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1.
Anytime a person utters the phrase "Would you rather" usually followed by two horrible sexual situations in which no person would want to partake in either. Usually one of the situations involves sex with Jimmy. Usually only used by homosexuals and men with tiny penises.
We were walking to class when Isaac used a Jimmyism, "Schuh, would you rather let me stick it in your ass, or let 40 black men rape you in the ass at the same time?"
by Istoll January 31, 2007
 
2.
1. (noun) A configuration which does not exist on a server or network infrastructure after a reboot or power down / up; a configuration that was never permanently saved.

2. (noun) A configuration that is so complex or abstract that only the creator can decipher it. See Also: enigma
1.
Tech One: I rebooted the firewall last night...
Tech Two: So?
Tech One: It didn't have any routes when it came back up.
Tech Two: LOL. You've been hit by a Jimmyism.

2.
Tech One: Did you look at that config?
Tech Two: Yup.
Tech One: Did you understand it?
Tech Two: Absolutely not.
Tech One: I guess it's a Jimmyism.
by Slite September 19, 2006