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1.
Phrase coined to describe the end of pro-wrestler Bret Hart's career. The end of the match between Shawn Michaels and Hart has become the most famous event in the history of the WWF/E.

Basically, Bret was going to leave the WWF in 1997. On November 9th, he was going to beat Shawn Michaels and then lose his final match by disqualification. Unfortunately, Vince McMahon decided to illegally call the match just as Shawn Michaels put Bret Hart in the famous sharpshooter move. Hart was most likely going to reverse this move and win the match, but McMahon decided to make Bret lose for whatever reason.

Bret was in shock and he spit on McMahon before leaving. He also expressed his anger by destroying a few TV cameras after the match.

During this era, Shawn Michaels was a member of a highly influential clique that often controlled the outcomes of various matches. Their power behind the scenes was linked to Vince McMahon and it led to the 'screwing over' of Bret "Hitman" Hart, a respectable, skilled wrestler.
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To this day, Shawn Michaels is hated in Canada (Hart's homeland) and the crowds often boo him or shout "You screwed Bret!" as a constant reminder of this unfortunate, unfair event.

The Montreal screwjob refers exclusively to the night of 11/9/97, but many comparisons are made to this famous match. The recent firing of Matt Hardy brought up a deluge of references to the untimely release of an excellent wrestler, Bret Hart.
Shawn Michaels is cool now but he most likely had a hand in destroying Hart's career in the WWF.
by anonymous June 03, 2005
 
2.
The Montreal Screwjob was the real life double-crossing of defending WWF Champion Bret Hart by Vince McMahon, the owner of the World Wrestling Federation (WWF), during the main event match of the professional wrestling pay-per-view event Survivor Series held on November 9, 1997 at the Molson Centre in Montreal, Quebec. A secret change of the match's pre-determined finish (known as a "screwjob" in professional wrestling parlance) was devised by McMahon and discussed with Hart's match opponent, Shawn Michaels. The plan was executed when the match referee, Earl Hebner, under orders from McMahon, called for the bell to ring and ended the match as Michaels held Hart in the Sharpshooter submission hold (Hart's signature finishing move), even though Hart had not submitted. Michaels was declared the victor by submission and crowned as the new WWF Champion, even as Hart and the audience demonstrated their outrage.

What if Bret screwed HBK in the Montreal Screwjob.
by Quentin M.Harris May 23, 2008
 
3.
Amy sexual act involving three different participants, where one of the three is duped or tricked into a compromising or embarrassing situation during climax by the other two people.
The two of us tied her up and banged her brains out. As soon as we finished we stole her wallet and peed in her purse. It was a real Montreal Screw Job.
by CHYNAisPretty June 01, 2012