Undertakers career is definitely legendary, maybe the most legendary next to Andre the Giant. However, other than his last few years, which thankfully did end on a high note, what year would you consider his lowest point when he was fully active? To me, I always
lean on 1999.
I think it was King of the Ring 2002 when he and HHHH were having a plodding borefest to determine who was going to heroically carry the promotion when the real stars were gone.