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orginated from THE BAY AREAS very own E-40, THE CALI KING OF SLANG!!! OH BOY MEANING EXPRESSION OF EXCITEMENT
phil: did you get saturday off work?
GuS: Please belive i did!
Phil: OH BOY!! We gonna do it real big then tonight!
oh boy by MackIn AZZ GuS August 5, 2004
To make a quick exclamation of joy and or shock. Generally a more laid back and sociable comment that derived from the early modern teens. Sister slang to "swell"
Jimmy: Hey Billy, you got a thing for Mary Jane?

Billy: You bet I do Jimmy, and Oh boy I cant wait to dive my large cock down her fuckin pussy, sure sounds swell!
oh boy by Fuck the punks! July 18, 2004
Phrase commonly used urban males anywhere West of NYC to indicate pleasant surprise and/or express admiration at a highlighted fact or situation.
1a. "You know Shalliqua and her crew gon' be at da club tonite, right?"
"Oh boy! We gon' pimp hard tonight on the real."

1b. "He put 22s on his Cadillac?! Oh boy!...It's on and poppin' now."
oh boy by redgyul September 22, 2004
certain male that a female talks about....usually cute funny sexy or all of these.
i was at da movies and oh boy tried to get with me.
oh boy by nic_nic October 3, 2004
A phrase that is repeated continuously every lesson by a devious maths teacher.
Class - "That number is actually a negative not a positive"

Timothy - "Oh boy!"
oh boy by Hero-2468 September 6, 2022

Oh boy!!! 

The loud, pumped up, excited phrase used when preferably giving daps or during an excited moment. Also used with the word Cruz or Miss Breau's niece's name. Created by Paul Gallo.
"Cruz......OH Boy!!!!"
"What up dog?.....(Dog)Oh boy!!"
Oh boy!!! by B-rad February 24, 2005