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The Rock and The Undertaker are easily two of the biggest icons in the history of the wrestling business. Yet they went on to have very different careers.
The Rock's wrestling career was very short compared to the other greats. After stumbling out of the blocks, he got over quickly and remained a main event player for the rest of his career before going to Hollywood and the becoming one of the biggest actors in the world, if not the very biggest. His time as a full-time wrestler was very short. He debuted in 1996 and had pretty much become a part-timer by 2002 and would leave for good in 2003. Since then, he has made sporadic appearances from time to time and even had a short run in 2013, when he even won the WWE Championship.
In contrast, The Undertaker had one of the lengthiest careers at the top that the wrestling industry has ever seen. After failing in other companies with different gimmicks, he would debut in the WWE in 1990 and strike gold. It was lightning in a bottle, and he would go on to be a top of the card performer for the next three decades, and many consider The Undertaker the greatest in the history of the company.
For all of their talent, name value, and ability though, The Rock and The Undertaker never ended up having a great feud with each other.
The Rock And The Undertaker Would Cross Paths On Several Occasions
It was not like The Rock and The Undertaker had not crossed paths often enough during their time in the WWE. Their first feud was when The Corporation turned on The Rock and joined forces with The Undertaker's Ministry of Darkness.
Later on, they would almost strangely face over The Undertaker's elimination at the hands of Maven in the Royal Rumble. Later that same year, they would fight once again, this time over the WWE Championship, with The Rock coming out on top against The Deadman in a triple threat match that also involved Kurt Angle.
Overall, the two did not face each other one on one too often but also had enough encounters to have had a memorable feud which they did not.
The Two Just Did Not Mesh Well Together
Sometimes, no matter how great the two individuals involved in a feud are, they just do not mesh well together and that was also the case with The Rock and The Undertaker.
Their gimmicks did not seem to be compatible enough to create a compelling storyline and in the ring, none of the men did their best work against each other. The Rock was never known for his ability in terms of a world-class in-ring worker. On the other hand, The Undertaker would go on to have a number of great matches, but they were mostly later on in his career.
Thus, while it might have involved two of the most iconic characters that the business has ever seen, it just was not the right fit.
The Attitude Era Was A Period Of Pure Chaos
There was no other era in wrestling like the Attitude Era. WCW had raised the bar with the NWO angle in 1996 but soon enough, the WWE not only reached that level but surpassed it.
One of the biggest reasons for that was the incredible talent that the WWE had at the top of the card at the same time. It can be argued that that was the deepest roster of legitimate main event-level talent that has ever been assembled. Stone Cold Steve Austin, The Rock, The Undertaker, Mankind, Triple H, Kurt Angle, Kane, and many more were at the top of their games at the same time, which led to a wealth of options in the WWE Championship picture.
Thus, the action moved very quickly with multi-man matches at the top of the card taking place regularly and the title changing hands on a regular basis.
Thus, very little was given time to breathe and this was another reason why The Rock and The Undertaker never got the chance to have a proper feud.
Neither The Rock Nor The Undertaker Suffered Because Of It
The Rock and The Undertaker might have never engaged with each other in a memorable feud, but neither of their careers suffered because of it.
The Rock had a short in-ring career but would have epic feuds with the likes of Stone Cold, John Cena, Triple H, Mankind, and many other top stars.
On the other hand, The Undertaker was involved in great feuds with the likes of Kane, Shawn Michaels, Mankind, Brock Lesnar, Edge, Batista, Randy Orton, and several others through the course of his three-decade-long career.