#9 The Rise of the Lord of Darkness
In 1997, the WWE had begun its Attitude Era, and the fan base was somewhat older and more jaded than in ages past. In order to appeal to the new target demographic of males 18-36, the WWE changed a lot of the gimmicks of their long standing wrestlers.
The Undertaker was an icon in the WWE already, and the decision was made not to change his name or appearance overly much. However, the idea of an immortal zombie wrestler didn't seem to fit the Attitude Era mold. The Undertaker was re-cast as more of a cult leader who led a gothic life style rather than an actual supernatural force.
During this period, he turned heel for the first time in years, and gathered his own stable, the Ministry of Darkness. While many fans considered this stable to be on the corny side, with their 'sacrifices' and crucifixions, it did give a lot of forgotten mid card wrestlers a chance to shine, such as Viscera and Farroq and Bradshaw.
Eventually, however, The Undertaker would undergo his most radical transformation yet.