20 Most RANDOM WWE Royal Rumble Entrants

1995 is roundly considered the weakest Royal Rumble ever, but 1996 has just joined the chat and would like to put forward its own case for that dubious distinction. Shawn Michaels won it for a second year running, and his star power was bolstered by the likes of Owen Hart, Diesel, The British Bulldog and debuting new monster Vader. If one's being charitable, a fading Yokozuna and old warhorse Jake Roberts helped too.

Then, there was USWA man Doug Gilbert. Yeah, he didn't really fit in.

Gilbert's brother Eddie had earned plaudits for his work before passing away aged just 33 in '95. Perhaps he'd have been a better fit for the paper-thin WWF ranks than his sibling, because poor Doug looked so out of place next to stars like HBK and Vader. It was the new heel hopeful who punted Gilbert from the match too - Doug got three minutes to show everyone what he could do, and he was eager to stake a claim for why he should be part of the 'New Generation'.

Looking back, there was an indy vibe to a lot of what was going on across both Rumbles in 1995 and 1996. Gilbert's arrival reflected that, because he was never realistically going to win fans over. After the pay-per-view, Doug received another tryout as part of a co-branded WWF/USWA event in February. Being fair to the dude, he's been working pretty much nonstop ever since, and was last spotted on GCW and NWA cards in June 2023.

It's hard to imagine those in charge of fed recruitment were impressed in '96.