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This is a "Wild Mass Guess" entry, where we pull out all the sanity stops on theorizing. The regular entry on this topic is elsewhere. Please see this programme note.
Mario Kart
So, what's the deal with Go-Karting with Bowser?

It's all that crazy Mushroom Kingdom Royal Family politics, man. Truth is, Bowser's species came to Mario World millions of years ago on an asteroid named Bunuri, and they were the dominant species on the planet. But Mario World changed from a lizardy, cold-blooded place into the beautiful fungus-covered paradise it is today. The Koopas retreated beneath the surface, except for a few of their leaders, who interbred with humans in order to control the population.

These half-Koopa, half-mushroom people became the Royal Family, and continued to breed with the Koopa leaders until they all died out, because they were all intermarried with the Mushroom people. But something happened with the Koopas beneath the surface, and they became the violent, militaristic people they are today, and Bowser, the son of some nothing noble of a minor Koopa Kolony, overthrew his cousins' family and instated his own Military Junta, and proceeded to try to take the surface world.

The reason Bowser wants to kidnap Peach and Daisy, is because if he marries one of them, his children will be in line for the Mushroom Kingdom throne.

As to why it keeps happening, well, here's the thing... Bowser's got an inside man, who is part mushroom, part reptile. He's immensely trusted by the royals, and is such a deep cover agent that he plays himself as a huge coward and an idiot, in order to hide the fact that his allegiance is purely Koopa. But his name gives it all away: Why do you think he's called "Toad"?
  • Toads are amphibians...
  • And I do believe that the various Mushroom hat wearing people are given variations of the name "Toad". (Toadsworth being one example.) If one person can be considered a inside man because of the name, then what keeps the other people from being the same?
  • I'd always figured it was because Mario is a very poor judge of character and just thinks Bowser is his worst best friend.
  • I've always figured Bowser was only evil because he was under the influence of the power stars (like Wiggler in Super Mario 64). I just figured the Mario Kart games took place before he was corrupted, or after he shook the addiction.

The games are a test to see how far we can go before we lose it.

This explains why the cheating is so bad. Nintendo wants to see how far we can go before we lose our sanity due to cheating bastard AI. The game doesnt even try to hide it that well on some versions of mario kart. On 50 Cheating Capacity, your more likely to make it through the whole game. On 100CC, your gonna need antidepressants. on 150CC, if you get through this alive, you need a mental hospital. This also explains the rubberband AI and how the CPUs coordinate attacks on only you.
  • Or maybe it's to see how far the player can push themselves to beat the worst opponents out there, almost like a training montage.
Dry Bones in Mario Kart DS is the Koopa from Super Mario Kart and Double Dash.

In between Double Dash and DS, he died and was reanimated as a Dry Bones. However, he still had a passion for kart racing, so he came back. The Koopa in Wii is his relative.
  • Better idea: the Koopa of Super Mario Kart loved karting immensely but when Wario stole and redesigned his kart (this part isn't WMG, it actually says in the Mario Kart 64 manual Wario stole the kart), he got depressed and and killed himself after he wasn't allowed to enter the Super Circuit. Unfortunately, he was granted permission for Double Dash since the Pipe-frame Karts were thrown out, so a relative took over for Double Dash. The relative needed a break for a while, and the old Koopa was resurrected and therefore was ready for DS. In Wii, the relative was done taking a break and Dry Bones just had to come back again.
  • The relative could have swapped places with Dry Bones for 7.

Koopa The Quick is the Green Koopa Troopa in all the Mario Kart games

Koopa The Quick clearly likes racing, it simply makes sense with his character. The Super Mario Kart predates his introduction technically, but that's a minor issue.
  • Easily explained, too: In Super Mario 64, his love of racing drove him to try out foot-racing. After seeing how handily Mario beat him, however, he decided to stick to kart racing.

Rainbow Road is the cause of the Kart Races

Every few years, it pops up in the general vicinity of space in a new form. Whether it's a sentient deity or the Mushroom Kingdom people just choose too, a Kart racing tournament is held in its honor, the last race taking place on the road itself.

Neo Bowser/Koopa City takes place in a Bad Future where Bowser succeeds in conquering the Mushroom Kingdom.

It could even be Mushroom City, renamed and rebuilt in Bowser's honor.

