3. Dr. Heiney
As part of WWE’s lengthy quest to find an adequate replacement for Jim Ross, they had made a habit of embarrassing Good Ol’ JR, removing him from TV, then bringing him back when they realised that nobody could touch him for sheer talent at the announcing desk. One of the most insensitive instances of this was when JR needed time off for colon surgery, which was needed to prevent a potentially life-threatening medical condition.
While JR was recovering from said surgery, Vince McMahon went on Raw and starred in a skit in which he, as Dr. Heiney, performed surgery on a crude puppet wearing JR’s trademark hat, removing various objects from the patient’s behind, including a bottle of JR’s BBQ sauce, a hand, and JR’s own head, all intercut with audio clips of JR’s commentary.
The entire segment was intended to make light of a serious medical condition being suffered by one of WWE’s longest-tenured employees, and was almost universally despised immediately after airing. Mick Foley said it best in one of his autobiographies: the only person who found it funny was Vince McMahon himself.