The longest match in Smackdown history was an Ironman match between Brock Lesnar and Kurt Angle on September 18, 2003. Angle was the babyface WWE Champion while Lesnar was the heel challenger. They had a number of matches already that year. All of them were great. This one was on another level because they had to go an hour. Even with all the commercial breaks in the match, it's still the best Smackdown match ever and one of the best matches in either man's career. Lesnar was the aggressive heel that was able to jump out to an early lead. Thats the right way to do it since faces are better when theyre the underdogs that are trying to fight back. There was a really cool spot early in the match when Lesnar intentionally disqualified himself and then he hit the F5 soon after to tie it up 1-1. With Angle weakened, Lesnar went up 3-1 after a countout for a fall and then making Angle tap out to his own Ankle Lock. Good booking! Angle cut it to 3-2 after an Angle Slam for a fall. https://www.youtube.com/watch?v=OqhvCgGXDNE Lesnar built it up to 5-2 heading into the final 20 minutes, so Angle needed to get on fire in order to catch up. The last three minutes were insane with Angle down 5-4 and trying everything he could to come back. Angle applied the Ankle Lock again with about 15 seconds left. Lesnar was close to tapping out, but he withstood the pain and held on until the buzzer, so Lesnar left with the WWE Title. An hour long match is a lot longer than a "moment" of course, but in terms of greatness it belongs in the discussion with every other awesome thing that has ever happened on Smackdown. What a phenomenal match this was.
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