Mario Kart 7 will get Downloadable Content.
DLC for 3DS games has been confirmed as a feature.

Nintendo is aware of the many cries of "ruined" over the lack of some fan-favorite characters, possibly because they wanted to bring more attention to the four newcomers. DLC in the form of veteran racers remedies this. Don't think Nintendo forgot about those guys, either; they'll be playable in upcoming entries in the spin-off titles (Mario Party 9, Fortune Street).

Are you disappointed with the current roster? Were you clamoring to play as Waluigi, King Boo, and Dry Bones? There's still hope. As an added bonus, DLC for 3DS games will be free of charge. In the end, everyone wins.

After all, why have Waluigi Pinball if the purple guy himself can't race on his own track? The late November 3DS system update will add the ability for developers to release downloadable content for games in the 3DS eShop, but Nintendo president Satoru Iwata has revealed there'll be no Nintendo DLC until 2012.

Speaking to investors after the semi-annual financial report, Iwata said:

Nintendo will also offer something like this for the titles Nintendo publishes next year, in a way that should be appreciated by our consumers.

That means we most likely won't see any extra cars or courses in Mario Kart 7 for example, but we could see additional stages offered in Luigi's Mansion 2.

No actual quote from Nintendo. Plus the author said "most likely won't". Emphasis on "most".

Metal Mario is Bowser's answer to Metal Sonic.

  • Like Eggman, Bowser decided to make an Evil Knockoff of the main character. Metal Mario in Mario Kart 7 is Bowser's new Dragon.

  • By extension, Metal Mario is an Early-Bird Cameo for his appearance in the next mainline game, as he has never appeared in a Mario game since Dr. Mario 64. It helps he's been depicted in recent spin-offs as Mario's rival.

The entire Mario Kart franchise is an epilogue to the Super Mario series.

  • After the countless conflicts between the Mushroom Kingdom and the Koopa Troop, as chronicled in the plaforming games. the two sides made a treaty that guaranteed the coexistance of the two parties. As a celebration of the peace, a karting tournament, similar to the Olympics, was held. The leaders of the two factions agreed to compete themselves, along with the Mario brothers, two athletes from each faction, and two foreigners, Yoshi and Donkey Kong Jr. The tournament was held throughout both countries as a sign of unity. Even Bowser's mighty fortresses now became a sign of unity and cooperation. The entire affair was a success, and future tournaments would be held every few years.
    • Following tournaments expanded even further, including important dignitaries from a variety of nations. Notable examples include Donkey Kong from Donkey Kong Island, Princess Daisy from Sarasaland, Rosalina from Comet Observatory, and Queen Bee from Honeyhive Kingdom. As this occurred, locations from their kingdoms were also modified into race tracks. Eventually, old tracks were reused as parts of new tournaments.
      • For the record Donkey Kong Jr from Super Mario Kart is the canonically the same character as the Donkey Kong in the current games. So there must have been a LONG time between games.
    • Also, they reinvented the time machine from one of Mario and Luigi`s past adventures, and enhanced it so it could travel in between dimensions, too. Hence Neo Bowser City, another dimension where Bowser rules, and Rainbow Road.
      • Unless Neo Bowser City is just an indication of how much Bowser's rule has thrived in the many years since the races started an era of economic success.
    • Alternatively, Rainbow Road is the love and harmony the treaty brought about given physical form through the will of the Power Stars. It started off as a barebones track of rainbow bricks, but as more and more people joined the races, spreading the harmony across more and more kingdoms, the road grew in size and detail, even incorporating warm memories of the past. (Everyone showing up as neon faces in the stars in 64, and the floating rainbow statues of items in Double Dash) Once Rosalina joined, as a sign of thanks, she combined her cosmic powers with the power of the stars to allow Rainbow Road to grow to epic proportions, incorporating her own star fueled interstellar technology to let racers travel all around the Mushroom Galaxy on a once-in-a-lifetime joyride of companionship. and since more and more people join the races and it reaches out further and further, the Rainbow Road will only become more and more beautiful and epic.
      • And then it will become the highway between the stars.

