20 Worst WWE Matches Since 2000

8. Rosie O'Donnell Vs. Donald Trump (Raw - 8th Jan, 2007)

Kane Khali
WWE.com

Boredom, revulsion, hilarity, disbelief: the various matches on our list should provoke a variety of different response within the average viewer, but 'Rosie O'Donnell' vs. 'Donald Trump' should inspire just one:-

"Why?"

Just... "why?!"

For whatever reason, Vince McMahon decided that filling a small portion of his company's flagship show with a couple of impersonators sloppily brawling their way around the ring wouldn't be a complete waste of time. He was wrong. 'Donald' and 'Rosie' didn't look, behave, or sound like the celebrities they were supposed to resemble, and their 'match' soon had the fans chanting "boooooooring!" at a deafening decibel.

We're all used to McMahon's ill-advised horrendous comedic endeavours, but this might be the worst of all his attempts at making the crowd laugh, only to draw the opposite reaction. Trump won (because of course he did), and while WWE likely put this grand catastrophe together as means of capitalising on the public feud that still rattles on between the two celebs, even in 2017, Vince succeeded only in making a tit of himself, his company, and anyone daft enough to stay tuned.

Channel Manager
Channel Manager

Andy has been with WhatCulture for eight years and is currently WhatCulture's Wrestling Channel Manager. A writer, presenter, and editor with 10+ years of experience in online media, he has been a sponge for all wrestling knowledge since playing an old Royal Rumble 1992 VHS to ruin in his childhood. Having previously worked for Bleacher Report, Andy specialises in short and long-form writing, video presenting, voiceover acting, and editing, all characterised by expert wrestling knowledge and commentary. Andy is as much a fan of 1985 Jim Crockett Promotions as he is present-day AEW and WWE - just don't make him choose between the two.