#2 Giant Gonzalez
Until Brock Lesnar beat The Undertaker to end the streak, it was Giant Gonzalez who came closest to breaking the streak. Vince McMahon trusted Undertaker to get the big man from Argentina over at WrestleMania 9 but even the Deadman couldn't get the lumbering Gonzalez over.
The Argentinian was very immobile and struggled to do even the most basic of wrestling moves. Despite this, The Undertaker only won the match by DQ after Gonzalez used chloroform during the match.
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#1 Roman Reigns
Before you get your pitchforks out, let me do some explaining. Yeah, Roman is great inside the ring and one of the top stars right now, that does not negate the reaction his match and victory against The Undertaker at WrestleMania 33 got.
Of course, it was the right decision for Reigns to beat 'the Deadman', but that doesn't negate the fact that the Undertaker failed to get Roman Reigns over with the majority of the WWE Universe, at least, the section of the fans WWE needed him over with.