Neo Bowser City is a new version of the City from the Super Mario Bros movie.
To me, both cities always had a style which was a little bit similar. Perhaps, in a future version of the track, the players might even encounter or be able to drive the Police cars http://www.smbmovie.com/SMBArchive/preproduction/artwork/7_art.html from the movie.
  • THAT MOVIE ISN'T EVEN CANON YOU TROPUS :/

Retro courses for Mario Kart 8...
Before the guesses begin, these are the seven retro tracks that have already been confirmed:
  • Mario Circuit (from Super Circuit)
  • Dry Dry Desert (from Double Dash!!)
  • Tick Tock Clock (from DS)
  • Grumble Volcano (from Wii)
  • Music Park (aka Melody Motorway, from 7)
  • Piranha Plant Slide (aka Piranha Plant Pipeway, from 7)
  • DK Jungle (from 7)
In my personal opinion, I think the Rainbow Road from 64 will reappear as the final course of the Lightning Cup, because the Rainbow Road from Super reappeared in 7. Well, it's possible.

  • Confirmed as of April 3, 2014. 64's Rainbow Road appears as the last course of the Lightning Cup.

Double Dash's Rainbow Road will appear in Mario Kart 9.
Well, SNES Rainbow Road appeared in 7, and 64's Rainbow Road is appearing in 8, so it would make sense that GCN Rainbow Road would appear in 9.
  • If they're going in order, then GBA Rainbow Road is next.
    • Assuming Mario Kart 9 will be the next handheld entry in the series, that is. Going off of that, GCN Rainbow Road could be saved for the Mario Kart game that hits the Wii U's successor.

The games are all part of some big off-screen adventure
     Kinda long 
The characters team up using the races as a distraction so that others can get close to whatever villain is threatening the world and act they like rivals to fool the bad guys, or some kind of time warp makes them repeat most sections of the road three times while they try to get to the villain. It would explain why Mario Peach and the rest don't seem to mind going karting with Bowser. The games always have at least one Mario Circuit, Bowser Castle, and Rainbow Road because they always start off actually racing at some stadium until they go to the castle when they first hear of trouble, and the villain sets up base at Bowser's castle, and the racers get sent to some rainbow-colored track in space, which seems to get bigger and more complex each game because the villain's plans do. The cups are long roads that eventually lead to Bowser's castle, and each one is blocked after the game it's in or they don't want to make it obvious by taking the same route each time. The retro tracks are a result of the big bad sending them back in time. The obsticals like Goombas, Chain Chomps, and Piranha Plants are Bowser's troops who defected to the enemy's side. The unlocked racers are captured characters that are rescued and the unlocked karts are built by an unseen engineer who also designed emblems and built R.O.B in DS and built custom karts and Metal Mario in 7. The babies from Double Dash and Wii were also brought to the present via time travel. Rainbow Road is some kind of world-destroying asteroid-like object that the racers send further into space and it gets bigger and stronger each time the bad guys bring it back. The closest it came to destroying everything was in Double Dash, where you could see Mushroom City below it. After Wii, it crashed into the moon but was slow enough to avoid doing much damage, which is why you drive on the moon and a planet similar to Saturn.
Knowing what Mario Kart 8 did with Mario Kart 64's Rainbow Road, there's a chance that if Wario Stadium (N64 Version), the only Mario Kart 64 course so far not to be in a Retro Track, would receive the same "3 Section" treatment
  • It is the second longest track in that game after all ...
Mario Kart 9 will not have Wario Stadium.
That will be saved for the game after that. Instead, Mario Kart 64 will be represented through Double Decker. Honestly, Wario Stadium is a really hard concept to modernize, since it was borne out of the Nintendo 64's limitations and would be pretty boring by today's standards, but it wouldn't make sense without the ultra-compact layout. I think the team will continue to think about how to get Wario Stadium to work (no doubt this is why they've held off on it for so long and why Yoshi Valley took so long) while fulfilling the rule of a Retro Course from every past Mario Kart game through the Battle Mode.
Diffrent colored Toads will be a reward for buying the next Mario Kart 8 DLC bundle.
Think about it we say different colored Shy Guys and Yoshis watching the races from the sidelines before the update. More over Toads have been given the same treatment in the Mario Baseball series where they along with Shy Guys and Yoshis in the second game were given alternate colors that the player could switch. Toad is also between the two one the roster with the only other character in between being Koopa who could also get the same treatment for the same reasons.
Super Mario Bros.WMG/Video GamesMario Kart 8

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