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homelesser

not homeless, it is more homeless than homeless, complete utter poverty and worthlessness, zero self worth
Me: Hey dude did you see that kid Tyler?
Jon: HAHAHA, ya he's so homelesser than Bill Cosby!!!
Me: Oh JON! HAHAHA!
homelesser by jon1232 March 5, 2018

homelessly 

The girl is so busted, she is homelessly.
homelessly by justagoodguy November 4, 2006

Homelessey

To have a similar appearance of a homeless person or reprobate.
He was looking rather 'homelessey' today.
Homelessey by indieboysf July 13, 2010

homelesserotic

It's totally homelesserotic when you're having sex with a random girl and she screams out, "do you have any spare change!?!" and you finish
homelesserotic by magnum-man September 29, 2012

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