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<Verb> The act of blowing a joke or a rip, usually by sputtering out sentence fragments or by stuttering. This usually leads to laughter by one's friends and extreme embarrassment to the person who 'derailed.' The offender will stay very quiet for a long period of time following one of these outbursts.
"Man, you're so stupid when god handed out brains you thought he said trains...and you went...and got on...and went for a ride...wait....goddammit!!!"

"HAHAHAHAHAHAHAHAHA HOLY SHIT, you're retarded!! Nice derail, Jay!!"
Derail by Jamon26 February 16, 2010
The act of passing gas on an up escalator, while inadvertently (or purposely) farting in everyone else's face who is behind.
I totally derailed some people at the galleria today!
Derail by darthxduder November 22, 2013
To move from the pink, to the brown, when making the sweet sweet sechzor.

Or if you'd like it a bit clearer:

To go from vaginal to anal intercourse
Man A: Dude, I tried something new with my girl last night.
Man B: Oh yeah, what's that then?
Man A: Well, I went from pink to brown.
Man B: Oh...you derailed!! Fair play matey.
derail by Sid P July 10, 2007
To derail someone means while having sex you slide up off the penis that is placed somwhere inside the your body.
I was getting slammed and was tired so I derailed with no hands and went to bed.
Derail by Ayy Finn November 6, 2010

Derail your corntrain 

An expression used to describe someone trying to fuck you in the ass, whether physically, personally or financially.
The car salesman was trying to sell me an air conditioned glove box, extended warranty and undercoating. I said hey buddy, "Stop trying to derail my corntrain"
Derail your corntrain by Matt September 1, 2004

derail the gravy train

A phrase, meaning to obstruct the flow of money.
some bitch: You ran your mouth to your parents, and now your living in a camper. You sure know how derail the gravy train.

some dude: I don't care if they own estates in Europe, the West Indies and America. I do miss my Ferrari Enzo, though.

derail people 

derail people are people, who study mechanical engineering at Karlsruher Institut für Technologie and are used to test the newest rollercoasters at Europa Park. In Fact they are just invited to die.
Are you one of those derail people?
You have to study mechanical engineering at KIT to become a derail people!
I was once a derail people - Markus Enger RIP 2019
derail people by SadNiggaDerailer January 4, 2019