an expression used when completely at a loss of words to say, or when there is a lull in any conversation.
"Jacob" is on a date with "Jane"...
jacob: *points at girl at the bar.* oh my god, look at her. she looks pathetic.

Jane: um, that's my friend!
***awkward silence***
Jacob: Holy Barrel of Monkeys!
by Almost Urgent July 14, 2009
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Surgically removing the top of a beer can (preferably a Natty Ice) with a can opener so an individual will be able to expose themself to maximum beer chugging capability.
Male 1: I don't have the steady hands or the technology to chug this beer.

Male 2: Don't be a vagine, get a can opener and turn that can into a monkey barrel.
by Dikembe Fratumbo January 27, 2011
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Utterly and completely worthless; completely valueless.
Bubba: That is about the stupidest fucker I've ever met.

Rawhyde: You said it, brother. He's as worthless as a barrel of monkey nuts!
by Rawhyde & Bubba May 31, 2007
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This term is used as sarcastic description of something not being very much fun. A barrel of monkeys are actually little plastic monkeys, and their arms can loop together to make a chain. In other words, not very fun.
by dudefromSD November 28, 2007
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When a group of men stand in a circle to jerk each other off, you stroke the guy to the right while cupping the guy to the left of you, therefore your arms are bent like that of a plastic monkey from barrell full of monkeys
Dude, you know frat boys sit around jerking one another looking like a barrell full of monkeys
by toadpuss May 23, 2011
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a very good time(from the the name of a toy consisting of a plastic barrel filled with flat plastic monkeys that can be hung by each others curved arms)
That dance was more fun than a barrel of monkeys
by The Return of Light Joker November 18, 2007
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