When Ric Flair returned to WWE in December 2001 as the co-owner of the company, he didn't intend on wrestling much. His confidence was shot after the final painful WCW years and he really didn't think he belonged in the ring anymore, as he explained in his 2004 autobiography. But he got roped back into doing high-profile gimmick matches, including a Street Fight with Vince at Royal Rumble and a No DQ match against The Undertaker at WrestleMania X8. The match with 'Taker came about as Flair (as co-owner) was disgusted with his underhanded tactics, so much so that he cost The Undertaker his match with The Rock at No Way Out. Undertaker challenged Flair to a match, but the Nature Boy refused, saying he was now an owner and not a wrestler. In order to lure him back into the ring, 'Taker began taking out Flair's family and friends, including Arn Anderson and his son, David. Flair eventually accepted and the match was on. The two had a really engrossing brawl, which was especially good when you consider Flair's mental state at the time. Undertaker won, of course, extending his streak to 10-0.
