Crowning Moment of Awesome: While Bret Hart would get the gold at the end of Wrestlemania 10, Owen Hart would get the greater glory - in the show's opening match, he beat Bret in what's considered one of the best matches for either Hart brother.
His match with the Hart Foundation against Stone Cold Steve Austin, the Legion of Doom, Goldust, and Ken Shamrock at the Canadian Stampede PPV. Despite being the heels in the US after Wrestlemania XIII, the Harts were hugely over in Canada. A great match, it's Owen, not Bret, that gets the roll-up on Austin and wins the match in front a white-hot Calgary crowd and the whole extended Hart family.
Crowning Moment of Funny: Read Mick Foley's first book and you'll get a treasure trove of CMOF's concerning Owen. One of the funnier ones being the "popcorn bag" match between Foley and Owen whose sole purpose was to make Stone Cold Steve Austin break character and laugh at ringside. It worked. Austin's response? "You two are the shits."
Dude, Not Funny: To this day, making fun of Owen's fatal accident is just something you don't do unless you want all of the internet yelling this at you.
Fridge Horror: Owen Hart's theme, Enough is Enough when he was with the Nation, or the Blackhart theme. In the song, it has Owen Hart shouting quotes. He is in character, but consider the following:
"Come and take your best shot": Many critics thought the death was fake, and criticized the WWF for it.
"I tried to be a nice guy": He stuck with his contract, he did everything that Vince McMahon (the Chairman), the writers, and bookers said. Owen was convinced by the crew that the zip-line was safe. He, being an incredible man, believed it.
"I played by the rules": Supports the last quote.
"You turned your backs on me": Possibly the WWF doing the show after his tragic fall.
"I snapped": The cable snapped and this is what killed him. You could also view this as him making the decision to hang on the zip-line, being crazy enough to do such a thing.
"I was a victim": Death.
"Enough is Enough, and it's time for a change": Owen Hart isn't in the Hall of Fame yet, his widow, Martha Hart will not allow it.
Go back and watch Over The Edge. The opening monologue by The Undertaker is this. Especially considering how he's talking about "Your Heroes will fall" and all.
Tear Jerker: His death at Over the Edge, as well as the RAW paying tribute to him the following night.