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His Intercontinental title match with The British Bulldog at Summerslam 1992.
His Summerslam 1991 match with Mr. Perfect where he won the Intercontinental title, his first singles' title. Awesome in itself, but the match itself was also an extremely well-executed bout that served as a coming-out party for Bret. In Madison Square Garden, no less!
Summerslam 1994 saw him face his brother Owen Hart in a cage match that's still a fan favorite to this day (in a rematch from Wrestlemania X that's also a great match). Really, pick any Summerslam with Bret on the card and you'll probably see a good-to-great match from him.
The Wrestlemania X opener with Owen stood out as an outstanding matchup despite being on the same card as the famous ladder match between Razor Ramon and Shawn Michaels.
Bret shows up on WWE television on January 4th, 2010, for the first time in 12 years, to a hero's welcome. He promptly buries the hatchet with Shawn Michaels in one of the most fondly remembered segments in Raw history.
The reveal of his Batman Gambit against Vince McMahon on the 3/15/10 edition of Raw (baiting him into a no-DQ match before revealing he'd faked his injury), especially because of the coolly triumphant look on Bret's face after Vince realized he had been outsmarted.
How can anyone forget his Wrestlemania 13 match with Stone Cold Steve Austin, the match that ended with the iconic image of blood pouring down Austin's face as he refuses to tap to the Sharpshooter. It served as a double turn for Bret to heel and Austin as the white-hot face, and arguably kick started the WWE's Attitude Era.