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Even though I don't like Shawn Michaels (I'm a huge Bret fan), I can't deny how legendary his accomplishments are. Here are the 10 most significant matches/moments of his career that I remember.

1. Marty Janetty barbershop incident
2. Beating Bulldog for first single title (he was being held back until this)
3. Razor Ramon ladder match Wrestlemania X (showed his talents were rare)
4. Winning 1995 Royal Rumble (moved from midcarder to main eventer)
5. Undertaker Hell In a Cell match (simply a fantastic performance; one of the first major moments in the Attitude era)
6. Montreal Screw Job (cast a shadow over his accomplishments, unfairly somewhat)
7. Dropping title to Steve Austin (did the right thing for business, and was the last time we'd see the young Shawn)
8. Winning WHC at Survivor Series 2002 (the moment you never thought you'd see)
9. Ending Ric Flair's WWE career (respect by and for other greats)
10. Undertaker WM25 match (showed he was still the biggest show-stealer on the card at age 43)
 

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I would replace your number 2 moment with him winning his first WWE World Title. That is an image that is still shown in montages.
 

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Even though I don't like Shawn Michaels (I'm a huge Bret fan), I can't deny how legendary his accomplishments are. Here are the 10 most significant matches/moments of his career that I remember.

1. Marty Janetty barbershop incident
2. Beating Bulldog for first single title (he was being held back until this)
3. Razor Ramon ladder match Wrestlemania X (showed his talents were rare)
4. Winning 1995 Royal Rumble (moved from midcarder to main eventer)
5. Undertaker Hell In a Cell match (simply a fantastic performance; one of the first major moments in the Attitude era)
6. Montreal Screw Job (cast a shadow over his accomplishments, unfairly somewhat)
7. Dropping title to Steve Austin (did the right thing for business, and was the last time we'd see the young Shawn)
8. Winning WHC at Survivor Series 2002 (the moment you never thought you'd see)
9. Ending Ric Flair's WWE career (respect by and for other greats)
10. Undertaker WM25 match (showed he was still the biggest show-stealer on the card at age 43)
I'd put his Ladder match with Bret for the IC title in there. Granted it was only a house show match but it's better than the one at WM10 and argueably more significant to his career than actually winning his first title against Davey Boy.

Also, if you feel the WM25 match belongs there due to his age, shouldn't you have the WM26 match since he was a year older and just as good?
 

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you should add his 1997 heel turn and DX formation
For me the heel turn and the formation on D-Generation X ranks alongside him beating The British Bulldog for the Intercontinental title which saw him go from ex tag team wrestler to legitimate singles star and winning The Royal Rumble in 1995 which saw him go from mid card star to believable main event wrestler because up until D-Generation X Shawn Michaels was never really a HUGE star but he was the biggest he had ever been from mid 1997.

I am a HUGE Shawn Michaels mark and believe him to be the greatest all round in ring performer that has ever graced a ring but the only mark against him was always his star power quality and name value as he was never a Hulk Hogan, Stone Cold Steve Austin or Rock and despite being the biggest star in WWE in 1996 he became a much bigger star once he turned heel because of how big D-Generation X became.

So many people credit Stone Cold Steve Austin with being the man who started "The Attitude Era" and as the undoubted star of that generation and whilst i will not argue with him being the main man in that era it was Shawn Michaels who ushered that era in and it was Shawn Michaels and Stone Cold Steve Austin who were the men that Vince McMahon wanted to build the whole company around as they were tailor made for that era. A lot of people forget that Stone Cold Steve Austin was out injured in between SummerSlam and Survivor Series in 1997 and Shawn Michaels was the main focus as the new product was starting and even after Stone Cold Steve Austin had come back he was still a mid carder until The Royal Rumble in 1998 at which point WWF was well on it's way with the new product.

He may never have been as big of a draw as The Rock or Stone Cold Steve Austin in that era but Shawn Michaels as the top heel and Stone Cold Steve Austin as the top face short term and long term is what Vince McMahon wanted and as the leader of D-Generation X who were another short term and long term plan that Vince McMahon wanted would have been a very big star and much bigger on a draw than he ever was because people legitimately wanted to tune in to Raw and watch what Shawn Michaels was doing with D-Generation X and what Stone Cold Steve Austin was doing also.

I don't think that Shawn Michaels was ever as big of a draw as he was when he was a heel in 1997-1998 as the leader of D-Generation X which makes me see the heel turn the night after SummerSlam in 1997 as one of the most significant moments in not only Shawn Michaels career but also WWE history because that was more or less the origins of "The Attitude Era" and also the start of D-Generation X was only a few weeks away afterwards.
 

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For me the heel turn and the formation on D-Generation X ranks alongside him beating The British Bulldog for the Intercontinental title which saw him go from ex tag team wrestler to legitimate singles star and winning The Royal Rumble in 1995 which saw him go from mid card star to believable main event wrestler because up until D-Generation X Shawn Michaels was never really a HUGE star but he was the biggest he had ever been from mid 1997.

