10 Best Heel Turns Of The WWE Attitude Era

8. Undertaker (1998)

Triple H Stephanie McMahon
WWE

Mark Calaway pipebombed in 1998, and it's appropriate to refer to The Undertaker by his real name in this instance because for that one night, in expressing his discontent for the company values, he was absolved of the Dead Man gimmick, and this was two years before his American Badass stint.

Ultimately, this was only a precursor to one of the most sinister segments of 'Taker's wrestling career. A few months on from this, The Undertaker went full heel by realigning himself with Paul Bearer at Judgement Day. So began the Ministry of Darkness, a new stable with some fresh talent and a lot of weird sacrifice stuff.

During his first night of new-found heeldom, a rejuvenated and decidedly nasty Undertaker explained that there had been a reconciliation, and that the Ministry would unleash 'a plague for which the world has never seen'. With the Attitude Era in full swing, The Undertaker was able to prove he was capable of stepping up to the edgy content table, and effortlessly so.

All things considered, it was one of his coolest ever promos.

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