When did The Undertaker retire from WWE?

The Undertaker is considered to be among the greatest professional wrestlers of all time and the greatest character in WWE history. While "The Undertaker" character was created by Vince McMahon, he needed the perfect fit for the role.

After an unprecedented three-decade-long career, The Undertaker retired from WWE in Survivor Series 2020 - exactly 30 years after his debut. He revealed several months earlier in 'The Last Ride' documentary that he was done with his WWE career.

"My time has come to let The @undertaker rest ... in ... peace." #SurvivorSeries #FarewellTaker #Undertaker30 pic.twitter.com/Mg9xr8GB94

— WWE (@WWE) November 23, 2020

Mark Calaway was in a tricky position in his wrestling career in the late 1980s. He was told by WCW that nobody would pay big money to see him. Describing it as a moment where the chip on his shoulder grew in size, The Undertaker sought out a chance to sign with WWE (then known as WWF) through his connections with Bruce Prichard and Paul Heyman.

Famously, Vince McMahon wasn't interested in signing Mark Calaway at first. When he finally relented to Bruce Prichard's pleas, Vince McMahon met with Callaway and told him that there was nothing for him.

This picture will go down in the history books. This is a legacy. This is respect. This is honor. This is loyalty. This is love. This is passion. This is the Phenom. This is the Deadman. This is The Undertaker. #ThankYouTaker #Undertaker30 #SurvivorSeries pic.twitter.com/Fi2ODWEDB0

— The Angle Podcast (@theangleradio) November 23, 2020

In late 1990, Calaway finally signed with WWE and became The Undertaker - debuting in Survivor Series 1990. It would mark the start of a historic run in WWE where The Undertaker would outlast multiple generations of superstars.

The Undertaker's first retirement and reception by fans

WrestleMania 30 in 2014 was when The Undertaker's historic WrestleMania undefeated streak came to an end at 21-1. Brock Lesnar was the man to end the streak in a match where The Undertaker looked far past his prime physically. He even suffered a concussion in the match and admitted to remembering nothing after a point.

Vince McMahon even left WrestleMania to go with The Undertaker to the hospital. While many fans felt it should have marked the end of The Undertaker's career - it didn't.

He would return each year for an appearance or more in the ring. As each year passed, it became painful for fans to watch The Undertaker slow down in the ring and force himself into a situation that he didn't need to be in.

WrestleMania 33 in 2017 marked The Undertaker's first retirement. In a non-title main event against Roman Reigns, The Undertaker lost at WrestleMania for the second time and put his gloves, jacket and hat in the center of the ring, signaling the end of his career.

He even broke character and kissed his wife Michelle McCool, who was ringside to watch his retirement. WWE went to the extent of bringing back Jim Ross to call the main event of WrestleMania.

It was another difficult match to watch, as The Undertaker had to be carried by the younger and more agile Roman Reigns. Despite the retirement, he would come back a year later at WrestleMania 34 to defeat John Cena in less than three minutes.

The Undertaker's final match was at WrestleMania 36. It was a pre-taped cinematic bout called the 'Boneyard Match', and The Phenom returned as his old biker character one last time to defeat AJ Styles.

It was arguably the most well-received match of WrestleMania 36. It was also the perfect farewell for The Undertaker before he officially called it quits 7 months later.