Top 15 Inter-Generational Matches We Would Pay Big Money to See

Since no one owns a time machine (that I know of), we unfortunately won't be able to see some of the greatest "dream" matches that our minds can possibly come up with.  It's unfortunate that the likes

Since no one owns a time machine (that I know of), we unfortunately won't be able to see some of the greatest "dream" matches that our minds can possibly come up with.  It's unfortunate that the likes of Ric Flair, Roddy Piper, and Randy Savage will never suit up against the likes of Seth Rollins, Daniel Bryan (I don't think I'll ever get over his retirement), and Kevin Owens. Would we pay big money for some of these dream matches? Absolutely! So much that I would risk not watching WWE television for a full year just to see some of these dream matches.

Sure, we've seen John Cena take on Ric Flair in the past, but imagine if it was in Flair's prime?  That would be something we'd be more interested in.

We've taken some of wrestling greatest heroes from every era and imagined what it would be like had they gone up against each other in the physical primes of their career. Some of them COULD happen, pending on if we throw the retirements out the window, but for now, let's stick to imagining a perfect world where every one was still in their prime.

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15 Andre the Giant vs Big Show 


Not only are they the two biggest superstars to ever lace up a pair of boots, but Big Show was once called the son of Andre the Giant earlier in his career. Seeing these two lock up would mean over 1,200 pounds of man in peak physical condition.

Don't get us wrong, this wouldn't be a very exciting match, but the slams and punches thrown would be impressive an violent. That would mean a match that every spectator watching would keep their eyes glued to just to see who falls first.

Heck, even make it a last man standing match to find out who the greatest giant in wrestling history truly is.

14 Charlotte vs Trish Stratus /

This one could go down as the greatest women's match in WWE history if Trish was 10 years younger. Trish was the most physically impressive Diva on the roster during her time and now the same goes for Charlotte.

Having said that, these two could easily main event a PPV if given the chance and tear the house down. Throw in a Chick Kick from Trish and a spear from Charlotte, and the image of Charlotte having Trish locked in the Figure Eight would draw major money.

13 nWo vs The Shield /

They both took out everyone in their path. Now who'd pay to see two of the greatest factions in wrestling history face off. Imagine the image...

Hogan faces Ambrose, Hall faces Rollins, Nash faces Reigns. All three in the middle of the ring. TAKE MY MONEY NOW!

The buildup to this match would be one for the ages. These two teams would irritate each other to no end that it would make The Shield's feud with Evolution look tame.

While on paper, the nWo stacks up more on physical weight, the theatrics of all three members of The Shield (Rollins more than anyone) makes this matchup so great, that you would not be able to take your eyes off this one.

12 Chris Benoit vs Daniel Bryan 


A promo for this match wouldn't be needed, as both men both proved their worth as in-ring competitors and weren't really exciting talkers. This match would work simply because both are considered among the best technical and pure wrestlers of all time.

Had the truly unfortunate events not happened with Chris Benoit, and if Daniel Bryan was able to stay full healthy, this matchup could have been a reality a few years back, possibly in 2010, if Benoit was up for it.

11 Jake Roberts vs Randy Orton 


Talk about a matchup of head games. These two are known as two of the most conniving wrestlers when working in the ring.

Slow and methodical, each man would tear the other apart and have no remorse doing it. While the match would truly be slow, grueling, and a wonder to watch, a fast RKO or DDT finish from either man would erupt the house.

Plus, who wouldn't want to see Jake the Snake put his pet python, Damien, on The Viper's face?

10 CM Punk vs Kevin Owens 


We would honestly just pay for the promos and build up for the match. Hell, we would pay for just ONE promo between these two. Known for holding nothing back on the microphone, Punk and Owens would create magic working with one another. Not to mention that these two are also fantastic in ring competitors, but let's go back to the build up.

Separate interviews from both men would create the friction needed to book a match of this caliber. If Punk decides to ever come back to professional wrestling (don't hold your breath), this would be the one match that should be booked for him to come back to.

9 Edge vs Bret Hart 


Two of Canada's greatest wrestling exports colliding in a ring would not only be great for wrestling, but also for the country of Canada, who are well known for the talent they bring to wrestling. On top of that, Edge and Bret Hart are truly special.

While not being known for being charismatic, Bret Hart never was one to hold his true feelings in. Known for lashing out against people who wronged him, Edge could be someone that would get on Hart's bad side as The Rated R Superstar was one of the very best at generating heat.

They could go with a storyline of Hart saying that Edge is tainting people's views of Canada and this could ultimately be a battle of respect and national pride.

8 The Undertaker vs Sting 


Two of the most iconic figures in wrestling history, and the flag bearers for their respected brands, THe Undertaker and Sting actually made sense for this year's WrestleMania and was actually close to being booked.

