
Terrinam |
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Talking elsewhere about Bowser's villain cred got me to thinking about the relationship between him and Mario and the actions he does.
Between kidnapping Peach and his various attempts to gain power, it honestly does seem like he's undergone villain decay. Early on in the Super Mario series, he was treated as a serious threat that had to be countered with what amounted to a mushroom-powered superhuman.
By Super Mario RPG, he and Mario are simply bickering before the real threat shows up and he has to team up with Mario.
And ever since then, for the most part, it seems all of his schemes are either centered around his stalkerish crush on Peach, annoying Mario, or both at once.
I get why they can't simply remove him from the picture: Aside from how annoying he is to them, he is still the legitimate ruler of a kingdom and has a military at his command that has proven a very credible threat in the past. If they took him out, they're looking at war from his various children. Not a good scenario.
And yet, they go karting with Bowser. They invite him to participate in sports. They invite him to play party games. You really get the feeling that when he's not kidnapping Peach or trolling Mario, the three of them are hanging out and generally friends.
Plus, the brawls themselves. Spinning Bowser in a circle to launch him? Dropping him in lava, which he has demonstrated repeated immunity to? And him accepting these as defeats? It's almost like the pair are not seriously fighting, but just having a brawl because of Bowser's latest bit of being annoying. It's almost like they're siblings.
And Peach quite clearly isn't interested in either of them romantically, yet she constantly puts up with Bowser kidnapping her and Bowser and Mario brawling over her.
And that's when the idea occurred to me. They are siblings. Not of blood, but after all of the things they have done together, the pair have gone from sworn enemies to blood brothers. When there isn't a serious threat, they act as they always will; Bowser is an annoying troll, Mario rolls his eyes and heads to kick Bowser's rear again.
Peach fits in because I think she is entertained by it all. Ruling a kingdom has to be boring most of the time. And she has repeatedly shown she can hold her own in a fight, so there's really no reason for her to play damsel as she does. Unless, of course, she does it because whatever Bowser's latest scheme is, it'll be entertaining. Bowser's kidnappings and Mario's rescues break up the monotony of ruling the Mushroom Kingdom.
And the rest of the time they drop the facade of their long-term relationships and focus just on enjoying the time they spend together. Like any family would.

The Sideromancer |
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Bowser definitely considers Mario to be his rival, perhaps the only person he considers a worthy opponent. He states as much in Galaxy, and in the remake of 64, he only allows mario and not any of the other three playable characters into the final fight.
There have been a couple other schemes based on expanding his reach (3d world comes to mind), but even in these, it mostly seems that he's playing the part of your average Roman general, making sure his veterans have a place to settle.
As for being a credible military threat, that's certainly true. Any look at the combined firepower of Bowser's army in comparison to anything else since at least SMB3 (when he first got tanks)could tell you that if he was interested in pillaging, there wouldn't be a whole lot left standing (given the logistics of the fewer-than-ten beings proven to be capable of fighting him against an army).
Another interesting possibility as to why he wants peach so badly: He likely grew up unfamiliar with his parents (if nothing else, they probably would have been invited to at least one marriage). He's trying to make sure his son can grow up with both parents there for him.

SynchroniciticallyChallenged |
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This may shed some light on bowser's mommy issues.
Oddly enough, she was invited to his wedding day before mario wrecked the chance. Awesome show. Love the 90's. To support the 'blood brother' theory, the entire show is like a stage play with costumes where nearly everyone is in on the gag. Much like the gentry and nobles playing chess with live pawns.

Terrinam |

I think the following also adds some weight to it.
I kinda wonder if, maybe, his plan was to let Mario steal one of his small airships, only for it to change when he realized Mario had a hat person and a way off the island through the hat's abilities. Maybe, maybe not; he could have just been counting on Mario's general resourcefulness.
Then, comes the Cloud Kingdom fight. Bowser basically ambushes Mario with his airship, and then waits around for Mario to engage him in an arena. And as this is going on, you get a shot of Peach standing still and holding a bouquet of piranha plants. And Peach doesn't even look the least bit concerned; if anything, she almost seems bored.
Bowser gets beaten, is back on his airship, and promptly demonstrates something we all know he has: Military dominance. He promptly blows Mario and Mario's airship out of the sky, and there's nothing Mario can even do to counter it. He demonstrates that if he were actually serious about making certain Mario couldn't stop him, he could have taken Mario out of the fight clear back in the Sand Kingdom by destroying Mario's airship and married Peach without any worries of Mario stopping him.
Top it all off, Bowser is not using anything close to the forces he used against the Mushroom Kingdom in the past, yet he still easily curbstomps every single kingdom up until Mario comes along.
So Bowser very much not only remains a serious military power, but also is a much greater threat to Mario now than he was when the two first met. Yet, save for rare instances, he doesn't act on the capacity.
It really does seem like Bowser is not trying to stop Mario.