10 Biggest Regrets From The Undertaker's WWE Career

For the longest time, The Streak wasn’t exactly known for churning out instant classics. Granted, ‘Taker did have unforgettable showdowns with Kane, Triple H and Ric Flair, but for every barn-burner there were at least two glacial affairs with the likes of Giant Gonzalez or King Kong Bundy.

‘The Phenom’ needed something to change so, with his epic series of matches against Randy Orton seemingly inspiring him, he decided it was time to have a legendary WrestleMania match against someone he knew he had chemistry with - Kurt Angle - and he was even willing to lose to make it happen.

He and Angle pitched the idea to Vince McMahon but the Chairman declined and instead saddled ‘The Deadman’ with a Casket Match against Mark Henry.

‘Taker desired to show us what he was truly capable of at the Showcase of Immortals and he was given the exact opposite of what he wanted in the type of ‘Mania match he was trying to move away from. Yes, he’d finally get opportunities to showcase his talents in his subsequent WrestleMania classics, but you can bet that ‘The Deadman’ was a little miffed that he was forced to relive his dark days in 2006.

After his incredible World Title match with Angle at No Way Out - hey, at least Vince gave them that, right? - it’s clear that ‘Taker should have gotten his wish.