#22 1988 (‘Hacksaw’ Jim Duggan):
The original Rumble match hasn’t aged well. As the first incarnation of the now-celebrated annual event, the 1988 edition featured many glaring flaws. It lacked in star power, had only 20 participants, didn’t feature any of the signature elements of the Rumble match (including music for the entrants), and didn’t have any long-term payoff for the participant.
Because of that, this Rumble fails to match many of its successors in terms of excitement but still ranks higher than others, due to its sheer novelty and historical significance.
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#21 2005 (Batista):
Despite serving as the metaphorical launching pad for the careers of two of WWE’s biggest rising stars at the time (Batista and John Cena), this match can only be remembered for three things. First, Daniel Puder getting chopped to death by Eddie Guerrero, Chris Benoit & Hardcore Holly in a little bit of dark comedy.
Second, Muhammed Hassan getting thrown out by multiple opponents.
Thirdly and most memorably, Cena and Batista screwing up the match’s finish, leading to an angry Vince McMahon running down to the ring and tearing both quads in the process. The visual of an angry Vince sitting on his ass as the referees try to figure out the finish is the only thing one should need to re-watch this Rumble match.
#20 1999 (Mr McMahon)
This entire match centred around the continued rivalry between ‘Stone Cold’ Steve Austin & Vince McMahon. It didn’t have any truly memorable moments outside of Austin doing his best to destroy Vince.
It didn’t really serve any purpose for Vince to win, other than to further put more importance on himself, despite being a non-wrestler. Whether you enjoy watching matches like this depends on whether you enjoy watching overbooked nonsense that is more about outlandish characters than anything else.