The Undertaker

Top 10 What If Scenarios Involving The Undertaker

The Undertaker had a phenomenal career spanning decades, but missed opportunities have left fans wondering, what if?

The Undertaker is one of the most famous wrestlers to ever step foot in a wrestling ring. Even though he rose to prominence during the Attitude Era, Undertaker had been wrestling in the WWE since 1991 before Raw was even a television program. He was a stalwart for the company through thick and thin.

With a career that spanned multiple decades, it’s hard to argue that the Undertaker didn’t have one of the greatest wrestling careers of all time. Still, there are a ton of “what if” situations, storylines, and moments regarding the Undertaker that many fans still wonder about even years after his retirement.

10/10What If He Became A Star In WCW?

Mean Mark Callous

The Undertaker made such a big impact in the WWE that some fans forget he was a member of WCW as “Mark Callous” and “Mean Mark.” His time with the company was mostly forgettable, and he was even at one point told that “nobody would ever pay to see him wrestle.” Some fans wonder what would have happened if things had worked out for ‘Taker at WCW.

It seems like a stretch to assume he would have adopted the Deadman gimmick. Still, he was a great company man and would have likely contributed to WCW, especially after the arrival of Kevin Nash and Scott Hall.

9/10What If “The Streak” Never Ended?

Undertaker WrestleMania 30 Cropped

Easily the biggest “what if” moment of The Undertaker’s career relates to his famous WrestleMania streak. Most WWE fans agree that The Undertaker’s streak should have lasted his entire career. As we all know now, Brock Lesnar broke the streak at WrestleMania 30, and (for some reason) Roman Reigns also beat him at WrestleMania 33.

With two losses at ‘Mania, a large part of the magic associated with Taker’s WrestleMania relationship was largely erased and if the streak had never ended, the Undertaker’s career would be as associated with WrestleMania as best big-time entrances are. The Undertaker’s streak now feels like a moment in time rather than a legacy he left.

8/10What If Undertaker Wrestled Shawn Michaels In A Regular Singles Match At The 1998 Royal Rumble?

Shawn Michaels v The Undertaker Royal Rumble 1998 Cropped

Despite suffering a ton of injuries over his career, the herniated disk that Shawn Michaels suffered in a Casket Match at the 1998 Royal Rumble changed the course of wrestling. Sure, he would have inevitably handed off the baton to “Stone Cold” Steve Austin but just imagine an Attitude Era where The Rock, Austin, Shawn Michaels, and The Undertaker, were all active wrestlers.

Many fans don’t even realize that the injury that Michaels suffered by hitting the casket against The Undertaker forced him to miss almost all of the Attitude Era. If the Undertaker and Michaels had wrestled a regular singles match, HBK would have likely never been injured, changing the course of the WWE in a big way.

7/10What If Kane Never Joined Undertaker’s Backstory?

Kane WWF Debut With Undertaker

Although Kane became a top wrestler thanks to his size and presence, many fans forget that he reignited The Undertaker’s career when he debuted at Badd Blood: In Your House in 1997. The Undertaker was one of the top names of the company feuding with Shawn Michaels, but his entire presence had begun to grow a bit stale.

If it not for the introduction of Kane and the awesome backstory that added layers to the Deadman, there’s no telling how long the Undertaker could have continued on top. The introduction of Kane also brought a darker side to The Undertaker that would lead to some of his more memorable moments, like the Ministry of Darkness.

6/10What If Undertaker Wrestled The Fiend?

Undertaker & Fiend

Even in his later years, The Undertaker was always able to elevate a great storyline. The potential between him and Bray Wyatt’s The Fiend is massive because they are two of the most inventive gimmicks in the history of the WWE. Some fans will often wonder what a feud between the two of them would look like.

There’s no doubt it would be a main event attraction. By the time The Fiend arrived on WWE television, the Undertaker was already out of the door. Even Undertaker himself wishes he had wrestled the Fiend.

5/10What If Undertaker Had A Better Feud With DDP?

Sara DDP Undertaker

DDP had so much success at the tail end of WCW that he could have been a great addition to the WWE roster after the company purchased WCW in 2001. There was such a lack of star power after WCW left the air that the Invasion angle ended up being subpar.

DDP also had one of the worst introductions to the WWE of any WCW star. He was presented as a stalker in a forgettable storyline with the Undertaker and DDP’s career never recovered. If he would’ve had a true feud with Undertaker, DDP could have been a massive former WCW star on WWE television.

4/10What If Jeff Hardy Beat Undertaker For The Undisputed Championship?

Taker v Jeff

The match that helped launch Jeff Hardy’s career as a solo wrestler happened against The Undertaker on an episode of Raw. Jeff Hardy was well known for innovating the Ladder match meanwhile The Undertaker competed in very few of them over his career.

The two clashed in a Ladder match for the Undisputed WWE Title that ended with a victory for The Undertaker. Jeff Hardy would eventually become world champion in the WWE, but many fans wonder how Jeff’s career would be different if he had beaten Undertaker to win the title earlier in his career. He was already massive and would have been given a chance to be the first unlikely champion of his generation.

3/10What If Undertaker Vs Sting Happened In The WWE?

The Undertaker vs Sting

The dream match that Sting and every WWE fan wanted when the Icon arrived in the WWE in 2014 was a match against The Undertaker. Everyone knows the two would have put on a classic despite their ages because their legacies are tremendous. Instead, the fans got a lackluster run in the WWE from Sting that was mostly forgettable.

If Undertaker versus Sting had happened how would it have impacted the legacies of both superstars, and also how big could it have been? Would it have made Sting’s WWE run memorable? We’ll never know the answer to this question because the match never happened in the WWE.

2/10What If He Never Returned As The Deadman?

Undertaker Deadman WrestleMania 20 Cropped

​​​​The Undertaker’s move from the Deadman to the American Badass was a necessary gimmick change even though fan reactions were very mixed. The American Badass gimmick had its moments, but it never elevated Undertaker beyond his peak as the Deadman.

Some fans wonder what would have happened to Undertaker’s career if he had remained as the American Badass and never brought back his old gimmick at WrestleMania 20. In all honesty, it would have likely led to a quicker end to his WrestleMania streak and a shorter life for his career overall in the WWE.

1/10​​​​​​​What If Undertaker Left WWE During The Monday Night Wars?

The Undertaker with Paul Heyman in WCW

The Undertaker is one of the men responsible for a part of the ratings boost that WWE received during the Monday Night Wars. Undertaker has said that there was a time when he considered moving over to WCW from the WWE.

Ever since ‘Taker spoke that thought into existence, fans have debated how the move could have shifted everything during the Monday Night Wars. WCW was always destined for failure, but Undertaker would have given them something that kept them hot for longer.​​​​​

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