10 Crazy Wrestling Gimmicks That Should Have Never Worked (But Did)

2. Undertaker

There is really just no way that this should have worked. And yet, it's one of the most successful and beloved gimmicks of all time. For starters, just what is The Undertaker? Is he an actual undertaker? Is the "dead man" zombie description supposed to be literal? Both? In an era filled with all sorts of cartoon-like characters for wrestling, Undertaker was just the right cartoon character at the right time. As the Supermans and Flashes of the wrestling world were wearing thin, Undertaker was essentially the Batman among his peers, bringing an element of counter-cultural darkness that children of the 90s so craved to the forefront. Undertaker also brought an element of mystery and intrigue, enhanced further by the "powers" he seemed to demonstrate as arenas darkened and grew colder by his very presence- or his entrance, at least. Mark Calaway not only fully embraced a gimmick that would probably be doomed to a very short shelf life in nearly anyone else's hands, but he evolved it over the years as well. From zombie(?) to a Lord of Darkness to a cult leader to a demon among us, the Undertaker has endured. Even during the stint from 2000 to 2003, where he became an "American Badass" biker, he held the name and the roots of his character close to him before returning to the darkness which birthed him.

The Undertaker has been wrestling under that guise since 1990, nearly 24 years as of this writing. In that time, he has won numerous accolades along with his four WWE Championships, three WWE World Championships, six WWE World Tag Team Championships, and one run each with the WWE Hardcore Championship and WCW World Tag Team Championship. However, as many know, Undertaker's success goes well beyond any championship to an honor he and he alone possesses: A winning streak of 21 victories at WrestleMania. Upon hitting a certain point in his career, the chance to break The Streak was worth as much- perhaps even more- than any title shot one could have at the Showcase of the Immortals. Though Brock Lesnar broke The Streak at WrestleMania XXX, it is widely believed that no one will ever equal it, making Undertaker more than a success, but a legend in his own time.