15 Wrestling Nightmares Somehow WORSE Than Imagined

4. The Undertaker Hangs Big Boss Man

X Wrestling Nightmares Somehow WORSE Than Imagined Ric Flair Last Match
WWE

The fifth ever Hell In A Cell match also turned out to be one of the worst. To put things into perspective, The Undertaker vs. Big Boss Man at WrestleMania XV was the first pay-per-view HIAC since 'Taker's infamous (and almost deadly) epic with Mick Foley at King Of The Ring 1998. Mick is still walking around wearing the aftershocks of that one in 2025, and he revealed on 'Dark Side Of The Ring' that it'll haunt him for the rest of his life.

'Mania XV's effort will haunt those who watched it too.

It was so bad. Seriously. 'Taker and Boss Man ambled around for nearly 10 minutes with nothing to say, then the WWF unveiled their latest shock tactic. 'The Deadman' slipped a noose around his enemy's neck and Boss Man was hung from the top of the Cell structure by 'Taker's Ministry Of Darkness chums. It was ridiculously over-the-top, and it's kinda cringeworthy to see fans in the stands look on expressionless as the spot played out.

This didn't occur before the noise Vince McMahon and his creative types might've expected. In fact, it played before the most modest of pops as Michael Cole and Jerry Lawler tried their best to call for help. Boss Man's awkward flailing around gave way to apparent death, and...he was perfectly fine shortly afterwards. What was the point then?

Fans had maybe wondered what a feigned death scene would look like during the 'Attitude Era', and now they had answers. It sucked, and it hardly left an impression on anybody. Mercifully, Triple H and Foley would be along to rescue HIAC at No Way Out 2000.

Contributor

Lifelong wrestling, video game, music and sports obsessive who has been writing about his passions since childhood. Jamie started writing for WhatCulture in 2013, and has contributed thousands of articles and YouTube videos since then. He cut his teeth penning published pieces for top UK and European wrestling read Fighting Spirit Magazine (FSM), and also has extensive experience working within the wrestling biz as a manager and commentator for promotions like ICW on WWE Network and WCPW/Defiant since 2010. Further, Jamie also hosted the old Ministry Of Slam podcast, and has interviewed everyone from Steve Austin and Shawn Michaels to Bret Hart and Trish Stratus.