so much it seems like all of the worlds water is coming down on top of you
"im not going out its pissing down"
by impartial annoymous November 26, 2003
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raining so much it seems as if an enormous elephant is pissing down on top of you
it was pissing down so much that i decided to stay at home
by afallengod May 27, 2009
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This phrase has absolutely nothing to do with getting drunk.

More accurately, 'pissing down the barrel', a phrase used by the British Army of the Napoleonic Era. Referring to the battlefield expedient of urinating down the barrel of a musket to clear black powder residue, when you didn't have the time or opportunity to clean it properly with clean water. The phrase became a way of referring to any action taken as an improvised expedient; then becoming a synonym for emergency or last-chance measures; and finally used to refer to any action that seems hopeless or with little chance of success.
"Dig in and hold them as long as you can."
"We may as well be pissing down a barrel."

"The approach will not be easy. You are required to manoeuvre straight down this trench and skim the surface to this point. The target area is only two meters wide. It's a small thermal exhaust port, right below the main port. The shaft leads directly to the reactor system. A precise hit will start a chain reaction which should destroy the station. Only a precise hit will set up a chain reaction. The shaft is ray-shielded, so you'll have to use proton torpedoes."
"That's impossible, even for a computer. It's like trying to piss down a barrel!"
by Ethdhelwen December 28, 2016
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chewing someone out; severe reprimand; the act of verbally punishing someone for a misdeed.
Because I did not finish the project on time, my boss spent half of the morning pissing down my leg.
by YONEIGHBOR November 11, 2009
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To make a simple mistake, a schoolboy error. Taken from the terrificly silly act one can undertake if one fails to lift the lavatory seat whilst relieving one's bladder.
ORTON "Dufresne, if you want to indulge this fantasy, that's your business. Don't make it mine. This meeting's over."

ANDY "Look, if it's the squeeze, don't worry. I'd never say what goes on in here. I'd be just as indictable as you for laundering the money!"

NORTON "Don't you ever mention money to me again, you sorry son of a bitch! You've really pissed with the seat down now Dufresne. Solitary! For a cocking month!"
by Otis P Jivefunk May 3, 2007
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