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2017 was pretty weird.

Goldberg as the World Champion at Wrestlemania.

Jinder Mahal as WWE Champion out of no where.

Jason Jordan is the son of Kurt Angle.

House of Horrors and Punjabi Prison matches.

Pumpkin Demon vs Sister Abigail.

Undertaker retired except he didn't.

Cruiserweight segments main eventing Raw with Enzo Amore.

There's probably way more stuff in there.
 

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Great post! 1993 was definitely a year where Vince was in panic mode after all his 80s stars were either gone or had one foot out the door. He also had the impending steroid trial staring down at him.

Safe to say 1993 was probably the worst professional year for Vince since he bought the company from his dad
 

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Agreed! 1993 was the "drizzling s**ts"! 1995 was horrible as well, but 93 definitely was "weirder".
Weird is a very broad term so I do not know what type of answer you are looking for. I will take a stab at it by weird booking. I will go with 1993.

1993 saw the end of the Hulkamania era in the WWF. Booking throughout saw "weird" things such as:

Macho Man trying to pin Yokozuna in the Royal Rumble

A career vs. career match on free tv instead of Wrestlemania (Perfect vs. Flair)

Wrestlemania held in a parking lot with everyone wearing togas

Hogan winning the title in am unscheduled match at the end of Wrestlemania then disappearing for a couple of months

Hogan losing a match and the title by someone doing a leg drop on him

A jobber (123 Kid/X-Pac) win a match against an established star

A star being built up to be the replacement for Hulk Hogan (Lex Luger)...then celebrating with confetti and balloons after winning the title match by COUNTOUT!!!

A heel champion with a long run (Yokozuna)

Randy Savage on commentary

Gene Okerlund and Bobby Heenan leaving
Joe Fowler, Todd Pettengill, and Bonnie Blackstone replacing Mean Gene Okerlund, Lord Alfred Hayes, and Sean Mooney as the backstage interviewers. I remember Fowler more for hosting Maximum Drive than the WWF or the infomercials he's hosted in recent years. Fowler and Blackstone would both be replaced by Stephanie Wiand and Stan Lane....
 

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I think in terms of what you described (stop-start pushes, atrocious nonsensical booking, backstage fuckery etc.), 1993-1995 instantly come to mind. Besides the sexually ambiguous androgyn Goldust Gimmick, Giant Gonzalez, Chloroformed Undertaker, Mabel's push, occupational gimmicks, Goobledeegooker, the many faces of Doink etc., the main event/FOTC scene was a mess after Hogan and UW left a massive vacuum in their wake. Flair, Luger, Nash, Hart, Michaels, Taker all couldn't move the needle in any significant way (Hart less so internationally).
 
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