Between Judgement Day 2000 and Survivor Series 2003, The Undertaker ditched his 'Deadman' persona and began wrestling as a permanently disgruntled biker. It was an incredibly bold decision, especially considering the immense popularity his previous gimmick had built up over the years. Like a middle-aged dad undergoing a mid-life crisis, The Undertaker made some curious choices. He started wearing bandanas and sunglasses, and rode a motorbike to the ring. He embraced horribly ill-fitting entrance music by Kid Rock and Limp Bizkit. He started referring to himself as the "big dog", and his feuds centred around an over-the-top anger at younger superstars for trespassing on his "yard". Nowadays this period is mostly skirted over when considering Taker's legacy, like Shawn Michaels "losing his smile" or Austin's refusal to put over Brock Lesnar. As mentioned, the gimmick change was a very brave idea - but that doesn't necessarily mean it should be commended. The Undertaker's biker persona was an unquestionable low point in his career, and could have caused irreversible damage to his legacy had it not been wisely scrapped.
7. His Return Immediately Sucked
Any superstar of the Undertaker's immense popularity will always fetch a massive pop upon making their return. After eight months out with an injury (during which time he reportedly rejected a WCW contract), Taker's Judgement Day 2000 return was understandably well received - but there was just one problem. Its booking made very little sense. With Triple H and The Rock tied at 5-5 in their titanic Iron Man match, The Undertaker debuted his 'American Badass' gimmick, roaring to the ring on a motorcycle and attacking the Game. The crowd went wild, only for the referee to award a fall via DQ to Triple H. Undertaker, the returning babyface hero, had inadvertently handed The Rock's WWF Championship to the biggest heel in the company. If such a confusing, cheap finish occurred today, it would rightly be panned, but Undertaker's eagerly-anticipated return overshadowed the weak nature of the booking. However, when realistically looking at the effects of the return, it's clear that nobody emerged stronger as a result. The Rock lost his belt; Triple H came across as a lucky champion, handed the title on a fortunate DQ fall; and Undertaker seemed incredibly foolish for causing such a title change, especially given his baffled expression as the PPV went off air.