I am a HUGE Shawn Michaels mark and believe him to be the greatest all round in ring performer that has ever graced a ring but the only mark against him was always his star power quality and name value as he was never a Hulk Hogan, Stone Cold Steve Austin or Rock and despite being the biggest star in WWE in 1996 he became a much bigger star once he turned heel because of how big D-Generation X became.

So many people credit Stone Cold Steve Austin with being the man who started "The Attitude Era" and as the undoubted star of that generation and whilst i will not argue with him being the main man in that era it was Shawn Michaels who ushered that era in and it was Shawn Michaels and Stone Cold Steve Austin who were the men that Vince McMahon wanted to build the whole company around as they were tailor made for that era. A lot of people forget that Stone Cold Steve Austin was out injured in between SummerSlam and Survivor Series in 1997 and Shawn Michaels was the main focus as the new product was starting and even after Stone Cold Steve Austin had come back he was still a mid carder until The Royal Rumble in 1998 at which point WWF was well on it's way with the new product.

He may never have been as big of a draw as The Rock or Stone Cold Steve Austin in that era but Shawn Michaels as the top heel and Stone Cold Steve Austin as the top face short term and long term is what Vince McMahon wanted and as the leader of D-Generation X who were another short term and long term plan that Vince McMahon wanted would have been a very big star and much bigger on a draw than he ever was because people legitimately wanted to tune in to Raw and watch what Shawn Michaels was doing with D-Generation X and what Stone Cold Steve Austin was doing also.

I don't think that Shawn Michaels was ever as big of a draw as he was when he was a heel in 1997-1998 as the leader of D-Generation X which makes me see the heel turn the night after SummerSlam in 1997 as one of the most significant moments in not only Shawn Michaels career but also WWE history because that was more or less the origins of "The Attitude Era" and also the start of D-Generation X was only a few weeks away afterwards.

Nice post. I agree with you. D-Generation X was what ushered in the Attitude Era. I remember watching as a kid and thinking that DX was the coolest thing I had ever seen on wrestling. You didn't know wtf they were going to do each Monday night. You have to wonder what would have happened if Shawn hadn't got injured and left. Would he have became as big a star as Austin and Rock? I guess we'll never know.
 

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For me the heel turn and the formation on D-Generation X ranks alongside him beating The British Bulldog for the Intercontinental title which saw him go from ex tag team wrestler to legitimate singles star and winning The Royal Rumble in 1995 which saw him go from mid card star to believable main event wrestler because up until D-Generation X Shawn Michaels was never really a HUGE star but he was the biggest he had ever been from mid 1997.

I am a HUGE Shawn Michaels mark and believe him to be the greatest all round in ring performer that has ever graced a ring but the only mark against him was always his star power quality and name value as he was never a Hulk Hogan, Stone Cold Steve Austin or Rock and despite being the biggest star in WWE in 1996 he became a much bigger star once he turned heel because of how big D-Generation X became.

So many people credit Stone Cold Steve Austin with being the man who started "The Attitude Era" and as the undoubted star of that generation and whilst i will not argue with him being the main man in that era it was Shawn Michaels who ushered that era in and it was Shawn Michaels and Stone Cold Steve Austin who were the men that Vince McMahon wanted to build the whole company around as they were tailor made for that era. A lot of people forget that Stone Cold Steve Austin was out injured in between SummerSlam and Survivor Series in 1997 and Shawn Michaels was the main focus as the new product was starting and even after Stone Cold Steve Austin had come back he was still a mid carder until The Royal Rumble in 1998 at which point WWF was well on it's way with the new product.

He may never have been as big of a draw as The Rock or Stone Cold Steve Austin in that era but Shawn Michaels as the top heel and Stone Cold Steve Austin as the top face short term and long term is what Vince McMahon wanted and as the leader of D-Generation X who were another short term and long term plan that Vince McMahon wanted would have been a very big star and much bigger on a draw than he ever was because people legitimately wanted to tune in to Raw and watch what Shawn Michaels was doing with D-Generation X and what Stone Cold Steve Austin was doing also.

I don't think that Shawn Michaels was ever as big of a draw as he was when he was a heel in 1997-1998 as the leader of D-Generation X which makes me see the heel turn the night after SummerSlam in 1997 as one of the most significant moments in not only Shawn Michaels career but also WWE history because that was more or less the origins of "The Attitude Era" and also the start of D-Generation X was only a few weeks away afterwards.

i couldn't agree more. as cliche` as his little phrase "i was attitude before it became a catch-phrase" is, it's completely true. in some ways, i think he gets too much credit for things, and in other ways i don't think he gets enough credit. if he hadn't gotten hurt, he may have been bigger...but also i don't think he would of lasted much longer...

and honestly, as corny as this sounds, i think the most significant moment is when he "found Christ" and pretty much saved his life. sure, he would have still been remembered as one of the all time greats, but now is regarded by many as the greatest, if not the top 2 or 3.
 
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