#2 Failed: Scott Hall
Before The Undertaker became the WWE and WrestleMania icon that we know him as today, he competed under the name Punisher Dice Morgan in New Japan Pro Wrestling in 1990.
During a series of matches for the promotion in March of that year, he teamed with Scott Hall to challenge Masa Saito & Shinya Hashimoto for the IWGP Tag Team titles.
Saito & Hashimoto regained their titles, while Morgan and Hall reinvented themselves and became known as The Undertaker and Razor Ramon in WWE.
Twelve years after their first televised match as a duo, ‘Taker teamed up with Hall (fka Ramon), as well as NWO member X-Pac, to face Bradshaw & “Stone Cold” Steve Austin in a 2-on-3 handicap match on Monday Night Raw in April 2002.
Once again, ‘Taker and Hall were unable to win, with the babyface duo of Bradshaw & Austin emerging with the victory.