1999 might have had a lot of trash, but it was still entertaining television overall and that's all that matters to me. IMO, the worst year in history is 1995, easily. Anyone who thinks otherwise, please go and watch 1995 from beginning to end and tell me your opinion is still the same. And if you wanna bring objectivity into it, '95 was also the worst year financially for the WWF as well. I'll sum it up:
1. Diesel was turned from an edgy, bad ass powerhouse character into a typical vanilla baby face with no edge to him whatsoever.
2. The main event scene was dry as hell. When your main event is so lacking in star power that you have to rely on the likes of Tatanka, Mabel, Sid Vicious and Bam Bam Bigelow (the latter of who was a good talent, but main event level at that time?) to headline, you know you've got a shitty roster on your hands.
3. Bret Hart, who had just had a great run as world champion a year before (as well as being involved in one of the all-time great feuds imo with his brother Owen Hart) was now suddenly feuding with a pirate who stole his jacket and a non-English speaking Japanese guy with a bunch of writing all over his body. Um... what?
4. Waylon Mercy debuts as a pretty interesting character who stood out for being just different from all those around him, but he ends up being wasted.
5. Just all kinds of bad angles and matches all across the roster. Just a severe lack of star power all around this year. (Mabel was KOTR that year... enough said.)