Tear Jerker / WrestleMania

• The end of the WrestleMania VII retirement match between Ultimate Warrior and Randy Savage. Savage was being berated by Sensational Sherri, when she was attacked by a returning Miss Elizabeth. A stunned Savage just stood there, confused while a tearful Elizabeth explained why she was there...she still loved him. They slowly walked towards each other and embraced. Half the LA Memorial Sports Arena burst into tears over the raw emotion of the event. It set up a great summer storyline culminating in their (kayfabe) wedding at that year's SummerSlam.
• Roddy Piper and Bret Hart's match at WrestleMania VIII. After a grueling match where the younger Bret managed to consistently overpower Roddy, even after the Rowdy One started fighting dirty, Roddy launches Bret into the ref and knocks the official out. Knowing that anything he does before the ref recovers won't get him disqualified, Roddy goes for the ring bell and is about to bludgeon Bret with it... when he's bombarded with a cascade of boos from the crowd. Roddy looks around, almost disbelieving at the people who up until that point had been his fans until he crossed the line. The tears turn happy when Roddy takes a moment and then throws the bell away to finish the match right win or lose.
• Shawn Michaels winning the WWF Championship at WrestleMania XII after an Iron Man Match with Bret Hart, fulfilling the "boyhood dream".
  Vince McMahon: The boyhood dream has come true for Shawn Michaels!
• Chris Benoit winning the World Heavyweight Championship at WrestleMania XX, and his celebration with then-WWE Champion Eddie Guerrero. This is a very sad instance of Harsher in Hindsight, since both would be dead within three years, especially given the circumstances behind Benoit's death.
• Ric Flair's retirement match at WrestleMania XXIV. At the end, it became clear to Shawn Michaels he was facing a Shoot the Dog situation. A crying Flair coaxing Shawn to finish it, knowing it was time. Shawn was so overcome, he couldn't even "tune up the band" for the Sweet Chin Music. Instead, he only says "I'm sorry. I love you." and hit his Sweet Chin Music to finish the match. After the pin, Shawn hugged Ric Flair, and was in tears all the way up the ramp. And given they were at the Citrus Bowl in Orlando, that was a looooooong ramp.
• The ending to the match between Shawn Michaels and The Undertaker at WrestleMania XXVI. Despite going out defiant, it's sobering to know that Michaels desperately staked his illustrious, decades-long career on this match and still couldn't win. Seeing the fireworks and pyrotechnics going off feels oddly-dissonant, knowing that one of WWE's longest-tenured stars' career ended then and there. One last handshake and hug later, and Michaels can only go over and start saying his goodbyes to the crowd. This line from Michael Cole drives it home:
  Cole: Shawn Michaels' career... is over.
• At WrestleMania XXX, The Undertaker's Streak is broken by Brock Lesnar. As Lesnar and Paul Heyman leave the ring celebrating, Taker and by extension the entire crowd are just left stunned by what had transpired as if they still can't believe it happened. After the reality finally sinks in, Taker just...leaves the ring, acknowledging his defeat as the crowd chants "Thank you Taker!"
• WrestleMania 33: The main event was The Undertaker vs. Roman Reigns. The Undertaker starts off the match really dominant, with Reigns repeatedly pummeled and flung from the ring. Even after tiring, the only offense Reigns really gets is opportunistic attacks while Undertaker's guard is down. Yet as the match goes on Undertaker just... falls apart. He struggles to even stand, takes the worst of every bump, ends up unable to even raise his hands to defend himself. But he won't stay down. What we end up with is an increasingly tormented looking Reigns pummeling an old man, looking more like a beatdown than a fight. And however much the crowd wills it, Undertaker never gets a second wind. He just takes finisher after finisher, until finally... he doesn't get back up. The Undertaker loses to Reigns, bringing his record to 23-2. After the match was over, Undertaker took off his gloves, coat and hat, laying them in the ring, appearing to retire. Rather than a huge explosion of fireworks, the show ended with the lights going down, Taker's gong echoing through the arena.
  
  Say what may be said about Reigns, but this picture of him backstage after the match kinda explains how much of a toll ending the Deadman's career has been for him. Moreso his tweet hours later:
  Reigns: I did what I had to at #WrestleMania but it doesn't change the fact Deadman held the yard down for years. For that...#ThankYouTaker #Respect
• At Night Two of WrestleMania 38, Triple H opens the show, nearly 2 weeks after announcing his in-ring retirement, doing one more classic entrance down the ramp, one more legendary pose and leaves his boots in the ring. Thank you, Hunter.
• On Night One of WrestleMania 39, Sami Zayn and Kevin Owens took on The Usos for the Undisputed Tag Team Championship, bringing a grand curtain down upon a long feud between the former two and the Bloodline: half a year for Zayn, including his intensely emotional conflict with Roman Reigns, and almost a full three years for Owens. At the end of the match, Zayn closes the chapter with Jey Uso - the member of the Bloodline with whom Zayn had most strongly bonded before the implosion with Reigns - with a line to make Shawn Michaels proud before delivering a title-winning trio of Helluva Kicks:
  Sami: I'm sorry. You tried, Uce.
  • On Night Two however, Cody Rhodes would not be as lucky as the aforementioned Owens and Zayn. In one of the cruelest examples of Yank the Dog's Chain, Rhodes would ultimately lose against Roman Reigns in the main event after interference from The Usos and Solo Sikoa. It's no secret that winning the WWE title has always been Cody's dream after his father and brother were never able to, and Cody himself has never even competed for it before. To lose on the biggest stage of his career and after his grand comeback at last year's WrestleMania is genuinely heartbreaking to see, especially when his family were at ringside, including his wife and daughter. A picture is worth a thousand words.
• On Night One of WrestleMania XL, Jey is about to finish off Jimmy, who cries in the ring and apologizes for what happened. Jey can't go with the attack and hugs his brother...only to be blindsided by Jimmy taking advantage of his brother's sympathy to attack.
• On Night Two of WrestleMania XL, Drew McIntyre successfully defeated Seth "Freakin" Rollins to win the World Heavyweight Championship and get his moment and tell CM Punk that he's next. Right after Punk assaulted him however, Damien Priest ran in to cash in his Money In The Bank contract and stole his win. McIntyre can only look dejected that his big WrestleMania moment was swept away after celebrating it.
• Also on the above show: Seth Rollins making good on his promise to "be your SHIELD" to Cody Rhodes, coming out in his old combat gear to run the distraction on Roman Reigns. An amazingly emotional moment on its own merits, being the ultimate culmination of Seth's years-long redemption arc following his betrayal of the SHIELD, but what makes it tragic is the payoff: Roman choosing to take vengeance on Seth, smashing a chair into his back in payment for his betrayal all those years ago instead of putting Cody away with the weapon instead, unwittingly giving Cody the opportunity to win and functionally sacrificing his championship reign and all of his accomplishments in favor of avenging his Start of Darkness. Seemingly, no matter what good happens to him or what he achieves, Roman's entire career will always, in the end, boil down to that one night in 2014.
  • Along with Heartwarming, but during Cody's celebration, he's tearing up as he hugs his mother, both happy yet also sad that his father wouldn't be here to see him win the championship.