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When the original Royal Rumble match happened in 1988, it was a twenty man battle royal (later to be changed to a thirty man battle royal the next year) and the winner was just for bragging rights. This continued on until 1993, where they officially made the winner of the match the #1 contender for the world championship at Wrestlemania. While it does make winning the Rumble maybe mean a little bit more, would it not be less predictable and thus more exciting if the match wasn't for a title shot but rather was just an annual event where everyone on the roster (the top 30 anyway, perhaps including the world champions like some of the original Rumbles did) got together and did battle with each other in a battle royal to see who could out last the other twenty nine men? Where there was a feeling every year that literally anyone could win it, no matter what their position on the card was?
Look at 1989. Randy Savage, the world champion, entered in the middle of the match and Hogan entered shortly after him. By the time the last eight or nine guys entered the match, both were already gone. (The way Hogan was eliminated was indeed interesting, he was very casually thrown out fairly by the Twin Towers after being double teamed, which is a good way of putting over how dominant a tag team can be. You'd never see some like the Prime Time Players, for example, eliminate Cena so simply in ANY battle royal like that today.) Anyway, after Hogan's elimination, there really was a feeling of how anyone could win it after that point.
With the title shot stipulation, there is usually little doubt as to who will win. I know that stip has led to some great moments in the past, like Shawn Michaels trying to win the 2010 Rumble to desperately earn the chance to clash with Undertaker again at Wrestlemania, which added a great deal of quality drama to the match and to that feud. Another example is Austin winning the 2001 Rumble to finally get a fair chance to reclaim the world title that he hadn't held in so long at the biggest stage of them all, or Cena winning this year, setting up his chance at getting redemption against The Rock this year, only with the world title on the line. But there's bound to be exceptions. Most years, I don't think it would have mattered, as the headline match of Mania could have worked out roughly the same anyway.
Anyway, it's fun to think about a Rumble where there really is the feeling in the air that anyone in the match could win (well, not anyone, but a whole hell of a lot more than when the title shot stip is in place.) Winning the Rumble is a good way to give someone a rub. It's also a good way for a heel to win since it's just a battle royal and doesn't require a pinfall or submission finish. Just look at how long a lot of heels in the past have lasted in Rumble matches of the past - Ted Dibiase in 1990, Rick Martel in 1991, Ric Flair in 1992 (who won), Kane in 2001, etc.
Look at 1989. Randy Savage, the world champion, entered in the middle of the match and Hogan entered shortly after him. By the time the last eight or nine guys entered the match, both were already gone. (The way Hogan was eliminated was indeed interesting, he was very casually thrown out fairly by the Twin Towers after being double teamed, which is a good way of putting over how dominant a tag team can be. You'd never see some like the Prime Time Players, for example, eliminate Cena so simply in ANY battle royal like that today.) Anyway, after Hogan's elimination, there really was a feeling of how anyone could win it after that point.
With the title shot stipulation, there is usually little doubt as to who will win. I know that stip has led to some great moments in the past, like Shawn Michaels trying to win the 2010 Rumble to desperately earn the chance to clash with Undertaker again at Wrestlemania, which added a great deal of quality drama to the match and to that feud. Another example is Austin winning the 2001 Rumble to finally get a fair chance to reclaim the world title that he hadn't held in so long at the biggest stage of them all, or Cena winning this year, setting up his chance at getting redemption against The Rock this year, only with the world title on the line. But there's bound to be exceptions. Most years, I don't think it would have mattered, as the headline match of Mania could have worked out roughly the same anyway.
Anyway, it's fun to think about a Rumble where there really is the feeling in the air that anyone in the match could win (well, not anyone, but a whole hell of a lot more than when the title shot stip is in place.) Winning the Rumble is a good way to give someone a rub. It's also a good way for a heel to win since it's just a battle royal and doesn't require a pinfall or submission finish. Just look at how long a lot of heels in the past have lasted in Rumble matches of the past - Ted Dibiase in 1990, Rick Martel in 1991, Ric Flair in 1992 (who won), Kane in 2001, etc.