On a 1989 episode of Saturday Night's Main Event, the Blue Blazer said he would (paraphrasing) "jump from the rafters" if he needed to, to defeat Ted DiBiase. The Blue Blazer, of course, was Owen Hart.
One of the paid advertisements that the New World Order ran on WCW Monday Nitro saw Sting's entrance parodied by having someone cut the wire and having an action figure fall into a toy ring. As the video ended, the Sting doll was placed into a casket. The video aired in late 1997 to build towards the Starrcade main event with Sting and Hulk Hogan. However, this uncomfortably mirrored the Owen Hart tragedy that took place about a year and a half later.
A promo for WrestleMania 19 had a voice-over talking about what wrestlers go through to make their mark on history and become immortals, and when it says "Someday, we will die", it focuses on Eddie Guerrero. It's rather uncomfortable to watch these days, because of his death two years later.
During their match at No Way Out 2004, Brock Lesnar tells Eddie to "just die". It is extremely uncomfortable to hear to say the least.
An issue of RAW Magazine with an open letter from "Good Ol' JR" Jim Ross, about WrestleMania 21, tells how proud every wrestler should be of the work they accomplished getting to the event. He also advises all of them to enjoy it because "none of us are guaranteed to make it to WrestleMania 22''." Whether he was talking about employment or not, the words sting knowing that this was Eddie Guerrero's final WrestleMania.
At the first ECW One Night Stand, Mike Awesome does a Suicide Dive onto Masato Tanaka, and Joey Styles said "It's a damn shame he didn't really take his own life!" A few years later, Awesome killed himself.
When Chris Benoit and his family were found dead the morning of a scheduled 3-hour episode of Raw, the show was scrapped and replaced with a special episode dedicated to his past wrestling career. It was found out very soon after the episode aired that he was likely to have murdered his own family, then committed suicide.
What makes this so bad is that the WWE tried to avert this (they aborted a storyline about Vince McMahon "dying" when his limo exploded) but the very attempt itself caused it to be played straight. Talk about a no-win situation...
Every shot to the head and every diving headbutt during Benoit's career is harder to watch since brain damage is thought to have contributed to the murders/suicide.
A few years prior, a Smart Mark website published an "interview with a mark," as a way of helping their readers understand the mindset of a casual fan. The one thing the "mark" said that the Smart Mark interviewer approved of was that Chris Benoit was the one guy in WWE whom he legitimately would not want to meet in a dark alley.
When he was in WCW, Benoit had a feud with Kevin Sullivan over Woman...the future Nancy Benoit. At Clash of the Champions XXXIV in 1997, Dusty Rhodes referred to it as a "domestic dispute". Ouch...
Just like Madden NFL has its Madden Curse, WWE has its Undertaker curse, where, in the SmackDown VS RAW series, the wrestler feuding with the Undertaker ends up dying in real life. It first happened with Eddie Guerrero in SmackDown VS RAW 2006, in which it ends in a Casket Match. Guerrero died 2 days later. It got worse in the following year in a feud with Chris Benoit. The creepiest part? Undertaker says to him, "While your family mourns over your dead carcass, your family will have no one to blame but you." Brrrr.
The in-ring segment where Kharma breaks down in front of the Divas and then announces her pregnancy next week looks even more disturbing now with the news that she actually lost the baby and there was no successful birth.
During the Kane-Matt Hardy "'Til Death Do Us Part" match for Lita at Summerslam 2004, a sign can be seen in the crowd reading "Lita is a Dirty Slut." Less than a year later, the scandal in which Amy "Lita" Dumas cheated on real-life boyfriend Hardy with Adam "Edge" Copeland would break out, resulting in Lita becoming one of the most-hated Divas in the WWE and resulting in her leaving the company in disgrace in November 2006.
Early 2012, the writers started a storyline where Cena kisses Eve Torres, who Cena's "friend" Zack Ryder was in love with. The storyline was quickly aborted with Eve being rejected by Cena but the Rock (who was feuding with Cena) pointed out that Cena was a married man kissing another woman. Several months later, Cena got divorced and former WWE wrestler Ken Dykstra (of the Spirit Squad infamy) revealed that not only was he fired from WWE because Cena stole his fiance but that he then proceeded to fire said fiance several months later. And why? Because Cena was engaged at the time and Dykstra's ex gave him the ultimatum to choice between women.
This one, however, was later debunked by Cena, the company, and Mickie James herself, who maintains the two of them are still friends. Like John Morrison, Mickie James decided to pursue other interests rather than resign, and once she was ready, WWE's womens division was (and still is) underappreciated and underserved, thus she decided to go to TNA. Also, Dykstra has been very vocal and vindictive toward the company, sniping at everyone from the McMahons to Randy Orton to Triple H to even Mickie James herself.
In addition, the Eve angle came after Cena and his wife had filed for divorce which apparently had been coming for some time. The kicker? despite his on-air state, the strife and divorce was reportedly making Cena quite miserable. And the company knew it but went on with it.
On Colt Cabana's Art of Wrestling podcast (and his own documentary), Nigel McGuiness tragically predicts that the current generation of wrestlers will become "zombies" with post-concussion syndrome. Recently, Daffney has been forced out of the ring due to concussions. Her nickname in TNA was "Zombie Hot", and based on recent interviews, it's becoming more of a fitting name per Nigel's definition.
After Jerry Lawler suffered a thankfully non-lethal heart attack, it makes some of his jokes about Jose Lothario a bit hard to listen to, especially the one about Lothorio's heart being clogged with a jalapeno in the aorta. Lothario isn't the only one, either: other subjects of the King's heart attack/heart problem jokes over the years include Brother Love (Pruce Pritchard) and even Lawler himself. Even after recovering from his own heart attack he continues doing it, which may mitigates this somewhat, but bears to wonder how.
In TNA, Taylor Wilde defeated Awesome Kong to win the Knockouts Championship and $25,000 in Kayfabe. Emphasis on the last word. It would later come out that Taylor had been seriously underpaid by TNA and was discovered working a minimum wage job at Sunglass Hut while she was Knockouts Champion.
To twist the knife further, he last appeared on April 7, 2014 (The night after Wrestlemania XXX) talking about how one's spirit can become immortal (Full quote can be found on his page). Ouch.
The Undertaker's entrance at WrestleMania XXX featured caskets with the names of every opponent he's defeated at past Wrestlemanias. The problem is that includes caskets for Giant Gonzales and Big Bossman, who are actually dead.