The underrated rivalry between Shawn Michaels and Sycho Sid was one of the bigger main event angles for WWE in the New Generation Era. Michaels was in the conversation with Bret Hart for the best overall performer at the time. Sid received a huge push as the latest big man project that Vince McMahon wanted in the main event picture.Both wrestlers benefited from their time working together as former partners turned enemies. WWE didn’t find the same level of long-term success as Michaels vs Hart or Undertaker vs Mankind. However, they deserve more attention for their noteworthy work together in important scenarios. The following tidbits between Michaels and Sid will show a deeper side to their rivalry.
8 Sid Was Needed To Turn Michaels' Face
The replacement of Diesel as Shawn Michaels’ bodyguard saw Sid taking that role to find success. Michaels losing his WrestleMania 11 WWE Championship match to Diesel saw Sid and Michaels no longer getting along.
Sid brutally attacked Michaels the following night to kickstart the face turn for the Heartbreak Kid. Michaels played a heel for so long that some sympathy was needed towards him. The beatdown from Sid helped Michaels turn face and set up his end game of eventually becoming the face of WWE.
7 WWE Ignored Their Previous Drama When Sid Returned
The early 1995 attack from Sid towards Shawn Michaels set him up for a couple of WWE Championship matches against Diesel and a place in the Million Dollar Corporation faction. Sid left the company towards the end of the year and returned in mid-1996.
The return of Sid saw WWE ignoring the issues he had with Michaels from his previous stint. Sid returned to replace Ultimate Warrior as the face partner of Michaels and Ahmed Johnson. WWE sacrificed the logic to bring in a big name and avoid issues with Warrior no showing the event.
6 Teamed Up In Wild Random Team Survivor Series Match
WWE tried to deliver a unique form of storytelling with a mixed set of partners on teams at the Survivor Series 1995 event. Sid and Shawn Michaels were forced to team along with Ahmed Johnson and Davey Boy Smith against Razor Ramon, Dean Douglas, Owen Hart and Yokozuna.
The wild card atmosphere saw Michaels and Sid failing to get along due to their past drama. Michaels hitting his own partner Sid with a superkick caused him to get eliminated. Sid followed it up by hitting the powerbomb on Michaels before he was removed from the ring.
5 WWE Championship Feud Started Off Face Vs Face
WWE picked Sycho Sid to become the next challenger to Shawn Michaels heading into Survivor Series 1996 in Madison Square Garden. Sid was playing a face character when he won the #1 contender’s spot to challenge Michaels for the top prize.
The heel turn came during the feud when Sid started showing tendencies to cheat or exploit the system. However, Michaels and Sid went into their first title match both as fan favorites, which did Michaels no favors with the audience.
4 Michaels Getting Win Back Was Meant To Be Bigger Moment
The title change at Survivor Series 1996 with Sycho Sid’s first WWE Championship victory was meant to set up a bigger moment. Royal Rumble 1997 taking place in Shawn Michaels’ home stage of Texas saw WWE booking the rematch for greater importance there.
Sid losing to Michaels was the main event over the typical Rumble match that closed the show. WWE had a solid night, but fans still talk about the other event when Sid won the title more. Michaels was losing momentum as a face in the top spot during this time.
3 One Of WWE's First Contract Signing Segments
WWE had a unique contract signing segment between Sycho Sid and Shawn Michaels in the weeks leading up to their Survivor Series 1996 match. Both men were given podiums to answer questions from Jim Ross with the contract signing term used to advertise the segment.
The action did not get physical like most future contract signings, but it showed the tension rising between the two faces. Sid even verbally mocked JR for asking him questions he didn’t agree with the tone of, to drop hints at his later heel turn.
2 Michaels "Losing His Smile" Gifted Sid Another Title Reign
The end of the feud between Shawn Michaels and Sycho Sid was supposed to lead to Michaels defending the WWE Championship against Bret Hart. WWE expected a rematch between the two technical wrestling masters in the main event of WrestleMania 13.
Michaels however opted to retire shortly after winning the title back from Sid with the claims that he “lost his smile.” WWE didn’t plan to put the belt back on Sid, but he received another WWE Championship reign when the company needed a heel to put over The Undertaker as the new plan.
1 First Instance Of Fans Turning On Top Face
WWE fans have become unpredictable over the past few decades when it comes to rebelling against face characters with negative chants. Shawn Michaels was the first major top star to witness that during his WWE Championship reign in 1996.
There were some jeers for a title defense against Mick Foley in Philadelphia, but it reached new heights at Survivor Series 1996. The New York audience booed Michaels out of the building and was in favor of Sid. Not even the heel ending of Sid attacking Michaels’ elderly manager Jose Lothario could change the momentum of the audience rooting for the title change.