#2: Rob Van Dam
Fans may be scratching their heads thinking of a time when RVD was heel, but it did indeed happen (kinda) in the WWF.
Joining the company in 2001, Van Dam came with a wealth of fans from his time in ECW, so it seemingly made sense for the Extremist to join the Alliance: a consortium of WCW and ECW stars.
The only problem, was the Alliance was a heel group and no-one could really boo RVD.
Though Van Dam remained loyal to the Alliance (even participating on their team in the Survivor Series winner takes all match), fans simply refused to boo this so-called heel.
Eventually, commentators Jim Ross and Paul Heyman had to reference how despite being an Alliance member, Van Dam was beloved by the WWF crowd, as his so-called heel turn was dead on arrival.