15 Biggest Matches WWE Should've Booked In The 90s (But Didn't)

8. Bret Hart vs. Jake The Snake (1992)

Rumors have a Bret Hart vs. Jake The Snake feud as one that was penciled in for 1992 but it obviously never materialized. Bret has said that he remembers being told that he would be going into a program with Jake but then Roberts "went and got himself fired" putting an end to any plans they might have had. A Bret Hart vs. Jake Roberts feud would've been an instant classic as these two men's wrestling psychology and match ability were second to none. Jake would've likely been the next to put over the Hitman as Bret was quickly rising to the top of the WWE, but the exact timing of the scheduled feud is not clear. Jake turned heel in the Summer of '91 and feuded with Randy Savage in an all-time classic rivalry. Their feud led to a Jake vs. Undertaker match at WrestleMania VIII and perhaps, Bret may have been in line to battle Jake later that year. But Jake demanded (and received) his release from WWE immediately after WrestleMania VIII. Jake was expecting to fill Pat Patterson's recently-vacated position on the creative team, but was disappointed when he was told just prior to WrestleMania that the seat would not be filled "out of respect to Pat". Patterson had stepped down after allegations of scandals involving young ring attendants surfaced. Bret Hart vs. Jake Roberts, especially a heel Jake Roberts challenging for the WWF Championship is the stuff of legend. Unfortunately, it exists only in fans' minds as this one never came to fruition.