I heard it came from the cops in the early 20th Century-probably the 1920s-chasing the hookers off of 23rd Street in New York City and not catching them, thus the hookers gave the cops the "23 skidoo."
That bitch gave me the 23 skidoo!!!!
We better 23 skidoo!
They gave me the ol' 23 skidoo!!
She tried to give me the ol' 23 skidoo but I caught her!
Bums would sleep around 23rd St and when the cops came along they would hit them with their billy clubs and say "23 skidoo."
My grandfather was a cop down there around 1920 and told me how this term came about.
Smoker: Well, we gotta 23 skidoo!
Evidence of the 23 skidoo has long been lost and only skilled historians have managed to keep its intellect savvy.
Criminal about to be executed: "23 skidoo!"
Executioner person: "Shit. I guess we'll have to let the rapist/murderer free on the account of his supreme 23 skidoo."
George Bush, 2003: "23 skidoo."
World: "I guess we'll have to continue acting like blubbering idiots at such well-spoken doctrine and reelect this shithead."
Yes, an STD. (generally chlamidiya, gonnorhea, something that can be treated with penicillin or Cipro).
This phrase was used a lot in the circles I hung out with in the late 80's/early 90's.
Thomas: "Dude, that sux you didn't get any, but it beats going to the doctor."
Keith: "Yeah, I did her a week ago, and I had to go to the doctor today to get rid of the 23 skidoo she gave me. Fuckin' whore!"
Thomas: "Shit, that sux man. I won't tell anyone." "HEY, MIKE! KEITH GOT THE 23 SKIDOO FROM DONNA!!!"