Like his baby brother before this, where on earth do we start with The Undertaker? Well, he is the Lord of Darkness and leader of the Ministry of Darkness so who else could we have as number one on a list of the best dark characters in WWE history? 25-years later and Taker is still going strong in the ring as he is just a few short weeks away from facing off against Brock Lesnar inside Hell in a Cell. However, if you look at the concept of the character on paper, you wouldn't have been surprised to see it falling at the first hurdle. This is testament to Mark Calaway and the way he's been able to master the gimmick over the years. He and Paul Bearer were quite frankly the scariest characters on the card for many years, before pushing the envelope to new heights (or lows depending on your perspective) during the Attitude Era. We all know the backstory about how his parents were killed in a fire and how this shaped the man before he debuted in WWE back in 1990. This would see him kidnap his boss' daughter, try to sacrificially marry her and attempt murder many times over the next quarter of a century. Taker, of course, tried to bury man opponents alive, hang the Big Boss Man, and suffocate his former manager Paul Bearer in a bath of cement. His mind must have been to some very dark places. But we all still love him all the same...