#4 Vince McMahon mocked Jim Ross' colon surgery (WWE RAW 24/10/2005)
As a trusted and loyal employee of Vince McMahon's, one would expect Jim Ross to be forever treated with the love and respect that he's earned over the years. However, that dynamic wasn't always the case. McMahon loved making fun of the commentator, with the biggest evidence of this behavior coming during a 2005 episode of WWE RAW.
A week after Ross had a colonoscopy in real life, the chairman of WWE decided to dedicate air time to a segment that mocked the surgery. McMahon played the character, Dr. Heiney and pretended to perform surgery on JR. It was tasteless when it aired, and it remains tasteless now
The seven-minute segment featured a prosthetic behind, which McMahon pulled some objects out of, including an American football and a goldfish. He even pulled out some Steve Austin merchandise, among other things. While the bit was designed to be funny, it truly wasn't.
Years later, during an appearance on Talk is Jericho, Ross stated that the main reason why he had an issue with the segment was that it made his wife, Jan, cry. Many fans have heard the sentiment McMahon has a pretty strange taste in comedy.