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Hilarifying 

1) An absolutely horrifying situation that one still finds hilarious.
a) I can't believe Bill just shit his pants in the middle of dinner with his boss and continued to eat like nothing happened. That's hilarifying.

b) Did you see the last Southpark Episode where Timmy the cripple fights Jimmy. That was hilarifying!
Hilarifying by Shibby! February 12, 2008
Related Words

Hilarifying 

A situation or sequence of events that is hilariously strange, yet absolutely terrifying.
"Jeremy, get out here! Jim is being molested by a grizzly bear and a gorilla in drag at the same time, it's hilarifying!"

Hilariating 

when you hate that something is so hilarious!!! ; So funny that it is gut busting...can't stop laughing and you hate it because it hurts.

Hilariating, hilariater
Pooder is hilariating why are you ripping on that person so bad!!!! Stop!!!! She is going to bust her gut! <3
Hilariating by namedropper77 January 3, 2010

hilarifying 

Concurrently, hilarious and horrifying...
Because separating those two concepts with the word 'and' is simply too far apart.
If Trump wasn't dangerously terrible, he would be merely hilarifying.