Razor Ramon and Shawn Michaels' most memorable matches were WrestleMania X — when Michaels was stripped of the Intercontinental Championship — and their ladder rematch at SummerSlam 1995. Although being great friends outside of the ring, they were involved in one of the most controversial moments in WWE history, the curtain call.

Bret Hart and Michaels are perhaps best known for their controversial match at Survivor Series 1997, when Vince McMahon ordered the bell to ring, screwing Hart out of the championship before he left the WWF for WCW. Michaels feigned innocence but later admitted he was in on it, ending a feud that was real both on and off the screen.

Like Razor Ramon, Diesel and Michaels were significant opponents in the ring, but the best of friends outside of it, making a natural dynamic between them. Michaels was responsible for Diesel joining the WWF, and they even captured the tag titles together before eventually heading in separate directions until returning together to feud as opponents.

As a longtime WWE executive and former stablemate in the legendary faction D-Generation X, Triple H was another personal friend of Michaels. After Michaels returned from a back injury, Triple H was the top guy in the industry and the perfect opponent for him at SummerSlam 2002, leading to numerous rematches.

Chris Jericho was a signature opponent for Michaels, and the beginning of their feud together was rooted in that student-teacher concept. First squaring off at WrestleMania XIX, their rivalry included low blows and Jericho punching Michaels' wife in the face at SummerSlam, culminating in a bloody ladder match at the No Mercy 2008 pay-per-view.