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the longest yard 

1. An American sports comedy movie from 1974, The Longest Yard, tells the story of an incarcerated former professional American football player who builds a football team from the motley crew of the other prisoners. This team is supposed to play against the guards, who use their position, dirty tricks, and foul play to hinder the prisoners' team. The movie has had many remakes, most notably a 2005 one starring Adam Sandler.

2. A challenge that is greater than expected or reasonable. It comes from the title of the movie, where the prisoners have to not only get better at football, but also overcome inexperience, low confidence, lack of equipment, officers' cowardly attacks, etc. In gridiron football, a team advances score by walking yards until reaching the endzone. Since the prisoners have to deal with much more problems than the opposing teams, these yards are way harder for them to get, i.e., they are "longer," not in size, but in effort.
1. You like football, prison shows and comedy, you should watch The Longest Yard.

2. To overcome addiction and homelessness was the greatest yard in his life.
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the longest yard 

The act of pleasing yourself through anal penetration, the teasing of your scrotum, and the sucking of your toes all at once.
I got bored last not so I locked the door drew the blinds and attempted the longest yard.

sans sheriff 

Lawless use of fonts or typography, with no regard to aesthetics or legibility
I'm putting this CV straight in the bin. Written totally sans sheriff.
sans sheriff by Jamarley July 3, 2019

Breadhead 

Someone who is addicted to obtaining money and building wealth. A money addict and fanatic. Breadheads often work more than one full-time job, and some even participate in illicit activities to "obtain the bread".
A breadhead is like a crackhead, but for money instead of crack.
Breadhead by 🅱️ U S 3 4 8 March 30, 2022

Stink lines

As seen in illustrations or cartoons: Wavy, vertical lines rising above a person, place or thing. Denotes a foul odor.
"You didn't put enough stink lines on your picture of the teacher."
Stink lines by Athene Airheart March 14, 2004

schmegegge 

Yiddish slang word meaning bullshit, baloney, hogwash, nonsense, crock of shit or hot air.
I don't buy the schmegegge about Morty sleeping with Moira.
His version of the story was pure schmegegge.
The whole schmegegge was made up to get Liz a little bit of attention.
schmegegge by budsbabe February 1, 2008

eye bleach 

Looking or experiencing something nice after witnessing something horrid like a disgusting gif or a disturbing video. Typically used as eye bleach are nice images of whatever makes the disturbed person happy.
"Bleach my eyes! Why is that woman's face ripped off!?"
*Looks up images of puppies and kittens.*
"That's good eye bleach."
eye bleach by Rini2012 November 29, 2016