Headless horseman

An alcoholic mixed drink invented in San Francisco which combines one part straight Jameson and one part straight Jack Daniels. "Headless" because you have to be stupid to order it and "horseman" because you need to be able to have the tolerance of a horse to drink it.

"Bartender, I'd like one headless horseman please"
"You seriously want me to mix jack Daniels and Jameson?"

by Halbert9000 September 8, 2017

Headless horseman

The result of someone getting their dick severed in the door of a Ford Mustang.

Watch out Jimmy! You almost shut your dick in the door and gave yourself a headless horseman!

by Moe Beer January 2, 2009

headless horseman

Fucking a girl while she's on top with a bag on her head.

I had to give these beat girl the ol' headless horseman cuz she was a butterface.

by Kyle June 15, 2004

The Headless Horseman

When a man cuts a jackolantern face in a pumpkin and jacks off into it

I heard Chris had fun on Halloween. He totally did the headless horseman to Mrs. Grossman's jackolantern.

by Dirrrrrrty Frrrrrreaks January 17, 2009

The Headless Horseman

The girl pulls shirt over her head with a cock in each hand

Heather decided to celebrate halloween by giving mike and mike the headless horseman

by mcj football sunday October 23, 2011

headless-horseman style

a method of dismembering in which a part of a whole is separated from its larger body in a manner that is especially clean and quick, leaving no remnant on the larger body except a clean slice.

Amy: Yesterday I drove too close to a construction barrier and ripped my passenger side mirror off.

Gary: Like clean off headless-horseman style or did it hang?

Amy: Clean off.

by wisler April 22, 2009

Headless horseman

Something that accidentally went free on November 15 2023

1: yoooo did you hear headless horseman was free?
2: really? I should have gotten it

by omgwhatiswhy November 17, 2023