#1.) Alliance with The Undertaker
The Big Show debuted in WWE in 1999 as a heel, turned face a month later. A few months after that, he would form a surprising alliance with The Undertaker where he would win his first two tag team titles with the WWE. Though the alliance didn’t last long (due to Undertaker’s injury), it certainly was the most memorable heel turn of The Big Show’s career.
It happened during the peak of the Attitude Era and he would find his way in becoming one of the biggest stars of the company at the time.