4. “I’m sorry. I love you.”
Retirement can be an emotional affair, and professional wrestling makes things more interesting by perhaps being the only industry where co-workers can inadvertently force one another to hang up their boots for good. Perhaps the most legendary retirement match in WWE took place at WrestleMania XXIV in 2008, when Shawn Michaels put to rest the career of WWE Hall of Famer Ric Flair. Flair and Michaels have both brought up the waterworks on a few occasions, and this match was probably the most sustained instance of two wrestlers crying to make the list.
The next night on Raw, Flair would receive a bombastic send-off featuring dozens of his old friends from the industry all breaking down in tears, but at WrestleMania, no one seemed more affected than the man taking his career away from him. Michaels was wrestling against his will, while at the same time the being the caliber of showman who couldn’t help but put on an epic encounter and do his best to win, thus causing him pain every time he attacked one of the preeminent idols of the business. Michaels and Flair both had tears streaming down their faces in the final moments of the match, as HBK looked Flair dead in the eyes and told him, “I’m sorry. I love you,” before planting him with a Super Kick that retired The Nature Boy once and for all.
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