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.
"Dude, how was your grandma's house?"
"It was a barrel full of monkeys"
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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