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1.
Nickname for Pittsburgh Penguins forward GARY ROBERTS, who is just plain bad ass 24/7, even at 42 years of age.
Scary Gary will end the Ottawa Senators playoff run... again.

Scary Gary beat the shit out of Ben Eager, who is young enough to be his son... BAD ASS!
by McLovin' April 12, 2008
 
2.
sticking pinky finger up your partner's butthole
when your partner during sexual intercouse (sex) sticks their pinky up your bum hole it is called a "scary gary"
by BA BullDawg October 18, 2010
 
3.
Gary, Indiana. Referring to the more crime-ridden areas downtown near Indiana Harbor. Gary once held the distinction of being the murder capitol of the nation.
Don't go out at night in scary Gary.
by Bribru June 13, 2007
 
4.
When the shady awkward asian kid at the party ends up raping the passed out drunk girl by the end or even middle of the night depending on ms "I can drink more than any dude here's!" tolerance level.
Hey man, are we talking about Gary, or "scary gary?"
by acid$reign February 16, 2011
 
5.
The weird guy that lives next door
Scary Gary's sunbathing nude on the roof again
by Rick Hickson August 22, 2004