When was the best time for Undertaker to retire?

[Hoodoo Child]

The way the Brock feud painted Taker as a sore loser had me . He sat at home for over a YEAR then finally said "fukk it. I'mma go get this nikka". They backfired hard trying to make Brock the ultimate heel post WM30. Taker was the one getting boos when he returned.

 

[motionlessZombie]

2012

 

[FS4LFE]

2014 when the streak ended.

 

[MrFirst2doit]

The streak needed to be ended, that's wrestling.... You have your time then pass the torch onto someone else... I would of ended it with a redemption win against Sting instead of sting jobbing to triple H

 

[TheGreatShowtime]

Should've retired whenever HBK retired. But realistically, he should've retired in 2000 and saved us from having to watch MAGA ABA Taker

 

[HipHopStan]

2012 would've been the ideal time to go after his Mania storyline with HBK/HHH ended, however we wouldn't have got his fantastic Mania 29 against Punk.
2014 would've been another good time after the streak ended, but we were cutting it close to his 25th anniversary in the company.
2015 would be my answer. He was nowhere near his prime anymore, but he put on two fun, entertaining matches with Brock and we got to see the B.O.D. tag team one last time for his 25th anniversary.

He was shot beyond that point although his tag match with Roman against Drew and Shane was fun as was his Graveyard Match with AJ at the 2020 WrestleMania, He had workers that could help him out, sell, and not make him put in as much work.

 

[SirMo]

It is the year 1992, Undertaker has just defeated Kamala at Survivor Series. He then gets in the ring, strips naked and starts masturbating until he ejaculates, right onto the canvas. He then squats over his hat, takes a big shyt into it, and throws it into the crowd - shyt flies everywhere - all over peoples faces. He then walks to the back naked, semi erect. This would literally be the most memorable thing ever.

 

[Broad Street Bully]

It is the year 1992, Undertaker has just defeated Kamala at Survivor Series. He then gets in the ring, strips naked and starts masturbating until he ejaculates, right onto the canvas. He then squats over his hat, takes a big shyt into it, and throws it into the crowd - shyt flies everywhere - all over peoples faces. He then walks to the back naked, semi erect. This would literally be the most memorable thing ever.

https://media.tenor.com/txO2AWE0L5UAAAAM/what-the-fukk-was-that-what-the-fukk.gif

 

[Metal Face]

2012 to end his career on a high

 

[drifter]

Right before he got left standing outside the Cavs locker room like a thot

 

[Wolfpac]

It is the year 1992, Undertaker has just defeated Kamala at Survivor Series. He then gets in the ring, strips naked and starts masturbating until he ejaculates, right onto the canvas. He then squats over his hat, takes a big shyt into it, and throws it into the crowd - shyt flies everywhere - all over peoples faces. He then walks to the back naked, semi erect. This would literally be the most memorable thing ever.

2012. Would've made "End of an Era" mean something. Instead, just like "Once In A Lifetime", it ended up not meaning shyt lol.

 

[Broad Street Bully]

Right before he got left standing outside the Cavs locker room like a thot

In full costume had to be wild humiliating

 

[Notorious 1 E.Y.E.]

When brock beat him cause he was absolutely cooked
Was his last match here he could accrual do the whole match the one with punk?

That match with roman was one of the worst matches ive ever seen and he put roman in an awful position

 

[nairdas]

2012 for sure. That was a great story and a great match. Perfect to retire on.

 

[James Dean]

Lot of logical choices really.

2012 end of an era for sure would work.

The streak ending is good as well but I really enjoyed the content he and Brock did after that. Especially the cowardly elements they were adding unto taker with those low blow wins. The crowd was even split on taker too.

If not those two he should have hung it up after Roman. there were a lot of stinkers after that and like a handful of passable moments ( Cena 2018, aj boneyard etc)