As 2006 rolled around the Undertaker had his sights set on the World Heavyweight Championship, a title exclusive to Smackdown. The Undertaker challenged Kurt Angle. At this point, Angle and the Undertaker had great in-ring chemistry. Despite returning to his Deadman gimmick, the Undertaker proved he could wrestle and compete in an athletic affair against the amateur skills of Kurt Angle. Angle accomplished a rare feat by pinning the Undertaker clean.
In the rematch , Mark Henry would make his presence known by costing the Undertaker the title. This would lead to a Casket Match between the two at Wrestlemania. Henry vowed to end the Streak but like 13 before him, he fell too and was rolled into the casket. Following these events on an episode of Smackdown, the Undertaker was attacked by a colossal giant named the Great Khali. The Great Khali would defeat the Undertaker in the middle of the ring in convincing fashion. Their feud would culminate in a Last Man Standing match where the Undertaker would prove that he could continue to slay any monster in his path as his track record would show.
In the final months, the Undertaker would take on newcomer Mr. Kennedy. Kennedy, like Orton the year previous, would look to have all the components to make a future star. Kennedy would pick up a few victories over the Deadman, some with the assistance of MVP who had been feuding with Kane. This led to a reuniting of the Brothers of Destruction as they would decimate these newcomers. Kennedy eventually fell to the Undertaker in a Last Ride Match, where the Undertaker had to pull out all the stops to defeat Mr. Kennedy. Once again, the Undertaker proved that stepping in the ring with him could lead to success for the opponent standing across from him. Would other superstars take note and dare challenge the Undertaker for a chance at superstardom?