In this episode of With This Ring, Ryan and Cindy look at the Heartbreak Kid Shawn Michaels (Part One). In this episode they look at the first phase of Shawn Michaels WWF career, from early days as a Rocker to degenerate World Champ blowing out his back in a casket match. They talk about the Rockers and how they evolved, a fateful trip to a barbershop and two early classic Raw matches. They also attempt to answer the question is he a sexy boy? All this and much more on this edition of With This Ring!
- Rockers vs. Brain Busters - Madison Square Garden, January 23, 1989 (Heartbreak & Triumph)
- Rockers vs. Hart Foundation- Madison Square Garden, November 25, 1989 (My Journey)
- Rockers vs. Orient Express - Royal Rumble 1991
- Shawn Michaels vs. Randy Savage - World Title Match, UK Rampage 92
- Shawn Michaels vs. Bret Hart - Ladder Match, July 21, 1992 (Smack 'Em Whack 'Em)
- Shawn Michaels vs. Marty Jannetty- Intercontinental Title Match, Raw July 19, 1993
- Shawn Michaels vs. Razor Ramon - Raw August 1, 1994
- Shawn Michaels vs. Diesel- WWF World Title Match, Good Friends, Better Enemies
- Shawn Michaels vs. British Bulldog- WWF World Title Match, King of the Ring 1996
- Shawn Michaels vs. Undertaker - WWF World Title Casket Match, Royal Rumble 1998
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