Now that The Undertaker's famous undefeated streak has ended, we can now look back it in its entirety. In the days leading up to WrestleMania 31, we will take a look back at every memorable chapter of the feat that can never be duplicated. Here's a look at what became the holy grail of professional wrestling.
The Undertaker vs. Big Boss Man (8-0)
WrestleMania XV | First Union Center (Wells Fargo Center) — Philadelphia | March 28, 1999
Match length: 9:46
The year 1999 saw another transformation for The Undertaker character. When he first debuted in the WWE, he was essentially an unstoppable zombie that simply followed the orders of Paul Bearer and lacked any real depth as a character.
By the mid-1990s, The Undertaker began to speak and eventually became a solo act, lending to his depth and increasing popularity.
By 1999, The Undertaker had reunited with Bearer, but was not the silent zombie following orders. He was a demonic cult leader that called himself the "Lord of Darkness." A change to his music and some slight changes to his look to make resemble Satan himself made for a very cool heel character on WWE television. For the only time of his career, The Undertaker led a faction that he dubbed his Ministry of Darkness, and they played a role in his Hell in a Cell match against Big Boss Man at WrestleMania XV.
Unfortunately, the match was a bit of a letdown, especially considering its placement on the card as the semi-main event.
The ingredients were in place to make this proverbial meal delicious. Both The Undertaker and Big Boss Man were talented veterans that were more than capable of putting on an entertaining match.
You put these two inside of a Hell in a Cell and it should only increase the entertainment value.
But for multiple reasons, the finished product left a bad taste in people's mouths.
The main problem with this match was that it wasn't necessarily worthy of being inside a Hell in a Cell. Usually, the Cell is saved for blood feuds that played out over the course of months. The Undertaker and Big Boss Man had a decent feud going, but it wasn't worthy of coming to a climax inside the Hell in a Cell.
The match itself wasn't worthy of being the semi-main event of the show either. Clocking in at just under 10 minutes, it probably would have been better served if it had been given more time so that the two men could make better use of the structure itself.
Nothing on this night would have topped the main event between The Rock and Steve Austin, but it could have been a nice side dish to the main entrée.
The Undertaker won the match in a rather uneventful fashion, which set up the most infamous moment of the proceedings when Brood members Gangrel, Edge and Christian descended from the rafters to help hang Big Boss Man from the Cell.
Not only was this somewhat offensive, it was highly unrealistic. In storyline, The Undertaker was essentially murdering Big Boss Man in front of nearly 20,000 people. No one was going to believe that was happening, which would nullify any reason to do it.
At the end of the day, not only was the probably the most forgettable match in The Undertaker's streak, it arguably the worst Hell in a Cell match to date.
This was The Undertaker's lone appearance at WrestleMania as the demonic cult leader and his last as a heel. He's been a babyface ever since. Unfortunately, it didn't come off nearly as memorable as it should have.