It made all the sense in the world. The Undertaker's potential last match happening in his home state of Texas, Sting finally signing with the WWE, and both being locks for the WWE Hall of Fame (Sting being inducted this year). But what went wrong?

WWE decided to put Sting in a pointless feud with Seth Rollins back in September for the WWE World Heavyweight Championship. Had this feud never happened and if Sting never got hurt and forced to have surgery, this match between Taker and Sting could have actually happened. Or they could have just booked it last year, instead of Triple H vs. Sting.

7 Mankind vs Bray Wyatt /

Both awesomely unique, a match between these two would be an entertaining one. Mankind being what he was and with Wyatt being what he is, they compliment each other so perfectly that it would almost be too good to be true. The weirdness of both characters go together in a formula only destined for success (in our minds).

Also, bringing back unique matches, such as a Buried Alive match, would only heighten the rivalry that these two could have against each other. While Mankind has already competed in a Buried Alive Match, Wyatt would be a perfect addition to this match history and the build up to this clash would be one that would be remembered for a long time.

6 Daniel Bryan vs Shawn Michaels 


Everyone thought that this was going to be a real thing back in 2013 when Michaels superkicked Bryan out of the WWE Championship, and man would it have been great.

They are two of the greatest storytellers to ever step inside of a wrestling ring and it would create magical moments that no other superstar would be able to create. However, we wouldn't want to see it happen with a 50-year-old Shawn Michaels.

Give us a mid 90s Shawn Michaels against a fully healthy Daniel Bryan. Michaels, being the flamboyant and arrogant superstar and Bryan, being the no nonsense hard worker, would create a feud that would rival any other in WWE history.

5 Roddy Piper vs Dean Ambrose 


Both play on-screen lunatics. They compliment each other so nicely and resemble each other so much in style that it would make sense that if Piper were a superstar today, his persona would be comparable to Dean Ambrose's.

Ambrose would have been the perfect guest on Piper's Pit, as both he and Piper have so many unpredictable qualities that it would be must see television.

Inside the ring, both would unleash their highly aggressive sides and if the situation presented itself, Piper would try and cheat to win. Against a guy like Piper, Ambrose would have to be on his toes.

4 Stone Cold Steve Austin vs John Cena 


We would be more excited by the cheers Austin would get and the boos Cena would get rather than the actual match. That arena would be the loudest of any arena in WWE history, as there would be chanting going on for the entire match and, with these two, the match would probably go on for around 30 minutes.

And there would be no slowing these guys down.

Known as two of the hardest workers in WWE history, Austin and Cena would put on a match for the ages. Whether you are a Cena fan or not, you have to respect his work ethic and against Austin, and with all the fans mostly likely backing The Rattlesnake in that match, Cena would have to put on the performance of his life.

3 Batista vs Brock Lesnar 


The Animal vs The Beast Incarnate. This id something we're sure a lot of people were looking forward to when Batista made his WWE return in 2013. However, it never came to be. Batista ended up winning the Royal Rumble and main eventing WrestleMania that year, while Lesnar would feud with The Undertaker and those two would infamously face off at WrestleMania XXX.

It's almost baffling that these two never faced off as established talent (if you don't count their time together in OVW). It would make sense as they were two of the best "genetic freaks" that WWE had to offer when they were both starting off in the WWE in 2002.

IT would surely be a hard hitting war and any time you can add Paul Heyman to a feud it automatically builds the fire. WWE missed out on Brock vs. Batista, as it could have gone down as one of the best ever.

2 Jeff Hardy vs Seth Rollins /

This match of old school and new school daredevils would no doubt be an automatic money maker if Jeff were to come back to WWE for one last run.

However, Jeff Hardy is obviously not the same wrestler as he was 10 years ago. He's been hurt, as being sent through tables and jumping off of ladders takes a toll on your body that is tough to come back from.

That's why we're talking about early 2000s Jeff Hardy taking on modern day Seth Rollins in what would be a high flying spectacle, a match that would be talked about for years. Rollins has already established himself as one of the best workers in the WWE and a match with Jeff would be a sort of symbolic passing of the torch between these two daredevils.

1 John Cena vs Hulk Hogan


It's only fitting that the two biggest wrestling personas of their time would be an instant dream match up. While both wrestlers in their prime were not the best in ring technicians, the fandom they created can never be duplicated.

It seems like every year at WrestleMania time, we hear about rumors of a Cena-Hogan match, however it never comes to fruition. Due to the recent Hogan scandal, it now seems that this match may never happen at all, not that there was a huge window for it anyway.

With the leader of the Hulkamaniacs and the leader of the Cenation coming together for a once in a lifetime match, the two faces of their eras would instantly be a main event draw that any wrestling fan, whether or not you are a fan of Hogan or Cena, would watch due to the legacy of both performers.

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Top 15 Inter-Generational Matches We Would Pay Big Money to See