Invasion Draft

Ric Flair vs Shawn Michaels in 1996: the classic that came twelve years late

By the Invasion Draft team · Updated 28 October 2026

This article mixes documented history with our own opinion. Anything about matches that never happened, or how they would have gone, is opinion, not fact.

When Ric Flair and Shawn Michaels finally wrestled on the biggest stage, it was WrestleMania XXIV on 30 March 2008, at the Citrus Bowl in Orlando. Flair's career was on the line, and Michaels won with Sweet Chin Music after saying "I'm sorry, I love you" before the final kick. The match is remembered as one of the most emotional in WrestleMania history. But fans who watched both men in 1996 have always wondered how it would have looked twelve years earlier, when Michaels was the WWF Champion and Flair was still one of WCW's top stars.

Shawn Michaels in 1996

Shawn Michaels started 1996 by winning his second Royal Rumble in a row. At WrestleMania XII on 31 March 1996 in Anaheim, he beat Bret Hart in a 60-minute Iron Man match that went into overtime, winning his first WWF Championship. He held it for much of the year, defending against Diesel, the British Bulldog, Mankind and Vader, before losing it to Sid at Survivor Series in November and winning it back at the 1997 Royal Rumble in San Antonio. In 1996 Michaels was arguably the best in-ring performer in the world, fast, athletic and theatrical. The WWF was losing the ratings war, but not because of his matches.

Ric Flair in 1996

Ric Flair turned 47 in February 1996, and he was still a world champion. He beat Randy Savage for the WCW Championship at SuperBrawl VI in February 1996, and rebuilt the Four Horsemen with Arn Anderson, Chris Benoit and Steve McMichael. When the nWo arrived that summer, the Horsemen were one of the groups standing against it. Flair had wrestled for the WWF in 1991 and 1992, winning the 1992 Royal Rumble and the WWF Championship, and had long since proved his style could work in either company.

Why it didn't happen

In 1996 the two companies were at war. Michaels was the WWF's champion and Flair was a WCW star under contract, and neither company would lend talent to the other. Flair returned to the WWF only in late 2001, as on-screen co-owner after the Invasion, and by then Michaels had been retired for nearly four years with a back injury from the 1998 Royal Rumble. Michaels did not return to full-time wrestling until 2002, and by the time they were both active in WWE, it took the setting of a retirement match to make it feel special.

What a 1996 match would have looked like

This section is our opinion. Both men were among the best in history at the same thing: making a crowd believe the match could end at any moment. Flair's style was built on chops, figure-four leglocks, flops and bumping for his opponent, then cheating to win. Michaels was the same template with more speed and athleticism. Flair was one of the influences on Michaels's own style, and you can see it in the way Michaels bumped and sold.

A 1996 match would almost certainly have been long, probably 30 minutes or more, with Michaels as the fiery babyface and Flair as the heel veteran trying to steal it. Flair working the leg to set up the figure-four, Michaels fighting back with flying elbows and the kip-up, the crowd waiting for Sweet Chin Music. It's easy to picture because both men had done versions of it against other people.

Who wins?

Opinion. In 1996 Michaels was the younger star on the rise, and if it had been on a WWF card, he wins clean with Sweet Chin Music. On a WCW card, Flair wins with his feet on the ropes or a Horseman distraction, and the WWF's champion gets to look like he was robbed. Either way, the match would have been a strong candidate for match of the year, and the rematch would have been even better.

Why 2008 still worked

It's tempting to say the 2008 match was a consolation prize. We don't think so. The emotion of WrestleMania XXIV came from twelve extra years of history and the knowledge that it was the end. A 1996 version would have been a better athletic contest and the 2008 version was a better story. Both are worth having, and only one of them happened.

Try it in the game

In Invasion Draft, a WWF 1996 face spin may offer Shawn Michaels, and a WCW 1996 heel or face spin may offer Ric Flair, depending on the timing of his turns. Put either one in your World Champion slot and you will probably score well, but you can only see them meet if the reel and your opponent's card both cooperate. Tag them with a strong manager, such as a Horseman for Flair, and you'll get a boost to the match.

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