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the crookedest street in the World 

Lombard St. in San Francisco, California, USA. It's a 1~way downhill steep street with many switchbacks, is lined by several homes, the speed limit is 5 MPH & it goes from Van Ness to Leavenworth. The views are outstanding!
You won't believe this but I accidentally drove down the crookedest street in the World & didn't find out it was that street until a month later! I swore I'd never drive it again but a week later I did. The views are phenomenal.
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Crooked Serbian 

When you're fingering a girl and break your finger inside of her.
"Hey Dusan, what happened with you and the girl last night? Why is she complaining about her ruptured vagina?"

"Man, I gave her a Crooked Serbian. I have to see a radiologist today."
Crooked Serbian by Tricycle January 23, 2013

Hit a straight lick with a crooked stick 

Overcoming incredible difficulties and doing remarkable things.
Ex: When a kid grows up in a bad situation without any guidance, but somehow rises above it and has a successful life; that kid hit a straight lick with a crooked stick.
The best, most epic minecraft Youtuber ever.
With swag gamer epic skills and is generally just really cool epic gamer swag.
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Man, have you seen the latest Cronkers video?
Cronkers by Cronkers February 12, 2020

crooked as a Florida election 

Inspired by the incompetence and blatant corruption, often both at the same time, seen in Florida elections since the year 2000.
Our city council is as crooked as a Florida election.

crooked head syndrome

When an individual develops a slight curve in his or her neck making it appear the head is crooked. May progressively get worse until head is parallel to the ground. Usually making an individual less attractive. Depression often pairs with crooked head syndrome.
Look at that girl she has crooked head syndrome.

Missy has severe crooked head syndrome.
crooked head syndrome by Craigadon September 15, 2009

Crooked grind 

A skateboarding trick where you ollie onto a rail, land your front truck on the rail, and grind the rail at about a 45 degree angle. Not a beginner trick.
Crooked's look neat.
Crooked grind by Ricky Benda May 27, 2005